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user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:%E5%88%9B%E5%BB%BA%E8%B4%A6%E6%88%B7&returnto=%E8%8B%AF%E9%85%9A" title="我们推荐您创建账号并登录，但这不是强制性的" class=""><span>创建账号</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:%E7%94%A8%E6%88%B7%E7%99%BB%E5%BD%95&returnto=%E8%8B%AF%E9%85%9A" title="建议你登录，尽管并非必须。[o]" accesskey="o" class=""><span>登录</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="更多选项" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="个人工具" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" 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mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>创建账号</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:%E7%94%A8%E6%88%B7%E7%99%BB%E5%BD%95&returnto=%E8%8B%AF%E9%85%9A" title="建议你登录，尽管并非必须。[o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>登录</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> 未登录编辑者的页面 <a href="/wiki/Help:%E6%96%B0%E6%89%8B%E5%85%A5%E9%97%A8" aria-label="了解有关编辑的更多信息"><span>了解详情</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:%E6%88%91%E7%9A%84%E8%B4%A1%E7%8C%AE" title="来自此IP地址的编辑列表[y]" accesskey="y"><span>贡献</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:%E6%88%91%E7%9A%84%E8%AE%A8%E8%AE%BA%E9%A1%B5" title="对于来自此IP地址编辑的讨论[n]" accesskey="n"><span>讨论</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="站点"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="目录" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">目录</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">移至侧栏</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">隐藏</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">序言</div> </a> </li> <li id="toc-发现" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#发现"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>发现</span> </div> </a> <ul id="toc-发现-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-结构" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#结构"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>结构</span> </div> </a> <ul id="toc-结构-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-物理性质" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#物理性质"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>物理性质</span> </div> </a> <ul id="toc-物理性质-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-化学性质" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#化学性质"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>化学性质</span> </div> </a> <ul id="toc-化学性质-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-制备" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#制备"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>制备</span> </div> </a> <ul id="toc-制备-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-安全" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#安全"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>安全</span> </div> </a> <ul id="toc-安全-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-工业及醫學用途" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#工业及醫學用途"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>工业及醫學用途</span> </div> </a> <ul id="toc-工业及醫學用途-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-衍生物" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#衍生物"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>衍生物</span> </div> </a> <ul id="toc-衍生物-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-参见" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#参见"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>参见</span> </div> </a> <ul id="toc-参见-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-註釋" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#註釋"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>註釋</span> </div> </a> <ul id="toc-註釋-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-参考文献" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#参考文献"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>参考文献</span> </div> </a> <ul id="toc-参考文献-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="目录" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="开关目录" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">开关目录</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">苯酚</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="前往另一种语言写成的文章。83种语言可用" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-83" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">83种语言</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Fenol" title="Fenol – 南非荷兰语" lang="af" hreflang="af" data-title="Fenol" data-language-autonym="Afrikaans" data-language-local-name="南非荷兰语" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%8A%D9%86%D9%88%D9%84" title="فينول – 阿拉伯语" lang="ar" hreflang="ar" data-title="فينول" data-language-autonym="العربية" data-language-local-name="阿拉伯语" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Fenol" title="Fenol – 阿斯图里亚斯语" lang="ast" hreflang="ast" data-title="Fenol" data-language-autonym="Asturianu" data-language-local-name="阿斯图里亚斯语" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Fenol" title="Fenol – 阿塞拜疆语" lang="az" hreflang="az" data-title="Fenol" data-language-autonym="Azərbaycanca" data-language-local-name="阿塞拜疆语" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D9%86%D9%88%D9%84" title="فنول – South Azerbaijani" lang="azb" hreflang="azb" data-title="فنول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ba mw-list-item"><a href="https://ba.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – 巴什基尔语" lang="ba" hreflang="ba" data-title="Фенол" data-language-autonym="Башҡортса" data-language-local-name="巴什基尔语" class="interlanguage-link-target"><span>Башҡортса</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – 白俄罗斯语" lang="be" hreflang="be" data-title="Фенол" data-language-autonym="Беларуская" data-language-local-name="白俄罗斯语" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – 保加利亚语" lang="bg" hreflang="bg" data-title="Фенол" data-language-autonym="Български" data-language-local-name="保加利亚语" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AB%E0%A7%87%E0%A6%A8%E0%A6%B2" title="ফেনল – 孟加拉语" lang="bn" hreflang="bn" data-title="ফেনল" data-language-autonym="বাংলা" data-language-local-name="孟加拉语" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Fenol" title="Fenol – 波斯尼亚语" lang="bs" hreflang="bs" data-title="Fenol" data-language-autonym="Bosanski" data-language-local-name="波斯尼亚语" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fenol" title="Fenol – 加泰罗尼亚语" lang="ca" hreflang="ca" data-title="Fenol" data-language-autonym="Català" data-language-local-name="加泰罗尼亚语" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cdo mw-list-item"><a href="https://cdo.wikipedia.org/wiki/G%C4%83-p%C5%8F%CC%A4-l%C4%ADk-k%C3%A1ik-s%C5%8Fng" title="Gă-pŏ̤-lĭk-káik-sŏng – Mindong" lang="cdo" hreflang="cdo" data-title="Gă-pŏ̤-lĭk-káik-sŏng" data-language-autonym="閩東語 / Mìng-dĕ̤ng-ngṳ̄" data-language-local-name="Mindong" class="interlanguage-link-target"><span>閩東語 / Mìng-dĕ̤ng-ngṳ̄</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Fenol" title="Fenol – 捷克语" lang="cs" hreflang="cs" data-title="Fenol" data-language-autonym="Čeština" data-language-local-name="捷克语" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-csb mw-list-item"><a href="https://csb.wikipedia.org/wiki/Karb%C3%B3l" title="Karból – 卡舒比语" lang="csb" hreflang="csb" data-title="Karból" data-language-autonym="Kaszëbsczi" data-language-local-name="卡舒比语" class="interlanguage-link-target"><span>Kaszëbsczi</span></a></li><li class="interlanguage-link interwiki-cv mw-list-item"><a href="https://cv.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BB_%D0%B9%C3%BF%C3%A7%D0%B5%D0%BA%C4%95" title="Карбол йÿçекĕ – 楚瓦什语" lang="cv" hreflang="cv" data-title="Карбол йÿçекĕ" data-language-autonym="Чӑвашла" data-language-local-name="楚瓦什语" class="interlanguage-link-target"><span>Чӑвашла</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Ffenol" title="Ffenol – 威尔士语" lang="cy" hreflang="cy" data-title="Ffenol" data-language-autonym="Cymraeg" data-language-local-name="威尔士语" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Fenol" title="Fenol – 丹麦语" lang="da" hreflang="da" data-title="Fenol" data-language-autonym="Dansk" data-language-local-name="丹麦语" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phenol" title="Phenol – 德语" lang="de" hreflang="de" data-title="Phenol" data-language-autonym="Deutsch" data-language-local-name="德语" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A6%CE%B1%CE%B9%CE%BD%CF%8C%CE%BB%CE%B7" title="Φαινόλη – 希腊语" lang="el" hreflang="el" data-title="Φαινόλη" data-language-autonym="Ελληνικά" data-language-local-name="希腊语" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Phenol" title="Phenol – 英语" lang="en" hreflang="en" data-title="Phenol" data-language-autonym="English" data-language-local-name="英语" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Fenolo" title="Fenolo – 世界语" lang="eo" hreflang="eo" data-title="Fenolo" data-language-autonym="Esperanto" data-language-local-name="世界语" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Fenol" title="Fenol – 西班牙语" lang="es" hreflang="es" data-title="Fenol" data-language-autonym="Español" data-language-local-name="西班牙语" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Fenool" title="Fenool – 爱沙尼亚语" lang="et" hreflang="et" data-title="Fenool" data-language-autonym="Eesti" data-language-local-name="爱沙尼亚语" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Fenol" title="Fenol – 巴斯克语" lang="eu" hreflang="eu" data-title="Fenol" data-language-autonym="Euskara" data-language-local-name="巴斯克语" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D9%86%D9%88%D9%84" title="فنول – 波斯语" lang="fa" hreflang="fa" data-title="فنول" data-language-autonym="فارسی" data-language-local-name="波斯语" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Fenoli" title="Fenoli – 芬兰语" lang="fi" hreflang="fi" data-title="Fenoli" data-language-autonym="Suomi" data-language-local-name="芬兰语" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Phenol" title="Phenol – 法罗语" lang="fo" hreflang="fo" data-title="Phenol" data-language-autonym="Føroyskt" data-language-local-name="法罗语" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ph%C3%A9nol_(compos%C3%A9)" title="Phénol (composé) – 法语" lang="fr" hreflang="fr" data-title="Phénol (composé)" data-language-autonym="Français" data-language-local-name="法语" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/Fenol" title="Fenol – 西弗里西亚语" lang="fy" hreflang="fy" data-title="Fenol" data-language-autonym="Frysk" data-language-local-name="西弗里西亚语" class="interlanguage-link-target"><span>Frysk</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Fean%C3%B3l" title="Feanól – 爱尔兰语" lang="ga" hreflang="ga" data-title="Feanól" data-language-autonym="Gaeilge" data-language-local-name="爱尔兰语" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Fenol" title="Fenol – 加利西亚语" lang="gl" hreflang="gl" data-title="Fenol" data-language-autonym="Galego" data-language-local-name="加利西亚语" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%A0%D7%95%D7%9C" title="פנול – 希伯来语" lang="he" hreflang="he" data-title="פנול" data-language-autonym="עברית" data-language-local-name="希伯来语" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AB%E0%A4%BF%E0%A4%A8%E0%A5%8B%E0%A4%B2" title="फिनोल – 印地语" lang="hi" hreflang="hi" data-title="फिनोल" data-language-autonym="हिन्दी" data-language-local-name="印地语" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Fenol" title="Fenol – 克罗地亚语" lang="hr" hreflang="hr" data-title="Fenol" data-language-autonym="Hrvatski" data-language-local-name="克罗地亚语" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Fenol" title="Fenol – 匈牙利语" lang="hu" hreflang="hu" data-title="Fenol" data-language-autonym="Magyar" data-language-local-name="匈牙利语" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%96%D5%A5%D5%B6%D5%B8%D5%AC" title="Ֆենոլ – 亚美尼亚语" lang="hy" hreflang="hy" data-title="Ֆենոլ" data-language-autonym="Հայերեն" data-language-local-name="亚美尼亚语" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Fenol" title="Fenol – 印度尼西亚语" lang="id" hreflang="id" data-title="Fenol" data-language-autonym="Bahasa Indonesia" data-language-local-name="印度尼西亚语" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Fenolo" title="Fenolo – 伊多语" lang="io" hreflang="io" data-title="Fenolo" data-language-autonym="Ido" data-language-local-name="伊多语" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Fenolo" title="Fenolo – 意大利语" lang="it" hreflang="it" data-title="Fenolo" data-language-autonym="Italiano" data-language-local-name="意大利语" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A7%E3%83%8E%E3%83%BC%E3%83%AB" title="フェノール – 日语" lang="ja" hreflang="ja" data-title="フェノール" data-language-autonym="日本語" data-language-local-name="日语" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/F%C3%A9nol" title="Fénol – 爪哇语" lang="jv" hreflang="jv" data-title="Fénol" data-language-autonym="Jawa" data-language-local-name="爪哇语" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A4%E1%83%94%E1%83%9C%E1%83%9D%E1%83%9A%E1%83%98" title="ფენოლი – 格鲁吉亚语" lang="ka" hreflang="ka" data-title="ფენოლი" data-language-autonym="ქართული" data-language-local-name="格鲁吉亚语" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kaa mw-list-item"><a href="https://kaa.wikipedia.org/wiki/Fenol" title="Fenol – 卡拉卡尔帕克语" lang="kaa" hreflang="kaa" data-title="Fenol" data-language-autonym="Qaraqalpaqsha" data-language-local-name="卡拉卡尔帕克语" class="interlanguage-link-target"><span>Qaraqalpaqsha</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – 哈萨克语" lang="kk" hreflang="kk" data-title="Фенол" data-language-autonym="Қазақша" data-language-local-name="哈萨克语" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8E%98%EB%86%80" title="페놀 – 韩语" lang="ko" hreflang="ko" data-title="페놀" data-language-autonym="한국어" data-language-local-name="韩语" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – 柯尔克孜语" lang="ky" hreflang="ky" data-title="Фенол" data-language-autonym="Кыргызча" data-language-local-name="柯尔克孜语" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Phenolum" title="Phenolum – 拉丁语" lang="la" hreflang="la" data-title="Phenolum" data-language-autonym="Latina" data-language-local-name="拉丁语" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Fenolis" title="Fenolis – 立陶宛语" lang="lt" hreflang="lt" data-title="Fenolis" data-language-autonym="Lietuvių" data-language-local-name="立陶宛语" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Fenols" title="Fenols – 拉脱维亚语" lang="lv" hreflang="lv" data-title="Fenols" data-language-autonym="Latviešu" data-language-local-name="拉脱维亚语" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – 马其顿语" lang="mk" hreflang="mk" data-title="Фенол" data-language-autonym="Македонски" data-language-local-name="马其顿语" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AB%E0%B5%80%E0%B4%A8%E0%B5%8B%E0%B5%BE" title="ഫീനോൾ – 马拉雅拉姆语" lang="ml" hreflang="ml" data-title="ഫീനോൾ" data-language-autonym="മലയാളം" data-language-local-name="马拉雅拉姆语" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-mr mw-list-item"><a href="https://mr.wikipedia.org/wiki/%E0%A4%AB%E0%A5%87%E0%A4%A8%E0%A5%89%E0%A4%B2" title="फेनॉल – 马拉地语" lang="mr" hreflang="mr" data-title="फेनॉल" data-language-autonym="मराठी" data-language-local-name="马拉地语" class="interlanguage-link-target"><span>मराठी</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Fenol" title="Fenol – 马来语" lang="ms" hreflang="ms" data-title="Fenol" data-language-autonym="Bahasa Melayu" data-language-local-name="马来语" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%80%E1%80%AC%E1%80%98%E1%80%B1%E1%80%AC%E1%80%BA%E1%80%9C%E1%80%85%E1%80%BA%E1%80%A1%E1%80%80%E1%80%BA%E1%80%86%E1%80%85%E1%80%BA" title="ကာဘော်လစ်အက်ဆစ် – 缅甸语" lang="my" hreflang="my" data-title="ကာဘော်လစ်အက်ဆစ်" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="缅甸语" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fenol" title="Fenol – 荷兰语" lang="nl" hreflang="nl" data-title="Fenol" data-language-autonym="Nederlands" data-language-local-name="荷兰语" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Fenol" title="Fenol – 书面挪威语" lang="nb" hreflang="nb" data-title="Fenol" data-language-autonym="Norsk bokmål" data-language-local-name="书面挪威语" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fenol" title="Fenol – 波兰语" lang="pl" hreflang="pl" data-title="Fenol" data-language-autonym="Polski" data-language-local-name="波兰语" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D9%81%DB%8C%D9%86%D9%88%D9%84" title="فینول – Western Punjabi" lang="pnb" hreflang="pnb" data-title="فینول" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Fenol" title="Fenol – 葡萄牙语" lang="pt" hreflang="pt" data-title="Fenol" data-language-autonym="Português" data-language-local-name="葡萄牙语" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Fenol" title="Fenol – 罗马尼亚语" lang="ro" hreflang="ro" data-title="Fenol" data-language-autonym="Română" data-language-local-name="罗马尼亚语" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – 俄语" lang="ru" hreflang="ru" data-title="Фенол" data-language-autonym="Русский" data-language-local-name="俄语" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/%C3%80citu_f%C3%A8nicu" title="Àcitu fènicu – 西西里语" lang="scn" hreflang="scn" data-title="Àcitu fènicu" data-language-autonym="Sicilianu" data-language-local-name="西西里语" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Phenol" title="Phenol – 苏格兰语" lang="sco" hreflang="sco" data-title="Phenol" data-language-autonym="Scots" data-language-local-name="苏格兰语" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Fenol" title="Fenol – 塞尔维亚-克罗地亚语" lang="sh" hreflang="sh" data-title="Fenol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="塞尔维亚-克罗地亚语" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Phenol" title="Phenol – Simple English" lang="en-simple" hreflang="en-simple" data-title="Phenol" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Fenol" title="Fenol – 斯洛伐克语" lang="sk" hreflang="sk" data-title="Fenol" data-language-autonym="Slovenčina" data-language-local-name="斯洛伐克语" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Fenol" title="Fenol – 斯洛文尼亚语" lang="sl" hreflang="sl" data-title="Fenol" data-language-autonym="Slovenščina" data-language-local-name="斯洛文尼亚语" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Fenolet" title="Fenolet – 阿尔巴尼亚语" lang="sq" hreflang="sq" data-title="Fenolet" data-language-autonym="Shqip" data-language-local-name="阿尔巴尼亚语" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Fenol" title="Fenol – 塞尔维亚语" lang="sr" hreflang="sr" data-title="Fenol" data-language-autonym="Српски / srpski" data-language-local-name="塞尔维亚语" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Fenol" title="Fenol – 瑞典语" lang="sv" hreflang="sv" data-title="Fenol" data-language-autonym="Svenska" data-language-local-name="瑞典语" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AF%80%E0%AE%A9%E0%AE%BE%E0%AE%B2%E0%AF%8D" title="பீனால் – 泰米尔语" lang="ta" hreflang="ta" data-title="பீனால்" data-language-autonym="தமிழ்" data-language-local-name="泰米尔语" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – 塔吉克语" lang="tg" hreflang="tg" data-title="Фенол" data-language-autonym="Тоҷикӣ" data-language-local-name="塔吉克语" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9F%E0%B8%B5%E0%B8%99%E0%B8%AD%E0%B8%A5" title="ฟีนอล – 泰语" lang="th" hreflang="th" data-title="ฟีนอล" data-language-autonym="ไทย" data-language-local-name="泰语" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Phenol" title="Phenol – 他加禄语" lang="tl" hreflang="tl" data-title="Phenol" data-language-autonym="Tagalog" data-language-local-name="他加禄语" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Fenol" title="Fenol – 土耳其语" lang="tr" hreflang="tr" data-title="Fenol" data-language-autonym="Türkçe" data-language-local-name="土耳其语" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%BE%D0%BB" title="Фенол – 乌克兰语" lang="uk" hreflang="uk" data-title="Фенол" data-language-autonym="Українська" data-language-local-name="乌克兰语" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%81%DB%8C%D9%86%D9%88%D9%84" title="فینول – 乌尔都语" lang="ur" hreflang="ur" data-title="فینول" data-language-autonym="اردو" data-language-local-name="乌尔都语" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Fenol" title="Fenol – 乌兹别克语" lang="uz" hreflang="uz" data-title="Fenol" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="乌兹别克语" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Phenol" title="Phenol – 越南语" lang="vi" hreflang="vi" data-title="Phenol" data-language-autonym="Tiếng Việt" data-language-local-name="越南语" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Phenol" title="Phenol – 瓦瑞语" lang="war" hreflang="war" data-title="Phenol" data-language-autonym="Winaray" data-language-local-name="瓦瑞语" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%8B%AF%E9%85%9A" title="苯酚 – 吴语" lang="wuu" hreflang="wuu" data-title="苯酚" data-language-autonym="吴语" data-language-local-name="吴语" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Phenol" title="Phenol – 闽南语" lang="nan" hreflang="nan" data-title="Phenol" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="闽南语" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%8B%AF%E9%85%9A" title="苯酚 – 粤语" lang="yue" hreflang="yue" data-title="苯酚" data-language-autonym="粵語" data-language-local-name="粤语" class="interlanguage-link-target"><span>粵語</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q130336#sitelinks-wikipedia" title="编辑跨语言链接" class="wbc-editpage">编辑链接</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="命名空间"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div 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</div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="页面工具"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="外观"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">外观</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" 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.mbox-text-span{margin-left:23px!important}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ambox{border-left-color:#36c!important}html.skin-theme-clientpref-night .mw-parser-output .ambox-speedy,html.skin-theme-clientpref-night .mw-parser-output .ambox-delete{border-left-color:#b32424!important}html.skin-theme-clientpref-night .mw-parser-output .ambox-speedy{background-color:#300!important}html.skin-theme-clientpref-night .mw-parser-output .ambox-content{border-left-color:#f28500!important}html.skin-theme-clientpref-night .mw-parser-output .ambox-style{border-left-color:#fc3!important}html.skin-theme-clientpref-night .mw-parser-output .ambox-move{border-left-color:#9932cc!important}html.skin-theme-clientpref-night .mw-parser-output .ambox-protection{border-left-color:#a2a9b1!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ambox{border-left-color:#36c!important}html.skin-theme-clientpref-os .mw-parser-output .ambox-speedy,html.skin-theme-clientpref-os .mw-parser-output .ambox-delete{border-left-color:#b32424!important}html.skin-theme-clientpref-os .mw-parser-output .ambox-speedy{background-color:#300!important}html.skin-theme-clientpref-os .mw-parser-output .ambox-content{border-left-color:#f28500!important}html.skin-theme-clientpref-os .mw-parser-output .ambox-style{border-left-color:#fc3!important}html.skin-theme-clientpref-os .mw-parser-output .ambox-move{border-left-color:#9932cc!important}html.skin-theme-clientpref-os .mw-parser-output .ambox-protection{border-left-color:#a2a9b1!important}}</style><table class="box-Expert_needed plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div style="width:52px"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Ambox_important.svg/40px-Ambox_important.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Ambox_important.svg/60px-Ambox_important.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Ambox_important.svg/80px-Ambox_important.svg.png 2x" data-file-width="40" data-file-height="40" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">此條目需要<b>精通或熟悉<a href="/wiki/%E5%8C%96%E5%AD%A6" class="mw-redirect" title="化学">化学</a>的编者</b>参与及协助编辑。<span class="hide-when-compact"></span> <small class="date-container"><i>(<span class="date">2020年6月26日</span>)</i></small><span class="hide-when-compact"><br /><small>請<a href="/wiki/Wikipedia:%E5%B0%88%E5%AE%B6%E9%82%80%E8%AB%8B%E5%B7%A5%E4%BD%9C%E5%B0%8F%E7%B5%84" title="Wikipedia:專家邀請工作小組">邀請</a>適合的人士<a class="external text" href="https://zh.wikipedia.org/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit">改善本条目</a>。更多的細節與詳情請參见<a href="/wiki/Talk:%E8%8B%AF%E9%85%9A" title="Talk:苯酚">討論頁</a>。<br />另見其他<a href="/wiki/Category:%E9%9C%80%E8%A6%81%E5%8C%96%E5%AD%A6%E4%B8%93%E5%AE%B6%E5%85%B3%E6%B3%A8%E7%9A%84%E9%A1%B5%E9%9D%A2" title="Category:需要化学专家关注的页面">需要化学專家關注的頁面</a>。</small></span><span class="hide-when-compact"></span></div></td></tr></tbody></table> <div id="noteTA-f062df7d" class="noteTA"><div class="noteTA-group"><div data-noteta-group-source="module" data-noteta-group="Medicine"></div><div data-noteta-group-source="module" data-noteta-group="Chemistry"></div></div></div> <style data-mw-deduplicate="TemplateStyles:r85099211">.mw-parser-output .hatnote{font-size:small}.mw-parser-output div.hatnote{padding-left:2em;margin-bottom:0.8em;margin-top:0.8em}.mw-parser-output .hatnote-notice-img::after{content:"\202f \202f \202f \202f "}.mw-parser-output .hatnote-notice-img-small::after{content:"\202f \202f "}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}body.skin-minerva .mw-parser-output .hatnote-notice-img,body.skin-minerva .mw-parser-output .hatnote-notice-img-small{display:none}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable selfref"><span typeof="mw:File"><a href="/wiki/File:Star_of_life_caution.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Star_of_life_caution.svg/20px-Star_of_life_caution.svg.png" decoding="async" width="20" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Star_of_life_caution.svg/30px-Star_of_life_caution.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Star_of_life_caution.svg/40px-Star_of_life_caution.svg.png 2x" data-file-width="210" data-file-height="190" /></a></span> <a href="/wiki/%E7%BB%B4%E5%9F%BA%E7%99%BE%E7%A7%91" title="维基百科">维基百科</a>中的醫學内容<b>仅供参考</b>，並<b>不能</b>視作專業意見。如需獲取醫療幫助或意見，请咨询专业人士。詳見<b><a href="/wiki/Wikipedia:%E5%8C%BB%E5%AD%A6%E5%A3%B0%E6%98%8E" title="Wikipedia:医学声明">醫學聲明</a></b>。</div> <style data-mw-deduplicate="TemplateStyles:r84001320">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox nounderlines" cellspacing="0" cellpadding="3" rules="all" style="background-color:#f0f0f0; float:right; margin: 0 0 1em 1em; border-color: #aaaaaa; border-style:solid; border:1px; border-collapse:collapse; empty-cells:show; width:305px; font-size:90%;"> <tbody><tr> <th colspan="2" style="font-size:120%; text-align:center; background:#d6e0dc;">苯酚 </th></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"> <table class="borderless"> <tbody><tr> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Phenol2.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Phenol2.svg/67px-Phenol2.svg.png" decoding="async" width="67" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Phenol2.svg/101px-Phenol2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Phenol2.svg/134px-Phenol2.svg.png 2x" data-file-width="70" data-file-height="128" /></a><figcaption></figcaption></figure> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Phenol-2D-skeletal.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/Phenol-2D-skeletal.png/75px-Phenol-2D-skeletal.png" decoding="async" width="75" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/Phenol-2D-skeletal.png/113px-Phenol-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/91/Phenol-2D-skeletal.png/150px-Phenol-2D-skeletal.png 2x" data-file-width="646" data-file-height="1100" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"> <table class="borderless"> <tbody><tr> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Phenol-3D-balls.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Phenol-3D-balls.png/100px-Phenol-3D-balls.png" decoding="async" width="100" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Phenol-3D-balls.png/150px-Phenol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Phenol-3D-balls.png/200px-Phenol-3D-balls.png 2x" data-file-width="942" data-file-height="1100" /></a><figcaption></figcaption></figure> </td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Phenol-3D-vdW.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Phenol-3D-vdW.png/100px-Phenol-3D-vdW.png" decoding="async" width="100" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Phenol-3D-vdW.png/150px-Phenol-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Phenol-3D-vdW.png/200px-Phenol-3D-vdW.png 2x" data-file-width="971" data-file-height="1100" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><a href="/wiki/File:Phenol_2_grams.jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Phenol_2_grams.jpg/220px-Phenol_2_grams.jpg" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Phenol_2_grams.jpg/330px-Phenol_2_grams.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Phenol_2_grams.jpg/440px-Phenol_2_grams.jpg 2x" data-file-width="500" data-file-height="500" /></a></span> </td></tr> <tr> <td colspan="2" style="max-width:305px; word-wrap: break-word; text-align: center;"><a href="/wiki/IUPAC%E5%91%BD%E5%90%8D%E6%B3%95" title="IUPAC命名法">IUPAC名</a><br />Hydroxybenzene<br />羥基苯 </td></tr> <tr> <td>别名 </td> <td>石炭酸 </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">识别 </th></tr> <tr> <td><a href="/wiki/CAS%E5%8F%B7" title="CAS号">CAS号</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=108-95-2">108-95-2</a></span> <sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup> </td></tr> <tr> <td><a href="/wiki/PubChem" title="PubChem">PubChem</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/996">996</a></span> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://www.chemspider.com/971">971</a></span> </td></tr> <tr> <td><a href="/wiki/SMILES" class="mw-redirect" title="SMILES">SMILES</a> </td> <td><div style="word-break:break-all;"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div> </div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0;"><li style="line-height: inherit; margin: 0"><span lang="en">Oc1ccccc1</span></li></ul> </div></div> </td></tr> <tr> <td><a href="/wiki/%E5%9B%BD%E9%99%85%E5%8C%96%E5%90%88%E7%89%A9%E6%A0%87%E8%AF%86" title="国际化合物标识">InChI</a> </td> <td><div style="word-break:break-all;"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div> </div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0;"><li style="line-height: inherit; margin: 0">1/C6H6O/c7-6-<br />4-2-1-3-5-6/h1-5,7H</li></ul> </div></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15882">15882</a></span> </td></tr> <tr> <td><a href="/wiki/%E5%8C%96%E5%AD%A6%E7%89%A9%E8%B4%A8%E6%AF%92%E6%80%A7%E6%95%B0%E6%8D%AE%E5%BA%93" title="化学物质毒性数据库">RTECS</a> </td> <td>SJ3325000 </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://www.drugbank.ca/cgi-bin/show_drug.cgi?CARD=DB03255">DB03255</a></span> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://www.genome.ad.jp/dbget-bin/www_bget?cpd:D06536">D06536</a></span> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">性质 </th></tr> <tr> <td><a href="/wiki/%E5%8C%96%E5%AD%A6%E5%BC%8F" title="化学式">化学式</a> </td> <td><span lang="en">C<sub>6</sub>H<sub>5</sub>OH</span> </td></tr> <tr> <td><a href="/wiki/%E6%91%A9%E5%B0%94%E8%B4%A8%E9%87%8F" title="摩尔质量">摩尔质量</a> </td> <td>94.11 g·mol⁻¹ </td></tr> <tr> <td>外观 </td> <td>無色结晶状固体 </td></tr> <tr> <td><a href="/wiki/%E5%AF%86%E5%BA%A6" title="密度">密度</a> </td> <td>1.07 g/cm³ </td></tr> <tr> <td><a href="/wiki/%E7%86%94%E7%82%B9" title="熔点">熔点</a> </td> <td>40.5 °C </td></tr> <tr> <td><a href="/wiki/%E6%B2%B8%E7%82%B9" title="沸点">沸点</a> </td> <td>181.7 °C </td></tr> <tr> <td><a href="/wiki/%E6%BA%B6%E8%A7%A3%E6%80%A7" class="mw-redirect" title="溶解性">溶解性</a>（<a href="/wiki/%E6%B0%B4" title="水">水</a>） </td> <td>8.3 g/100 ml (20 °C) </td></tr> <tr> <td><a href="/wiki/%E9%85%B8%E5%BA%A6%E7%B3%BB%E6%95%B0" title="酸度系数">p<i>K</i><sub>a</sub></a> </td> <td><span lang="en">9.95</span> </td></tr> <tr> <td><a href="/wiki/%E5%81%B6%E6%A5%B5%E5%AD%90#分子的電偶極矩" title="偶極子">偶极矩</a> </td> <td>1.7 <a href="/wiki/%E5%BE%B7%E6%8B%9C" title="德拜">D</a> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">危险性 </th></tr> <tr> <td><a href="/wiki/%E5%8D%B1%E9%99%A9%E7%89%A9%E8%B4%A8%E7%9A%84%E5%88%86%E7%B1%BB%E3%80%81%E5%8C%85%E8%A3%85%E3%80%81%E6%A0%87%E7%A4%BA%E6%8C%87%E4%BB%A4" class="mw-redirect" title="危险物质的分类、包装、标示指令">欧盟分类</a> </td> <td>有毒 (<b>T</b>)<br /><a href="/wiki/%E7%AA%81%E5%8F%98%E5%8E%9F" class="mw-redirect" title="突变原">突变原</a><br />腐蚀性 (<b>C</b>) </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704">NFPA 704</a> </td> <td> <div style="position: relative; height: 85px; width: 75px;"> <div style="position: absolute; height: 75px; width: 75px;"><span typeof="mw:File"><a href="/wiki/File:NFPA_704.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/75px-NFPA_704.svg.png" decoding="async" width="75" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/113px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/150px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span></div> <div title="可燃性" style="background: transparent; width: 75px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 3px; font-size: large;"><span class="abbr" style="color: black;" title="可燃性2級。略爲加熱或暴露在高溫環境中可能被引燃（如柴油）。閃點在38 - 93°C。"><b>2</b></span></div> <div title="健康" style="background: transparent; width: 37.5px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 21px; font-size: large;"><span class="abbr" style="color: black;" title="健康危險3級。短時間的暴露可能導致嚴重的暫時性或持續性傷害（如氯氣）。"><b>3</b></span></div> <div title="反應性" style="background: transparent; width: 37.5px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 21px; left: 37.5px; font-size: large;"><span class="abbr" style="color: black;" title="反應性0級。通常情況下穩定，即使暴露於明火中也不反應，並且不與水反應（如液氮）。"><b>0</b></span></div> <div title="其它危險" style="background: transparent; width: 75px; height: 2em; text-align: center; vertical-align: middle; position: absolute; top: 44px; font-size: small;"><span class="abbr" style="color: black;" title="腐蝕性、強酸或強鹼（如硫酸、氫氧化鉀）"><b>COR</b></span></div> </div> </td></tr> <tr> <td><a href="/wiki/%E9%97%AA%E7%82%B9" title="闪点">闪点</a> </td> <td>79 °C </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">相关物质 </th></tr> <tr> <td>相关化学品 </td> <td><a href="/wiki/%E8%8B%AF%E7%A1%AB%E9%85%9A" title="苯硫酚">苯硫酚</a>、<a href="/wiki/%E8%8B%AF%E7%A1%92%E9%85%9A" title="苯硒酚">苯硒酚</a>、<a href="/wiki/%E8%8B%AF%E7%A2%B2%E9%85%9A" title="苯碲酚">苯碲酚</a> </td></tr> <tr> <td style="background:#D6E0DC; text-align:center;" colspan="2">若非注明，所有数据均出自<a href="/wiki/%E6%A0%87%E5%87%86%E7%8A%B6%E6%80%81" title="标准状态">标准状态（25 ℃，100 kPa）</a>下。 </td></tr></tbody></table> <p><b>苯酚</b>（phenol）又名<b>石炭酸</b>（carbolic acid）、<b>羟基苯</b>（hydroxybenzene）、<b>苯醇</b>（benzenol）、<b>酚酸</b>（phenolic acid）等，是最简单的<a href="/wiki/%E9%85%9A" title="酚">酚</a>类<a href="/wiki/%E6%9C%89%E6%9C%BA%E7%89%A9" class="mw-redirect" title="有机物">有机物</a>，化学式 <span class="chemf nowrap">C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>H<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />5</span>OH</span>（PhOH），常温下为一种无色针状晶体。具毒性、弱酸性，易<a href="/wiki/%E6%BD%AE%E8%A7%A3" title="潮解">潮解</a>。 </p><p>苯酚是一种常见的化学品，是生产某些<a href="/wiki/%E6%A0%91%E8%84%82" title="树脂">树脂</a>、<a href="/wiki/%E6%9D%80%E8%8F%8C%E5%89%82" class="mw-redirect mw-disambig" title="杀菌剂">杀菌剂</a>、<a href="/wiki/%E9%98%B2%E8%85%90%E5%89%82" title="防腐剂">防腐剂</a>以及药物（如<a href="/wiki/%E4%B9%99%E9%85%B0%E6%B0%B4%E6%9D%A8%E9%85%B8" title="乙酰水杨酸">阿司匹林</a>）的重要原料。 </p> <style data-mw-deduplicate="TemplateStyles:r56805754">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="发现"><span id=".E5.8F.91.E7.8E.B0"></span>发现</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=1" title="编辑章节：发现"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>苯酚是由<a href="/wiki/%E5%BE%B7%E5%9B%BD" title="德国">德国</a>化学家荣格（Runge F）于1834年在<a href="/wiki/%E7%85%A4%E7%84%A6%E6%B2%B9" title="煤焦油">煤焦油</a>中发现的，故又称石炭酸（Carbolic acid）。 </p> <div class="mw-heading mw-heading2"><h2 id="结构"><span id=".E7.BB.93.E6.9E.84"></span>结构</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=2" title="编辑章节：结构"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>苯酚分子由一个<a href="/wiki/%E7%BE%9F%E5%9F%BA" title="羟基">羟基</a>直接连在<a href="/wiki/%E8%8A%B3%E9%A6%99%E7%8E%AF" title="芳香环">苯环</a>上构成。根据<a href="/wiki/%E8%8B%AF" title="苯">苯</a>的凯库勒式，这个羟基是连在双键上的，为烯醇式结构。但由于苯环的稳定性，这样的结构几乎不会转化为酮式结构。 </p><p>苯酚具有以下<a href="/wiki/%E5%85%B1%E6%8C%AF%E7%BB%93%E6%9E%84" class="mw-redirect" title="共振结构">共振结构</a>： </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:PhenolResonance.svg" class="mw-file-description" title="苯酚的共振结构"><img alt="苯酚的共振结构" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/PhenolResonance.svg/300px-PhenolResonance.svg.png" decoding="async" width="300" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/PhenolResonance.svg/450px-PhenolResonance.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/PhenolResonance.svg/600px-PhenolResonance.svg.png 2x" data-file-width="439" data-file-height="88" /></a></span></dd></dl> <p>苯酚盐负离子则有以下共振结构： </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:PhenolateResonance.svg" class="mw-file-description" title="苯酚负离子的共振结构"><img alt="苯酚负离子的共振结构" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/PhenolateResonance.svg/300px-PhenolateResonance.svg.png" decoding="async" width="300" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/PhenolateResonance.svg/450px-PhenolateResonance.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/PhenolateResonance.svg/600px-PhenolateResonance.svg.png 2x" data-file-width="438" data-file-height="83" /></a></span></dd></dl> <p>酚羟基的氧原子采用sp<sup>2</sup>杂化，提供1对孤电子与苯环的6个碳原子共同形成<a href="/wiki/%E7%A6%BB%E5%9F%9F" class="mw-redirect" title="离域">离域</a><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle \ {\Pi }_{7}^{8}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mtext> </mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mi mathvariant="normal">Π</mi> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>7</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>8</mn> </mrow> </msubsup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \ {\Pi }_{7}^{8}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/4566e63bcdf85ea592451c65d60ebbc11fc86e52" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.838ex; width:3.378ex; height:3.176ex;" alt="{\displaystyle \ {\Pi }_{7}^{8}}"></span> 键。大Π键加强了烯醇的酸性，羟基的推电子效应又加强了O-H键的极性，因此苯酚中羟基的氢可以电离出来。 </p> <div class="mw-heading mw-heading2"><h2 id="物理性质"><span id=".E7.89.A9.E7.90.86.E6.80.A7.E8.B4.A8"></span>物理性质</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=3" title="编辑章节：物理性质"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>苯酚熔点为40.5℃，沸点为181.7℃，常温下为一种无色或白色的<a href="/wiki/%E6%99%B6%E4%BD%93" title="晶体">晶体</a>，有特殊气味。苯酚密度比水大，微溶于冷水，可在水中形成白色混浊；但易溶于65℃以上的热水。易溶于醇、醚等有机溶剂。常温时苯酚含水27％可成为均匀液体。 </p> <div class="mw-heading mw-heading2"><h2 id="化学性质"><span id=".E5.8C.96.E5.AD.A6.E6.80.A7.E8.B4.A8"></span>化学性质</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=4" title="编辑章节：化学性质"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dt>酸碱反应</dt></dl> <p>苯酚具有弱酸性，能与碱反应： </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\rm {PhOH+NaOH\rightarrow PhONa+H_{2}O\,}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mi mathvariant="normal">P</mi> <mi mathvariant="normal">h</mi> <mi mathvariant="normal">O</mi> <mi mathvariant="normal">H</mi> <mo>+</mo> <mi mathvariant="normal">N</mi> <mi mathvariant="normal">a</mi> <mi mathvariant="normal">O</mi> <mi mathvariant="normal">H</mi> <mo stretchy="false">→</mo> <mi mathvariant="normal">P</mi> <mi mathvariant="normal">h</mi> <mi mathvariant="normal">O</mi> <mi mathvariant="normal">N</mi> <mi mathvariant="normal">a</mi> <mo>+</mo> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> <mi mathvariant="normal">O</mi> <mspace width="thinmathspace" /> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\rm {PhOH+NaOH\rightarrow PhONa+H_{2}O\,}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/e8da90335ec685d5aac189bee0a31bdd03f1bc92" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.671ex; width:34.76ex; height:2.509ex;" alt="{\displaystyle {\rm {PhOH+NaOH\rightarrow PhONa+H_{2}O\,}}}"></span></dd></dl> <p>苯酚pKa=10，酸性介于碳酸两级电离之间，因此苯酚不能与<a href="/wiki/%E7%A2%B3%E9%85%B8%E6%B0%AB%E9%88%89" class="mw-redirect" title="碳酸氫鈉">碳酸氫鈉</a>等弱碱反应： </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\rm {\ PhO^{-}+CO_{2}+H_{2}O\rightarrow PhOH+HCO_{3}^{-}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext> </mtext> <mi mathvariant="normal">P</mi> <mi mathvariant="normal">h</mi> <msup> <mi mathvariant="normal">O</mi> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> <mo>+</mo> <mi mathvariant="normal">C</mi> <msub> <mi mathvariant="normal">O</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> <mo>+</mo> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> <mi mathvariant="normal">O</mi> <mo stretchy="false">→</mo> <mi mathvariant="normal">P</mi> <mi mathvariant="normal">h</mi> <mi mathvariant="normal">O</mi> <mi mathvariant="normal">H</mi> <mo>+</mo> <mi mathvariant="normal">H</mi> <mi mathvariant="normal">C</mi> <msubsup> <mi mathvariant="normal">O</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msubsup> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\rm {\ PhO^{-}+CO_{2}+H_{2}O\rightarrow PhOH+HCO_{3}^{-}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/14af84164242d5371907bdee8181f858851d5367" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:41.223ex; height:3.176ex;" alt="{\displaystyle {\rm {\ PhO^{-}+CO_{2}+H_{2}O\rightarrow PhOH+HCO_{3}^{-}}}}"></span></dd></dl> <p>此反应现象：二氧化碳通入后，溶液中出现白色混浊。 </p> <dl><dt>显色反应</dt></dl> <p>苯酚遇<a href="/wiki/%E4%B8%89%E6%B0%AF%E5%8C%96%E9%93%81" class="mw-redirect" title="三氯化铁">三氯化铁</a>溶液显紫色，原因是苯酚根离子与Fe<sup>3+</sup>形成了有颜色的<a href="/wiki/%E9%85%8D%E5%90%88%E7%89%A9" title="配合物">配合物</a>。 </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\rm {\ 6PhOH+FeCl_{3}\rightarrow H_{3}[Fe(OPh)_{6}]}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext> </mtext> <mn>6</mn> <mi mathvariant="normal">P</mi> <mi mathvariant="normal">h</mi> <mi mathvariant="normal">O</mi> <mi mathvariant="normal">H</mi> <mo>+</mo> <mi mathvariant="normal">F</mi> <mi mathvariant="normal">e</mi> <mi mathvariant="normal">C</mi> <msub> <mi mathvariant="normal">l</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msub> <mo stretchy="false">→</mo> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msub> <mo stretchy="false">[</mo> <mi mathvariant="normal">F</mi> <mi mathvariant="normal">e</mi> <mo stretchy="false">(</mo> <mi mathvariant="normal">O</mi> <mi mathvariant="normal">P</mi> <mi mathvariant="normal">h</mi> <msub> <mo stretchy="false">)</mo> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> </msub> <mo stretchy="false">]</mo> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\rm {\ 6PhOH+FeCl_{3}\rightarrow H_{3}[Fe(OPh)_{6}]}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/046c2cd1dfbf511b14ae46217344394c8b98d953" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.838ex; width:34.742ex; height:2.843ex;" alt="{\displaystyle {\rm {\ 6PhOH+FeCl_{3}\rightarrow H_{3}[Fe(OPh)_{6}]}}}"></span>(紫色) <span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\rm {\ +3HCl}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext> </mtext> <mo>+</mo> <mn>3</mn> <mi mathvariant="normal">H</mi> <mi mathvariant="normal">C</mi> <mi mathvariant="normal">l</mi> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\rm {\ +3HCl}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/78bb5e1fdd87b2159251480b1fce3c361f432ee3" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:8.652ex; height:2.343ex;" alt="{\displaystyle {\rm {\ +3HCl}}}"></span></dd></dl> <dl><dt>取代反应</dt></dl> <ul><li>苯环上的亲电取代：苯酚由于结构中有苯环，可以在环上发生类似苯的<a href="/wiki/%E4%BA%B2%E7%94%B5%E5%8F%96%E4%BB%A3%E5%8F%8D%E5%BA%94" title="亲电取代反应">亲电取代反应</a>，如<a href="/wiki/%E7%A1%9D%E5%8C%96" class="mw-redirect" title="硝化">硝化</a>、<a href="/wiki/%E9%B9%B5%E5%8C%96" title="鹵化">卤代</a>等：</li></ul> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:PhenolNitration.svg" class="mw-file-description" title="苯酚的硝化反应"><img alt="苯酚的硝化反应" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/PhenolNitration.svg/420px-PhenolNitration.svg.png" decoding="async" width="420" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/PhenolNitration.svg/630px-PhenolNitration.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/15/PhenolNitration.svg/840px-PhenolNitration.svg.png 2x" data-file-width="304" data-file-height="89" /></a><figcaption>苯酚的硝化反应</figcaption></figure> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:PhenolBromination.svg" class="mw-file-description" title="苯酚的溴化反应"><img alt="苯酚的溴化反应" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/PhenolBromination.svg/700px-PhenolBromination.svg.png" decoding="async" width="700" height="355" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/PhenolBromination.svg/1050px-PhenolBromination.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/PhenolBromination.svg/1400px-PhenolBromination.svg.png 2x" data-file-width="521" data-file-height="264" /></a><figcaption>苯酚的溴化反应</figcaption></figure> <p>对比<a href="/wiki/%E8%8B%AF#取代反应" title="苯">苯的相应反应</a>可以发现，苯酚环上的取代比苯容易得多。这是因为羟基有<a href="/w/index.php?title=%E7%BB%99%E7%94%B5%E5%AD%90%E6%95%88%E5%BA%94&action=edit&redlink=1" class="new" title="给电子效应（页面不存在）">给电子效应</a>，使苯环电子云密度增加。 </p><p>值得注意的是，苯酚的亲电取代总是发生在羟基的<b>邻位</b>和<b>对位</b>。这是羟基等给电子基团的共性。 </p> <ul><li>酚羟基上的取代：酚羟基上的氢原子可以被含碳基团取代，生成<a href="/wiki/%E9%86%9A" title="醚">醚</a>或<a href="/wiki/%E9%85%AF" title="酯">酯</a>。</li></ul> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:PhenolAlkylation.svg" class="mw-file-description" title="苯酚被溴乙烷乙基化为苯乙醚"><img alt="苯酚被溴乙烷乙基化为苯乙醚" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/PhenolAlkylation.svg/430px-PhenolAlkylation.svg.png" decoding="async" width="430" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/PhenolAlkylation.svg/645px-PhenolAlkylation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/PhenolAlkylation.svg/860px-PhenolAlkylation.svg.png 2x" data-file-width="334" data-file-height="78" /></a><figcaption>苯酚被溴乙烷乙基化为苯乙醚</figcaption></figure> <dl><dt>氧化还原反应</dt></dl><p> 苯酚在空气中久置会变为粉红色，是因为生成了<a href="/wiki/%E8%8B%AF%E9%86%8C" title="苯醌">苯醌</a>：</p><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:PhenolOxidation.svg" class="mw-file-description" title="苯酚被氧气氧化为苯醌。"><img alt="苯酚被氧气氧化为苯醌。" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/PhenolOxidation.svg/300px-PhenolOxidation.svg.png" decoding="async" width="300" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/PhenolOxidation.svg/450px-PhenolOxidation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/PhenolOxidation.svg/600px-PhenolOxidation.svg.png 2x" data-file-width="219" data-file-height="98" /></a><figcaption>苯酚被氧气氧化为苯醌。</figcaption></figure> <p>苯酚的氧化产物一般是<a href="/wiki/%E5%AF%B9%E8%8B%AF%E9%86%8C" class="mw-redirect" title="对苯醌">对苯醌</a>。这个反应也可以用<a href="/wiki/%E6%BA%B4" title="溴">溴</a>作氧化剂。 </p> <dl><dt>缩合反应</dt></dl> <p>苯酚与甲醛在酸或碱的催化下发生缩合，生成<a href="/wiki/%E9%85%9A%E9%86%9B%E6%A0%91%E8%84%82" title="酚醛树脂">酚醛树脂</a>。 </p> <div class="mw-heading mw-heading2"><h2 id="制备"><span id=".E5.88.B6.E5.A4.87"></span>制备</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=5" title="编辑章节：制备"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dt>熔融苯磺酸法</dt></dl> <p>苯酚可由<a href="/wiki/%E8%8B%AF%E7%A3%BA%E9%85%B8" title="苯磺酸">苯磺酸</a>与<a href="/wiki/%E7%A2%B1" title="碱">碱</a>熔融反应制得： </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle \mathrm {C_{6}H_{5}SO_{3}Na\ +\ 2NaOH\longrightarrow \ C_{6}H_{5}ONa\ +\ Na_{2}SO_{3}\ +\ H_{2}O} }"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msub> <mi mathvariant="normal">C</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> </msub> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> </msub> <mi mathvariant="normal">S</mi> <msub> <mi mathvariant="normal">O</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msub> <mi mathvariant="normal">N</mi> <mi mathvariant="normal">a</mi> <mtext> </mtext> <mo>+</mo> <mtext> </mtext> <mn>2</mn> <mi mathvariant="normal">N</mi> <mi mathvariant="normal">a</mi> <mi mathvariant="normal">O</mi> <mi mathvariant="normal">H</mi> <mo stretchy="false">⟶</mo> <mtext> </mtext> <msub> <mi mathvariant="normal">C</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> </msub> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> </msub> <mi mathvariant="normal">O</mi> <mi mathvariant="normal">N</mi> <mi mathvariant="normal">a</mi> <mtext> </mtext> <mo>+</mo> <mtext> </mtext> <mi mathvariant="normal">N</mi> <msub> <mi mathvariant="normal">a</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> <mi mathvariant="normal">S</mi> <msub> <mi mathvariant="normal">O</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msub> <mtext> </mtext> <mo>+</mo> <mtext> </mtext> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> <mi mathvariant="normal">O</mi> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \mathrm {C_{6}H_{5}SO_{3}Na\ +\ 2NaOH\longrightarrow \ C_{6}H_{5}ONa\ +\ Na_{2}SO_{3}\ +\ H_{2}O} }</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/0c4bb0d36c0936b557d2034d34fb50317a2f713b" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.671ex; width:60.854ex; height:2.509ex;" alt="{\displaystyle \mathrm {C_{6}H_{5}SO_{3}Na\ +\ 2NaOH\longrightarrow \ C_{6}H_{5}ONa\ +\ Na_{2}SO_{3}\ +\ H_{2}O} }"></span></dd></dl> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:PhenolSynthesisFromBenzenesulfonicAcid.svg" class="mw-file-description" title="由苯磺酸的碱熔制取苯酚"><img alt="由苯磺酸的碱熔制取苯酚" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/PhenolSynthesisFromBenzenesulfonicAcid.svg/650px-PhenolSynthesisFromBenzenesulfonicAcid.svg.png" decoding="async" width="650" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/PhenolSynthesisFromBenzenesulfonicAcid.svg/975px-PhenolSynthesisFromBenzenesulfonicAcid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/72/PhenolSynthesisFromBenzenesulfonicAcid.svg/1300px-PhenolSynthesisFromBenzenesulfonicAcid.svg.png 2x" data-file-width="436" data-file-height="54" /></a><figcaption>由苯磺酸的碱熔制取苯酚</figcaption></figure> <p>用酸处理即得苯酚。此法是最早用来制取苯酚的方法，<a href="/wiki/%E8%90%98%E9%85%9A" title="萘酚">萘酚</a>也用类似的方法制取。 </p> <dl><dt><a href="/wiki/%E5%BC%82%E4%B8%99%E8%8B%AF%E6%B3%95" class="mw-redirect" title="异丙苯法">异丙苯法</a></dt></dl> <p>此法初始原料为苯，通过<a href="/wiki/%E5%82%85-%E5%85%8B%E5%8F%8D%E5%BA%94" class="mw-redirect" title="傅-克反应">傅-克反应</a>与<a href="/wiki/%E4%B8%99%E7%83%AF" title="丙烯">丙烯</a>加成为<a href="/wiki/%E5%BC%82%E4%B8%99%E8%8B%AF" title="异丙苯">异丙苯</a>，再由异丙苯氧化为苯酚。此法同时生成<a href="/wiki/%E4%B8%99%E9%85%AE" title="丙酮">丙酮</a>。 </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\rm {\ C_{6}H_{6}+H_{2}C\!=\!CHCH_{3}\rightarrow C_{6}H_{5}CH(CH_{3})_{2}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext> </mtext> <msub> <mi mathvariant="normal">C</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> </msub> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> </msub> <mo>+</mo> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> <mi mathvariant="normal">C</mi> <mspace width="negativethinmathspace" /> <mo>=</mo> <mspace width="negativethinmathspace" /> <mi mathvariant="normal">C</mi> <mi mathvariant="normal">H</mi> <mi mathvariant="normal">C</mi> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msub> <mo stretchy="false">→</mo> <msub> <mi mathvariant="normal">C</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> </msub> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> </msub> <mi mathvariant="normal">C</mi> <mi mathvariant="normal">H</mi> <mo stretchy="false">(</mo> <mi mathvariant="normal">C</mi> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msub> <msub> <mo stretchy="false">)</mo> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\rm {\ C_{6}H_{6}+H_{2}C\!=\!CHCH_{3}\rightarrow C_{6}H_{5}CH(CH_{3})_{2}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/7c518d2c827540c759afca2daf73bef2713006da" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.838ex; width:43.551ex; height:2.843ex;" alt="{\displaystyle {\rm {\ C_{6}H_{6}+H_{2}C\!=\!CHCH_{3}\rightarrow C_{6}H_{5}CH(CH_{3})_{2}}}}"></span></dd> <dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\rm {\ C_{6}H_{5}CH(CH_{3})_{2}+O_{2}\rightarrow C_{6}H_{5}OH+CH_{3}COCH_{3}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext> </mtext> <msub> <mi mathvariant="normal">C</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> </msub> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> </msub> <mi mathvariant="normal">C</mi> <mi mathvariant="normal">H</mi> <mo stretchy="false">(</mo> <mi mathvariant="normal">C</mi> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msub> <msub> <mo stretchy="false">)</mo> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> <mo>+</mo> <msub> <mi mathvariant="normal">O</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> </msub> <mo stretchy="false">→</mo> <msub> <mi mathvariant="normal">C</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> </msub> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> </msub> <mi mathvariant="normal">O</mi> <mi mathvariant="normal">H</mi> <mo>+</mo> <mi mathvariant="normal">C</mi> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msub> <mi mathvariant="normal">C</mi> <mi mathvariant="normal">O</mi> <mi mathvariant="normal">C</mi> <msub> <mi mathvariant="normal">H</mi> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msub> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\rm {\ C_{6}H_{5}CH(CH_{3})_{2}+O_{2}\rightarrow C_{6}H_{5}OH+CH_{3}COCH_{3}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/bff3a5e03cb31bede37b28670eadface812003e1" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.838ex; width:50.546ex; height:2.843ex;" alt="{\displaystyle {\rm {\ C_{6}H_{5}CH(CH_{3})_{2}+O_{2}\rightarrow C_{6}H_{5}OH+CH_{3}COCH_{3}}}}"></span></dd></dl> <p>第二步反应是一个<a href="/wiki/%E8%87%AA%E7%94%B1%E5%9F%BA%E5%8F%8D%E6%87%89" class="mw-redirect" title="自由基反應">自由基反应</a>。 </p> <dl><dt>氯苯水解</dt></dl> <p>通过<a href="/wiki/%E6%B0%AF%E8%8B%AF" title="氯苯">氯苯</a>在<a href="/wiki/%E6%B0%A2%E6%B0%A7%E5%8C%96%E9%92%A0" title="氢氧化钠">氢氧化钠</a>水溶液中的水解，也可以制得苯酚。由于氯苯的氯原子参与<a href="/wiki/%E8%8A%B3%E9%A6%99%E7%8E%AF" title="芳香环">苯环</a>的共轭，这个水解过程十分困难，需要在高压（28MPa）、高温（300℃）、以<a href="/wiki/%E9%93%9C" title="铜">铜</a>作<a href="/wiki/%E5%82%AC%E5%8C%96%E5%89%82" title="催化剂">催化剂</a>的条件下进行。 </p> <dl><dt>其他方法</dt></dl><p> 苯酚也可由<a href="/wiki/%E8%8B%AF%E8%83%BA" title="苯胺">苯胺</a>经<a href="/wiki/%E9%87%8D%E6%B0%AE%E7%9B%90" title="重氮盐">重氮盐</a>水解制得。</p><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:PhenolSynthesisFromAniline.svg" class="mw-file-description" title="由苯胺制取苯酚"><img alt="由苯胺制取苯酚" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/PhenolSynthesisFromAniline.svg/680px-PhenolSynthesisFromAniline.svg.png" decoding="async" width="680" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/PhenolSynthesisFromAniline.svg/1020px-PhenolSynthesisFromAniline.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/PhenolSynthesisFromAniline.svg/1360px-PhenolSynthesisFromAniline.svg.png 2x" data-file-width="479" data-file-height="64" /></a><figcaption>由苯胺制取苯酚</figcaption></figure><p> 2007年<a href="/wiki/%E5%90%89%E6%9E%97%E5%A4%A7%E5%AD%A6" title="吉林大学">吉林大学</a>化学学院的冯守华等人在<a href="/wiki/%E6%9C%89%E6%9C%BA%E5%8C%96%E5%AD%A6%E9%80%9A%E8%AE%AF" title="有机化学通讯">有机化学通讯</a>期刊上发表文章称，他们用<a href="/wiki/%E7%A2%B3%E9%85%B8%E6%B0%A2%E9%92%A0" title="碳酸氢钠">碳酸氢钠</a>和<a href="/w/index.php?title=%E9%93%81%E7%B2%89&action=edit&redlink=1" class="new" title="铁粉（页面不存在）">铁粉</a>在仿早期地球环境的条件下进行<a href="/wiki/%E6%B0%B4%E7%83%AD%E5%90%88%E6%88%90%E6%B3%95" title="水热合成法">水热合成</a>（水，200℃，1.9GPa），在产物中得到了产率为0.8%的苯酚。<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></p><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:PhenolSynthesis.svg" class="mw-file-description" title="苯酚制取 2007年"><img alt="苯酚制取 2007年" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/PhenolSynthesis.svg/400px-PhenolSynthesis.svg.png" decoding="async" width="400" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/PhenolSynthesis.svg/600px-PhenolSynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/PhenolSynthesis.svg/800px-PhenolSynthesis.svg.png 2x" data-file-width="268" data-file-height="73" /></a><figcaption>苯酚制取 2007年</figcaption></figure><p> 他们认为反应机理如下：<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></p><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:PhenolProposedMechanism.svg" class="mw-file-description" title="苯酚制取机理"><img alt="苯酚制取机理" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/PhenolProposedMechanism.svg/800px-PhenolProposedMechanism.svg.png" decoding="async" width="800" height="1166" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/PhenolProposedMechanism.svg/1200px-PhenolProposedMechanism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/81/PhenolProposedMechanism.svg/1600px-PhenolProposedMechanism.svg.png 2x" data-file-width="558" data-file-height="813" /></a><figcaption>苯酚制取机理</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="安全"><span id=".E5.AE.89.E5.85.A8"></span>安全</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=6" title="编辑章节：安全"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>苯酚有毒。苯酚及其浓溶液对皮肤有强烈的刺激作用，若不慎将苯酚沾到皮肤上，应用<a href="/wiki/%E9%85%92%E7%B2%BE" class="mw-redirect" title="酒精">酒精</a>或<a href="/wiki/%E8%81%9A%E4%B9%99%E4%BA%8C%E9%86%87" title="聚乙二醇">聚乙二醇</a>清洗；若量较大或者混有<a href="/wiki/%E6%B0%AF%E4%BB%BF" title="氯仿">氯仿</a>，则需要进行急救。沾到衣服上也需用大量水冲洗。 </p> <div class="mw-heading mw-heading2"><h2 id="工业及醫學用途"><span id=".E5.B7.A5.E4.B8.9A.E5.8F.8A.E9.86.AB.E5.AD.B8.E7.94.A8.E9.80.94"></span>工业及醫學用途</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=7" title="编辑章节：工业及醫學用途"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>苯酚可作杀菌剂、麻醉剂、防腐剂。英國外科醫生<a href="/wiki/%E7%BA%A6%E7%91%9F%E5%A4%AB%C2%B7%E6%9D%8E%E6%96%AF%E7%89%B9" title="约瑟夫·李斯特">约瑟夫·李斯特</a>（Lister J）於1865年将其用于外科手术消毒，為最早以藥劑進行術前消毒的醫生；但由于苯酚的毒性，这一技术最终被取代。现在苯酚可用于制备消毒剂，如TCP；或用其稀溶液直接进行消毒。 </p><p>苯酚是多种化工产品的原料，用来合成阿司匹林等药品，以及一些农药、香料、染料。亦用来合成树脂，最主要的一种是和甲醛缩合而成的<a href="/wiki/%E9%85%9A%E9%86%9B%E6%A0%91%E8%84%82" title="酚醛树脂">酚醛树脂</a>。 </p><p>尽管苯酚的浓溶液毒性很强，它仍在整形外科手术中充当脱皮剂。 </p> <div class="mw-heading mw-heading2"><h2 id="衍生物"><span id=".E8.A1.8D.E7.94.9F.E7.89.A9"></span>衍生物</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=8" title="编辑章节：衍生物"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/%E8%8B%AF%E4%BA%8C%E9%85%9A" title="苯二酚">苯二酚</a>、<a href="/wiki/%E8%8B%AF%E4%B8%89%E9%85%9A" title="苯三酚">苯三酚</a></li> <li><a href="/wiki/%E7%A1%9D%E5%9F%BA%E8%8B%AF%E9%85%9A" title="硝基苯酚">硝基苯酚</a>、<a href="/wiki/%E4%B8%89%E7%A1%9D%E5%9F%BA%E8%8B%AF%E9%85%9A" class="mw-redirect" title="三硝基苯酚">三硝基苯酚</a>、<a href="/wiki/%E4%B8%89%E6%BA%B4%E8%8B%AF%E9%85%9A" title="三溴苯酚">三溴苯酚</a>、<a href="/wiki/%E4%BA%94%E6%B0%AF%E8%8B%AF%E9%85%9A" class="mw-redirect" title="五氯苯酚">五氯苯酚</a></li> <li><a href="/wiki/%E8%8B%AF%E9%86%8C" title="苯醌">苯醌</a>：<a href="/wiki/%E5%AF%B9%E8%8B%AF%E9%86%8C" class="mw-redirect" title="对苯醌">对苯醌</a>、<a href="/wiki/%E9%82%BB%E8%8B%AF%E9%86%8C" class="mw-redirect" title="邻苯醌">邻苯醌</a></li> <li><a href="/wiki/%E7%94%B2%E9%85%9A" title="甲酚">甲酚</a>、<a href="/wiki/%E7%99%BE%E9%87%8C%E9%85%9A" title="百里酚">百里酚</a></li> <li><a href="/wiki/%E6%B0%B4%E6%9D%A8%E9%85%B8" class="mw-redirect" title="水杨酸">水杨酸</a>、<a href="/wiki/%E4%B9%99%E9%85%B0%E6%B0%B4%E6%9D%A8%E9%85%B8" title="乙酰水杨酸">乙酰水杨酸</a></li> <li><a href="/wiki/%E8%90%98%E9%85%9A" title="萘酚">萘酚</a>、<a href="/w/index.php?title=%E8%92%BD%E9%85%9A&action=edit&redlink=1" class="new" title="蒽酚（页面不存在）">蒽酚</a></li> <li><a href="/wiki/%E9%85%9A%E9%85%9E" title="酚酞">酚酞</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="参见"><span id=".E5.8F.82.E8.A7.81"></span>参见</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=9" title="编辑章节：参见"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/%E9%85%9A" title="酚">酚</a></li> <li><a href="/wiki/%E8%8B%AF" title="苯">苯</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="註釋"><span id=".E8.A8.BB.E9.87.8B"></span>註釋</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=10" title="编辑章节：註釋"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="reflist" style="list-style-type: decimal;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><cite class="citation journal">Tian, Ge; Yuan, Hongming; Mu, Ying; He, Chao; Feng, Shouhua. <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/10.1021/ol070597o">Hydrothermal Reactions from Sodium Hydrogen Carbonate to Phenol</a>. <a href="/wiki/%E6%9C%89%E6%9C%BA%E5%8C%96%E5%AD%A6%E9%80%9A%E8%AE%AF" title="有机化学通讯">Organic Letters</a>. 2007-05, <b>9</b> (10): 2019–2021 <span class="reference-accessdate"> [<span class="nowrap">2020-11-05</span>]</span>. <a rel="nofollow" class="external text" href="//www.worldcat.org/issn/1523-7060"><span title="国际标准连续出版物号">ISSN 1523-7060</span></a>. <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fol070597o"><span title="數位物件識別號">doi:10.1021/ol070597o</span></a>. （原始内容<a rel="nofollow" class="external text" href="https://web.archive.org/web/20191202001206/https://pubs.acs.org/doi/10.1021/ol070597o">存档</a>于2019-12-02） <span style="font-family: sans-serif; cursor: default; color:var(--color-subtle, #54595d); font-size: 0.8em; bottom: 0.1em; font-weight: bold;" title="连接到英语网页">（英语）</span>.</cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E8%8B%AF%E9%85%9A&rft.atitle=Hydrothermal+Reactions+from+Sodium+Hydrogen+Carbonate+to+Phenol&rft.au=Feng%2C+Shouhua&rft.au=He%2C+Chao&rft.au=Mu%2C+Ying&rft.au=Yuan%2C+Hongming&rft.aufirst=Ge&rft.aulast=Tian&rft.date=2007-05&rft.genre=article&rft.issn=1523-7060&rft.issue=10&rft.jtitle=Organic+Letters&rft.pages=2019-2021&rft.volume=9&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2F10.1021%2Fol070597o&rft_id=info%3Adoi%2F10.1021%2Fol070597o&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><cite class="citation web">Shouhua Feng, Ge Tian, Hongming Yuan, Ying Mu & Chao He. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20071215143503/http://canli.dicp.ac.cn/Gruop%20Seminars%20Pdf/20070630dewang%20si.pdf">Supporting Information for Hydrothermal Reactions from Sodium Hydrogen Carbonate to Phenol</a> <span style="font-size:85%;">(PDF)</span>. <span class="reference-accessdate"> [<span class="nowrap">2009-08-15</span>]</span>. （<a rel="nofollow" class="external text" href="http://www.canli.dicp.ac.cn/Gruop%20Seminars%20Pdf/20070630dewang%20si.pdf">原始内容</a> <span style="font-size:85%;">(PDF)</span>存档于2007-12-15）.</cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E8%8B%AF%E9%85%9A&rft.au=Shouhua+Feng%2C+Ge+Tian%2C+Hongming+Yuan%2C+Ying+Mu+%26+Chao+He&rft.btitle=Supporting+Information+for+Hydrothermal+Reactions+from+Sodium+Hydrogen+Carbonate+to+Phenol&rft.genre=unknown&rft_id=http%3A%2F%2Fwww.canli.dicp.ac.cn%2FGruop%2520Seminars%2520Pdf%2F20070630dewang%2520si.pdf&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook" class="Z3988"><span style="display:none;"> </span></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="参考文献"><span id=".E5.8F.82.E8.80.83.E6.96.87.E7.8C.AE"></span>参考文献</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%8B%AF%E9%85%9A&action=edit&section=11" title="编辑章节：参考文献"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r80540462">.mw-parser-output .refbegin{font-size:90%;margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .refbegin-100{font-size:100%}</style><div class="refbegin" style=""> <ul><li><cite class="citation book">邢其毅. 第十七章. <a rel="nofollow" class="external text" href="https://www.worldcat.org/title/ji-chu-you-ji-hua-xue/oclc/768503522">基础有机化学</a>. 北京: 高等教育出版社. 1993 <span class="reference-accessdate"> [<span class="nowrap">2020-11-05</span>]</span>. <a href="/wiki/Special:%E7%BD%91%E7%BB%9C%E4%B9%A6%E6%BA%90/978-7-04-004276-4" title="Special:网络书源/978-7-04-004276-4"><span title="国际标准书号">ISBN</span> 978-7-04-004276-4</a>. <a rel="nofollow" class="external text" href="//www.worldcat.org/oclc/768503522"><span title="OCLC">OCLC 768503522</span></a>. （原始内容<a rel="nofollow" class="external text" href="https://web.archive.org/web/20201218084537/https://www.worldcat.org/title/ji-chu-you-ji-hua-xue/oclc/768503522">存档</a>于2020-12-18） <span style="font-family: sans-serif; cursor: default; color:var(--color-subtle, #54595d); font-size: 0.8em; bottom: 0.1em; font-weight: bold;" title="连接到中文网页">（中文）</span>.</cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E8%8B%AF%E9%85%9A&rft.atitle=%E7%AC%AC%E5%8D%81%E4%B8%83%E7%AB%A0&rft.au=%E9%82%A2%E5%85%B6%E6%AF%85&rft.btitle=%E5%9F%BA%E7%A1%80%E6%9C%89%E6%9C%BA%E5%8C%96%E5%AD%A6&rft.date=1993&rft.genre=bookitem&rft.isbn=978-7-04-004276-4&rft.place=%E5%8C%97%E4%BA%AC&rft.pub=%E9%AB%98%E7%AD%89%E6%95%99%E8%82%B2%E5%87%BA%E7%89%88%E7%A4%BE&rft_id=https%3A%2F%2Fwww.worldcat.org%2Ftitle%2Fji-chu-you-ji-hua-xue%2Foclc%2F768503522&rft_id=info%3Aoclcnum%2F768503522&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook" class="Z3988"><span style="display:none;"> </span></span></li></ul> </div> <div style="clear: both; height: 1em"></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r84265675">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:%E8%8A%B3%E9%A6%99%E6%97%8F%E5%8C%96%E5%90%88%E7%89%A9" title="Template:芳香族化合物"><abbr title="查看该模板">查</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:%E8%8A%B3%E9%A6%99%E6%97%8F%E5%8C%96%E5%90%88%E7%89%A9" title="Template talk:芳香族化合物"><abbr title="讨论该模板">论</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:%E7%BC%96%E8%BE%91%E9%A1%B5%E9%9D%A2/Template:%E8%8A%B3%E9%A6%99%E6%97%8F%E5%8C%96%E5%90%88%E7%89%A9" title="Special:编辑页面/Template:芳香族化合物"><abbr title="编辑该模板">编</abbr></a></li></ul></div><div id="芳香族化合物" style="font-size:110%;margin:0 5em"><a href="/wiki/%E8%8A%B3%E9%A6%99%E6%80%A7" title="芳香性">芳香族化合物</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">单取代苯<br />（简单）</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E7%94%B2%E8%8B%AF" title="甲苯">甲苯</a></li> <li><a href="/wiki/%E4%B9%99%E8%8B%AF" title="乙苯">乙苯</a></li> <li><a href="/wiki/%E6%AD%A3%E4%B8%99%E8%8B%AF" title="正丙苯">正丙苯</a></li> <li><a href="/wiki/%E5%BC%82%E4%B8%99%E8%8B%AF" title="异丙苯">异丙苯</a></li> <li><a href="/wiki/%E8%8B%AF%E4%B9%99%E7%83%AF" title="苯乙烯">苯乙烯</a></li> <li><a class="mw-selflink selflink">苯酚</a></li> <li><a href="/wiki/%E8%8B%AF%E4%B9%99%E9%85%AE" title="苯乙酮">苯乙酮</a></li> <li><a href="/wiki/%E8%8B%AF%E7%94%B2%E9%86%9A" title="苯甲醚">苯甲醚</a></li> <li><a href="/wiki/%E8%8B%AF%E4%B9%99%E9%86%9A" title="苯乙醚">苯乙醚</a></li> <li><a href="/wiki/%E8%8B%AF%E7%94%B2%E9%86%87" title="苯甲醇">苯甲醇</a></li> <li><a href="/wiki/%E8%8B%AF%E7%94%B2%E9%86%9B" title="苯甲醛">苯甲醛</a></li> <li><a href="/wiki/%E8%8B%AF%E7%94%B2%E9%85%B0%E6%B0%AF" title="苯甲酰氯">苯甲酰氯</a></li> <li><a href="/wiki/%E8%8B%AF%E7%94%B2%E9%85%B8" title="苯甲酸">苯甲酸</a></li> <li><a href="/wiki/%E8%8B%AF%E7%94%B2%E8%85%88" title="苯甲腈">苯甲腈</a></li> <li><a href="/wiki/%E7%A1%9D%E5%9F%BA%E8%8B%AF" title="硝基苯">硝基苯</a></li> <li><a href="/wiki/%E4%BA%9A%E7%A1%9D%E5%9F%BA%E8%8B%AF" title="亚硝基苯">亚硝基苯</a></li> <li><a href="/wiki/%E8%8B%AF%E8%83%BA" title="苯胺">苯胺</a></li> <li><a href="/wiki/%E8%8B%AF%E8%83%B2" title="苯胲">苯胲</a></li> <li><a href="/wiki/%E7%96%8A%E6%B0%AE%E8%8B%AF" title="疊氮苯">疊氮苯</a></li> <li><a href="/wiki/%E6%B0%9F%E8%8B%AF" title="氟苯">氟苯</a></li> <li><a href="/wiki/%E6%B0%AF%E8%8B%AF" title="氯苯">氯苯</a></li> <li><a href="/wiki/%E6%BA%B4%E8%8B%AF" title="溴苯">溴苯</a></li> <li><a href="/wiki/%E7%A2%98%E8%8B%AF" title="碘苯">碘苯</a></li> <li><a href="/wiki/%E4%BA%9E%E7%A2%98%E9%86%AF%E8%8B%AF" title="亞碘醯苯">亞碘醯苯</a></li> <li><a href="/wiki/%E8%8B%AF%E7%A3%BA%E9%85%B8" title="苯磺酸">苯磺酸</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">单取代苯<br />（其它）</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E4%BA%8C%E8%8B%AF%E5%9F%BA%E7%94%B2%E9%85%AE" title="二苯基甲酮">二苯基甲酮</a></li> <li><a href="/wiki/%E4%BA%8C%E8%8B%AF%E5%9F%BA%E4%B9%99%E4%BA%8C%E9%85%AE" title="二苯基乙二酮">二苯基乙二酮</a></li> <li><a href="/wiki/%E8%8B%AF%E4%B9%99%E9%85%B8" title="苯乙酸">苯乙酸</a></li> <li><a href="/wiki/%E6%89%81%E6%A1%83%E9%85%B8" title="扁桃酸">扁桃酸</a></li> <li><a href="/wiki/%E8%8B%AF%E4%B8%99%E9%85%B8" title="苯丙酸">苯丙酸</a></li> <li><a href="/wiki/%E8%82%89%E6%A1%82%E9%85%B8" title="肉桂酸">肉桂酸</a></li> <li><a href="/wiki/%E4%B9%99%E9%86%AF%E8%8B%AF%E8%83%BA" title="乙醯苯胺">乙酰苯胺</a></li> <li><a href="/wiki/%E8%8B%AF%E4%B9%99%E8%83%BA" title="苯乙胺">苯乙胺</a></li> <li><a href="/wiki/%E5%81%B6%E6%B0%AE%E8%8B%AF" title="偶氮苯">偶氮苯</a></li> <li><a href="/wiki/%E8%8B%AF%E5%9F%BA%E9%87%8D%E6%B0%AE%E9%B9%BD#氯化重氮苯" title="苯基重氮鹽">氯化重氮苯</a></li> <li><a href="/wiki/%E8%BF%87%E6%B0%A7%E5%8C%96%E8%8B%AF%E7%94%B2%E9%85%B0" title="过氧化苯甲酰">过氧化苯甲酰</a></li> <li><a href="/wiki/%E6%B0%AF%E5%8C%96%E8%8B%84" title="氯化苄">氯化苄</a></li> <li><a href="/wiki/%E8%8B%AF%E7%A3%BA%E9%85%B0%E6%B0%AF" title="苯磺酰氯">苯磺酰氯</a></li></ul> <ul><li><a href="/wiki/%E4%BA%8C%E8%8B%AF%E7%94%B2%E7%83%B7" title="二苯甲烷">二苯甲烷</a></li> <li><a href="/wiki/%E4%B8%89%E8%8B%AF%E7%94%B2%E7%83%B7" title="三苯甲烷">三苯甲烷</a></li> <li><a href="/wiki/%E4%B8%89%E8%8B%AF%E7%94%B2%E9%86%87" title="三苯甲醇">三苯甲醇</a></li> <li><a href="/wiki/%E4%B8%89%E8%8B%AF%E6%B0%AF%E7%94%B2%E7%83%B7" title="三苯氯甲烷">三苯氯甲烷</a></li> <li><a href="/wiki/%E5%9B%9B%E8%8B%AF%E7%94%B2%E7%83%B7" title="四苯甲烷">四苯甲烷</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">二取代苯</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E4%BA%8C%E7%94%B2%E8%8B%AF" title="二甲苯">二甲苯</a> <ul><li><a href="/wiki/%E9%82%BB%E4%BA%8C%E7%94%B2%E8%8B%AF" title="邻二甲苯">邻二甲苯</a></li> <li><a href="/wiki/%E9%97%B4%E4%BA%8C%E7%94%B2%E8%8B%AF" title="间二甲苯">间二甲苯</a></li> <li><a href="/wiki/%E5%AF%B9%E4%BA%8C%E7%94%B2%E8%8B%AF" title="对二甲苯">对二甲苯</a></li></ul></li> <li><a href="/wiki/%E8%8B%AF%E4%BA%8C%E9%85%9A" title="苯二酚">苯二酚</a> <ul><li><a href="/wiki/%E9%82%BB%E8%8B%AF%E4%BA%8C%E9%85%9A" title="邻苯二酚">邻苯二酚</a></li> <li><a href="/wiki/%E9%97%B4%E8%8B%AF%E4%BA%8C%E9%85%9A" title="间苯二酚">间苯二酚</a></li> <li><a href="/wiki/%E5%AF%B9%E8%8B%AF%E4%BA%8C%E9%85%9A" title="对苯二酚">对苯二酚</a></li></ul></li> <li><a href="/wiki/%E8%8B%AF%E4%BA%8C%E7%94%B2%E9%85%B8" title="苯二甲酸">苯二甲酸</a> <ul><li><a href="/wiki/%E9%82%BB%E8%8B%AF%E4%BA%8C%E7%94%B2%E9%85%B8" title="邻苯二甲酸">邻苯二甲酸</a></li> <li><a href="/wiki/%E9%97%B4%E8%8B%AF%E4%BA%8C%E7%94%B2%E9%85%B8" title="间苯二甲酸">间苯二甲酸</a></li> <li><a href="/wiki/%E5%AF%B9%E8%8B%AF%E4%BA%8C%E7%94%B2%E9%85%B8" title="对苯二甲酸">对苯二甲酸</a></li></ul></li> <li><a href="/wiki/%E8%8B%AF%E4%BA%8C%E8%83%BA" title="苯二胺">苯二胺</a> <ul><li><a href="/wiki/%E9%82%BB%E8%8B%AF%E4%BA%8C%E8%83%BA" title="邻苯二胺">邻苯二胺</a></li> <li><a href="/wiki/%E9%97%B4%E8%8B%AF%E4%BA%8C%E8%83%BA" title="间苯二胺">间苯二胺</a></li> <li><a href="/wiki/%E5%AF%B9%E8%8B%AF%E4%BA%8C%E8%83%BA" class="mw-redirect" title="对苯二胺">对苯二胺</a></li></ul></li> <li><a href="/wiki/%E7%94%B2%E8%8B%AF%E8%83%BA" title="甲苯胺">甲苯胺</a> <ul><li><a href="/wiki/%E9%82%BB%E7%94%B2%E8%8B%AF%E8%83%BA" title="邻甲苯胺">邻甲苯胺</a></li> <li><a href="/w/index.php?title=%E9%97%B4%E7%94%B2%E8%8B%AF%E8%83%BA&action=edit&redlink=1" class="new" title="间甲苯胺（页面不存在）">间甲苯胺</a></li> <li><a href="/wiki/4-%E7%94%B2%E5%9F%BA%E8%8B%AF%E8%83%BA" title="4-甲基苯胺">对甲苯胺</a></li></ul></li> <li><a href="/w/index.php?title=%E9%97%B4%E8%8B%AF%E4%BA%8C%E7%A3%BA%E9%85%B8&action=edit&redlink=1" class="new" title="间苯二磺酸（页面不存在）">间苯二磺酸</a></li> <li><a href="/wiki/%E5%AF%B9%E7%94%B2%E8%8B%AF%E7%A3%BA%E9%85%B8" title="对甲苯磺酸">对甲苯磺酸</a></li> <li><a href="/wiki/%E5%AF%B9%E6%B0%A8%E5%9F%BA%E8%8B%AF%E7%94%B2%E9%85%B8" title="对氨基苯甲酸">对氨基苯甲酸</a></li> <li><a href="/wiki/%E6%B0%B4%E6%A5%8A%E9%85%B8" title="水楊酸">水楊酸</a></li> <li><a href="/wiki/%E4%B9%99%E9%85%B0%E6%B0%B4%E6%9D%A8%E9%85%B8" title="乙酰水杨酸">乙酰水杨酸</a></li> <li><a href="/wiki/%E5%AF%B9%E4%B9%99%E9%85%B0%E6%B0%A8%E5%9F%BA%E9%85%9A" title="对乙酰氨基酚">对乙酰氨基酚</a></li> <li><a href="/wiki/%E9%9D%9E%E9%82%A3%E8%A5%BF%E4%B8%81" title="非那西丁">非那西丁</a></li> <li><a href="/wiki/%E9%97%B4%E6%B0%AF%E8%BF%87%E6%B0%A7%E8%8B%AF%E7%94%B2%E9%85%B8" title="间氯过氧苯甲酸">间氯过氧苯甲酸</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">多取代苯</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E4%B8%89%E7%94%B2%E8%8B%AF" title="三甲苯">三甲苯</a> <ul><li><a href="/wiki/%E5%9D%87%E4%B8%89%E7%94%B2%E8%8B%AF" title="均三甲苯">均三甲苯</a></li> <li><a href="/wiki/%E5%81%8F%E4%B8%89%E7%94%B2%E8%8B%AF" title="偏三甲苯">偏三甲苯</a></li> <li><a href="/wiki/%E8%BF%9E%E4%B8%89%E7%94%B2%E8%8B%AF" title="连三甲苯">连三甲苯</a></li></ul></li> <li><a href="/wiki/%E5%9B%9B%E7%94%B2%E8%8B%AF" title="四甲苯">四甲苯</a> <ul><li><a href="/wiki/%E5%9D%87%E5%9B%9B%E7%94%B2%E8%8B%AF" title="均四甲苯">均四甲苯</a></li> <li><a href="/wiki/%E5%81%8F%E5%9B%9B%E7%94%B2%E8%8B%AF" title="偏四甲苯">偏四甲苯</a></li> <li><a href="/wiki/%E9%80%A3%E5%9B%9B%E7%94%B2%E8%8B%AF" title="連四甲苯">连四甲苯</a></li></ul></li> <li><a href="/wiki/%E4%BA%94%E7%94%B2%E8%8B%AF" title="五甲苯">五甲苯</a></li> <li><a href="/wiki/%E5%85%AD%E7%94%B2%E8%8B%AF" title="六甲苯">六甲苯</a></li> <li><a href="/wiki/%E6%B2%A1%E9%A3%9F%E5%AD%90%E9%85%B8" title="没食子酸">没食子酸</a></li> <li><a href="/wiki/%E9%96%93%E8%8B%AF%E4%B8%89%E9%85%9A%E7%BE%A7%E9%85%B8" title="間苯三酚羧酸">间苯三酚羧酸</a></li> <li><a href="/wiki/%E8%8B%AF%E4%B8%89%E9%85%9A" title="苯三酚">苯三酚</a> <ul><li><a href="/wiki/%E8%BF%9E%E8%8B%AF%E4%B8%89%E9%85%9A" title="连苯三酚">连苯三酚</a></li> <li><a href="/wiki/%E5%81%8F%E8%8B%AF%E4%B8%89%E9%85%9A" title="偏苯三酚">偏苯三酚</a></li> <li><a href="/wiki/%E5%9D%87%E8%8B%AF%E4%B8%89%E9%85%9A" title="均苯三酚">均苯三酚</a></li></ul></li> <li><a href="/wiki/%E8%8B%A6%E5%91%B3%E9%85%B8" title="苦味酸">苦味酸</a></li> <li><a href="/wiki/%E4%B8%89%E7%A1%9D%E5%9F%BA%E7%94%B2%E8%8B%AF" title="三硝基甲苯">三硝基甲苯</a></li> <li><a href="/wiki/2,4,6-%E4%B8%89%E7%A1%9D%E5%9F%BA%E8%8B%AF%E8%83%BA" title="2,4,6-三硝基苯胺">三硝基苯胺</a></li> <li><a href="/wiki/%E4%B8%89%E6%BA%B4%E8%8B%AF%E9%85%9A" title="三溴苯酚">三溴苯酚</a></li> <li><a href="/wiki/%E4%BA%94%E6%B0%AF%E9%85%9A" title="五氯酚">五氯酚</a></li> <li><a href="/wiki/%E8%8B%AF%E4%BA%94%E9%85%9A" title="苯五酚">苯五酚</a></li> <li><a href="/wiki/%E8%8B%AF%E5%85%AD%E9%85%9A" title="苯六酚">苯六酚</a></li> <li><a href="/wiki/%E5%85%AD%E6%B0%9F%E8%8B%AF" title="六氟苯">六氟苯</a></li> <li><a href="/wiki/%E5%85%AD%E6%B0%AF%E8%8B%AF" title="六氯苯">六氯苯</a></li> <li><a href="/wiki/%E5%85%AD%E6%BA%B4%E8%8B%AF" title="六溴苯">六溴苯</a></li> <li><a href="/wiki/%E5%85%AD%E7%A2%98%E8%8B%AF" title="六碘苯">六碘苯</a></li> <li><a href="/wiki/%E8%8B%AF%E5%85%AD%E7%94%B2%E9%85%B8" title="苯六甲酸">苯六甲酸</a></li> <li><a href="/wiki/1,3,5-%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%8B%AF" title="1,3,5-三苯基苯">1,3,5-三苯基苯</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">苯的异构体</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E6%9D%9C%E7%93%A6%E8%8B%AF" title="杜瓦苯">杜瓦苯</a></li> <li><a href="/wiki/%E7%9B%86%E8%8B%AF" title="盆苯">盆苯</a></li> <li><a href="/wiki/%E6%A3%B1%E6%99%B6%E7%83%B7" title="棱晶烷">棱晶烷</a></li> <li><a href="/wiki/%E5%85%8B%E5%8A%B3%E6%96%AF%E8%8B%AF" title="克劳斯苯">克劳斯苯</a></li> <li><a href="/wiki/%E8%81%94%E7%8E%AF%E4%B8%99%E7%83%AF" title="联环丙烯">联环丙烯</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">化合物</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E8%81%94%E8%8B%AF" title="联苯">联苯</a></li> <li><a href="/wiki/%E4%B8%89%E8%81%94%E8%8B%AF" title="三联苯">三联苯</a></li></ul> <ul><li><a href="/wiki/%E8%90%98" title="萘">萘</a></li> <li><a href="/wiki/%E8%92%BD" title="蒽">蒽</a></li> <li><a href="/wiki/%E8%8F%B2" title="菲">菲</a></li> <li><a href="/wiki/%E8%92%84" title="蒄">蒄</a></li> <li><a href="/wiki/%E5%A4%9A%E7%92%B0%E8%8A%B3%E9%A6%99%E7%83%B4" title="多環芳香烴">稠环芳烃</a></li></ul> <ul><li><a href="/wiki/%E8%8B%AF%E7%82%94" title="苯炔">苯炔</a></li> <li><a href="/wiki/%E8%8B%AF%E9%86%8C" title="苯醌">苯醌</a> <ul><li><a href="/wiki/1,2-%E8%8B%AF%E9%86%8C" title="1,2-苯醌">邻苯醌</a></li> <li><a href="/wiki/1,4-%E8%8B%AF%E9%86%8C" title="1,4-苯醌">对苯醌</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">相关条目</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E8%8B%AF%E5%9F%BA" title="苯基">苯基</a></li> <li><a href="/wiki/%E8%8B%84%E5%9F%BA" title="苄基">苄基</a></li> <li><a href="/wiki/%E8%8A%B3%E5%9F%BA" title="芳基">芳基</a></li> <li><a href="/wiki/%E8%8A%B3%E9%A6%99%E6%80%A7" title="芳香性">芳香性</a></li> <li><a href="/wiki/%E8%8A%B3%E9%A6%99%E7%8E%AF" title="芳香环">芳香环</a></li> <li><a href="/wiki/%E8%8B%AF%E7%8E%AF%E7%9A%84%E4%BA%B2%E7%94%B5%E5%8F%96%E4%BB%A3%E5%AE%9A%E4%BD%8D%E6%95%88%E5%BA%94" title="苯环的亲电取代定位效应">定位规则</a></li> <li><a href="/wiki/%E4%BA%B2%E7%94%B5%E8%8A%B3%E9%A6%99%E5%8F%96%E4%BB%A3" title="亲电芳香取代">亲电芳香取代反应</a></li> <li><a href="/wiki/%E8%8A%B3%E9%A6%99%E6%97%8F%E4%BA%B2%E6%A0%B8%E5%8F%96%E4%BB%A3%E5%8F%8D%E5%BA%94" title="芳香族亲核取代反应">亲核芳香取代反应</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84265675"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84261037"></div><div role="navigation" class="navbox" aria-labelledby="咽喉製劑(R02)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="collapsible-title navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84265675"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84244141"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:%E5%92%BD%E5%96%89%E5%88%B6%E5%89%82" title="Template:咽喉制剂"><abbr title="查看该模板">查</abbr></a></li><li class="nv-talk"><a href="/w/index.php?title=Template_talk:%E5%92%BD%E5%96%89%E5%88%B6%E5%89%82&action=edit&redlink=1" class="new" title="Template talk:咽喉制剂（页面不存在）"><abbr title="讨论该模板">论</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:%E7%BC%96%E8%BE%91%E9%A1%B5%E9%9D%A2/Template:%E5%92%BD%E5%96%89%E5%88%B6%E5%89%82" title="Special:编辑页面/Template:咽喉制剂"><abbr title="编辑该模板">编</abbr></a></li></ul></div><div id="咽喉製劑(R02)" style="font-size:110%;margin:0 5em"><a href="/wiki/%E5%92%BD%E5%96%89" title="咽喉">咽喉</a>製劑(<a href="/w/index.php?title=ATC_code_R02&action=edit&redlink=1" class="new" title="ATC code R02（页面不存在）">R02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%E6%8A%97%E8%8F%8C%E5%8A%91" title="抗菌劑">抗菌劑</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E5%90%96%E5%95%B6%E9%BB%83" title="吖啶黃">吖啶黃</a></li> <li><a href="/w/index.php?title=%E5%AE%89%E5%B7%B4%E8%85%99&action=edit&redlink=1" class="new" title="安巴腙（页面不存在）">安巴腙</a></li> <li><a href="/wiki/%E6%88%8A%E9%97%B4%E7%94%B2%E9%85%9A" title="戊间甲酚">戊間甲酚</a></li> <li><a href="/wiki/%E8%8B%AF%E6%89%8E%E6%B0%AF%E9%93%B5" title="苯扎氯铵">苯扎氯铵</a></li> <li><a href="/w/index.php?title=%E8%8A%90%E7%B4%A2%E6%B0%AF%E9%8A%A8&action=edit&redlink=1" class="new" title="芐索氯銨（页面不存在）">芐索氯銨</a></li> <li><a href="/wiki/%E8%A5%BF%E6%9B%B2%E9%93%B5" title="西曲铵">西曲铵</a> (<a href="/wiki/%E6%BA%B4%E5%8C%96%E5%8D%81%E5%85%AD%E7%83%B7%E5%9F%BA%E4%B8%89%E7%94%B2%E9%93%B5" title="溴化十六烷基三甲铵">溴化十六烷基三甲铵</a>/<a href="/wiki/%E5%8D%81%E5%85%AD%E7%83%B7%E5%9F%BA%E4%B8%89%E7%94%B2%E5%9F%BA%E6%B0%AF%E5%8C%96%E9%93%B5" title="十六烷基三甲基氯化铵">十六烷基三甲基氯化铵</a>)</li> <li><a href="/wiki/%E8%A5%BF%E5%90%A1%E6%B0%AF%E9%93%B5" title="西吡氯铵">西吡氯铵</a></li> <li><a href="/wiki/%E6%B0%AF%E5%B7%B1%E5%AE%9A" title="氯己定">氯己定</a></li> <li><a href="/w/index.php?title=%E4%BA%8C%E6%B0%AF%E7%94%B2%E7%BE%A5%E5%96%B9&action=edit&redlink=1" class="new" title="二氯甲羥喹（页面不存在）">二氯甲羥喹</a></li> <li><a href="/wiki/%E5%9C%B0%E5%96%B9%E6%B0%AF%E9%93%B5" title="地喹氯铵">地喹氯铵</a></li> <li><a href="/w/index.php?title=2,4-%E4%BA%8C%E6%B0%AF%E8%8B%AF%E7%94%B2%E5%9F%BA%E9%86%87&action=edit&redlink=1" class="new" title="2,4-二氯苯甲基醇（页面不存在）">2,4-二氯苯甲基醇</a></li> <li><a href="/wiki/%E5%B7%B1%E8%84%92%E5%AE%9A" title="己脒定">己脒定</a></li> <li><a href="/wiki/4-%E5%B7%B1%E5%9F%BA%E9%97%B4%E8%8B%AF%E4%BA%8C%E9%85%9A" title="4-己基间苯二酚">4-己基间苯二酚</a></li> <li><a href="/w/index.php?title=%E8%82%89%E8%8D%B3%E8%94%BB-%E8%8B%AF%E6%89%8E&action=edit&redlink=1" class="new" title="肉荳蔻-苯扎（页面不存在）">肉荳蔻-苯扎</a></li> <li><a href="/wiki/8-%E7%BE%9F%E5%9F%BA%E5%96%B9%E5%95%89" title="8-羟基喹啉">8-羟基喹啉</a></li> <li><a class="mw-selflink selflink">苯酚</a></li> <li><a href="/wiki/%E8%81%9A%E7%BB%B4%E9%85%AE%E7%A2%98" title="聚维酮碘">聚维酮碘</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%E6%8A%97%E7%BB%86%E8%8F%8C%E8%8D%AF" title="抗细菌药">抗细菌药</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E6%9D%86%E8%8F%8C%E8%82%BD" title="杆菌肽">杆菌肽</a></li> <li><a href="/w/index.php?title=%E9%90%AE%E5%AD%A2%E7%9C%9F%E8%8F%8C%E7%B4%A0&action=edit&redlink=1" class="new" title="鐮孢真菌素（页面不存在）">鐮孢真菌素</a></li> <li><a href="/w/index.php?title=%E7%9F%AD%E6%9D%86%E8%8F%8C%E8%82%BD&action=edit&redlink=1" class="new" title="短杆菌肽（页面不存在）">短杆菌肽</a></li> <li><a href="/wiki/%E6%96%B0%E9%9C%89%E7%B4%A0" title="新霉素">新霉素</a></li> <li><a href="/w/index.php?title=%E7%9F%AD%E6%A1%BF%E8%8F%8C%E7%B4%A0&action=edit&redlink=1" class="new" title="短桿菌素（页面不存在）">短桿菌素</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%E5%B1%80%E9%83%A8%E9%BA%BB%E9%86%89%E8%8D%AF" title="局部麻醉药">局部麻醉药</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E8%8B%AF%E4%BD%90%E5%8D%A1%E5%9B%A0" title="苯佐卡因">苯佐卡因</a></li> <li><a href="/wiki/%E5%8F%AF%E5%8D%A1%E5%9B%A0" title="可卡因">可卡因</a></li> <li><a href="/w/index.php?title=%E9%81%94%E5%85%8B%E7%BE%85%E5%AF%A7&action=edit&redlink=1" class="new" title="達克羅寧（页面不存在）">達克羅寧</a></li> <li><a href="/wiki/%E5%88%A9%E5%A4%9A%E5%8D%A1%E5%9B%A0" title="利多卡因">利多卡因</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">其他藥劑</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/w/index.php?title=%E6%B0%9F%E8%81%AF%E8%8B%AF%E4%B8%99%E9%85%B8&action=edit&redlink=1" class="new" title="氟聯苯丙酸（页面不存在）">氟聯苯丙酸</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84265675"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84261037"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84265675"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84244141"></div><div role="navigation" class="navbox" aria-labelledby="血管保护药_（C05）" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="collapsible-title navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84265675"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84244141"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:%E8%A1%80%E7%AE%A1%E4%BF%9D%E6%8A%A4%E8%8D%AF" title="Template:血管保护药"><abbr title="查看该模板">查</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:%E8%A1%80%E7%AE%A1%E4%BF%9D%E6%8A%A4%E8%8D%AF" title="Template talk:血管保护药"><abbr title="讨论该模板">论</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:%E7%BC%96%E8%BE%91%E9%A1%B5%E9%9D%A2/Template:%E8%A1%80%E7%AE%A1%E4%BF%9D%E6%8A%A4%E8%8D%AF" title="Special:编辑页面/Template:血管保护药"><abbr title="编辑该模板">编</abbr></a></li></ul></div><div id="血管保护药_（C05）" style="font-size:110%;margin:0 5em"><a href="/w/index.php?title=%E8%A1%80%E7%AE%A1%E4%BF%9D%E6%8A%A4%E8%8D%AF&action=edit&redlink=1" class="new" title="血管保护药（页面不存在）">血管保护药</a> （<a href="/wiki/ATC%E4%BB%A3%E7%A0%81_(C05)" title="ATC代码 (C05)">C05</a>）</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:MistyRose;">外用的<a href="/wiki/%E7%97%94" class="mw-redirect" title="痔">痔疮</a>药</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"><b><a href="/w/index.php?title=%E7%9A%AE%E8%B4%A8%E7%B1%BB%E5%9B%BA%E9%86%87%E7%B1%BB&action=edit&redlink=1" class="new" title="皮质类固醇类（页面不存在）">皮质类固醇类</a></b> （<a href="/wiki/%E6%B0%A2%E5%8C%96%E5%8F%AF%E7%9A%84%E6%9D%BE" class="mw-redirect" title="氢化可的松">氢化可的松</a>、<a href="/wiki/%E6%B3%BC%E5%B0%BC%E6%9D%BE%E9%BE%99" title="泼尼松龙">泼尼松龙</a>、<a href="/wiki/%E5%80%8D%E4%BB%96%E7%B1%B3%E6%9D%BE" title="倍他米松">倍他米松</a>、<a href="/w/index.php?title=%E6%B0%9F%E7%B1%B3%E9%BE%99&action=edit&redlink=1" class="new" title="氟米龙（页面不存在）">氟米龙</a>、<a href="/w/index.php?title=%E6%B0%9F%E5%8F%AF%E9%BE%99&action=edit&redlink=1" class="new" title="氟可龙（页面不存在）">氟可龙</a>、<a href="/wiki/%E5%9C%B0%E5%A1%9E%E7%B1%B3%E6%9D%BE" title="地塞米松">地塞米松</a>、<a href="/w/index.php?title=%E6%B0%9F%E8%BD%BB%E6%9D%BE&action=edit&redlink=1" class="new" title="氟轻松（页面不存在）">氟轻松</a>、<a href="/wiki/%E9%86%8B%E9%85%B8%E6%B0%9F%E8%BD%BB%E6%9D%BE" title="醋酸氟轻松">醋酸氟轻松</a>） <p><b><a href="/wiki/%E5%B1%80%E9%83%A8%E9%BA%BB%E9%86%89%E8%8D%AF" title="局部麻醉药">局部麻醉药</a></b> （<a href="/wiki/%E5%88%A9%E5%A4%9A%E5%8D%A1%E5%9B%A0" title="利多卡因">利多卡因</a>、<a href="/wiki/%E4%B8%81%E5%8D%A1%E5%9B%A0" title="丁卡因">丁卡因</a>、<a href="/wiki/%E8%8B%AF%E4%BD%90%E5%8D%A1%E5%9B%A0" title="苯佐卡因">苯佐卡因</a>、<a href="/w/index.php?title=%E8%BE%9B%E5%8F%AF%E5%8D%A1%E5%9B%A0&action=edit&redlink=1" class="new" title="辛可卡因（页面不存在）">辛可卡因</a>、<a href="/wiki/%E6%99%AE%E9%B2%81%E5%8D%A1%E5%9B%A0" title="普鲁卡因">普鲁卡因</a>、<a href="/wiki/%E5%A5%A5%E6%98%94%E5%8D%A1%E5%9B%A0" title="奥昔卡因">奥昔卡因</a>、<a href="/w/index.php?title=%E6%99%AE%E8%8E%AB%E5%8D%A1%E5%9B%A0&action=edit&redlink=1" class="new" title="普莫卡因（页面不存在）">普莫卡因</a>） </p> <b>其他</b> （<a href="/wiki/%E4%B8%89%E8%8B%84%E7%B3%96%E8%8B%B7" title="三苄糖苷">三苄糖苷</a>）</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:MistyRose;">抗静脉曲张药</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"><b>局部用药的<a href="/wiki/%E8%82%9D%E7%B4%A0" title="肝素">肝素</a>或<a href="/w/index.php?title=%E7%B1%BB%E8%82%9D%E7%B4%A0&action=edit&redlink=1" class="new" title="类肝素（页面不存在）">类肝素</a></b> （<a href="/w/index.php?title=%E6%9C%89%E6%9C%BA%E7%B1%BB%E8%82%9D%E7%B4%A0&action=edit&redlink=1" class="new" title="有机类肝素（页面不存在）">有机类肝素</a>、<a href="/w/index.php?title=%E9%98%BF%E6%9C%B4%E9%85%B8%E9%92%A0&action=edit&redlink=1" class="new" title="阿朴酸钠（页面不存在）">阿朴酸钠</a>、<a href="/wiki/%E8%82%9D%E7%B4%A0" title="肝素">肝素</a>、<a href="/w/index.php?title=%E6%9C%A8%E8%81%9A%E7%A1%AB%E9%92%A0&action=edit&redlink=1" class="new" title="木聚硫钠（页面不存在）">木聚硫钠</a>） <p><b>局部注射硬化剂</b> （<a href="/w/index.php?title=%E6%B2%B9%E9%85%B8%E5%8D%95%E4%B9%99%E9%86%87%E8%83%BA&action=edit&redlink=1" class="new" title="油酸单乙醇胺（页面不存在）">油酸单乙醇胺</a>、<a href="/w/index.php?title=%E8%81%9A%E6%A1%82%E9%86%87&action=edit&redlink=1" class="new" title="聚桂醇（页面不存在）">聚桂醇</a>、<a href="/wiki/%E8%BD%89%E5%8C%96%E7%B3%96" class="mw-redirect" title="轉化糖">转化糖</a>、<a href="/w/index.php?title=%E5%8D%81%E5%9B%9B%E7%83%B7%E7%A1%AB%E9%85%B8%E9%92%A0&action=edit&redlink=1" class="new" title="十四烷硫酸钠（页面不存在）">十四烷硫酸钠</a>、<a class="mw-selflink selflink">苯酚</a>） </p> <b>其他</b> （<a href="/w/index.php?title=%E7%BE%9F%E8%8B%AF%E7%A3%BA%E9%85%B8%E9%92%99&action=edit&redlink=1" class="new" title="羟苯磺酸钙（页面不存在）">羟苯磺酸钙</a>）</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:MistyRose;">毛细血管稳定药</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"><b><a href="/w/index.php?title=%E7%94%9F%E7%89%A9%E9%BB%84%E9%85%AE%E7%B4%A0&action=edit&redlink=1" class="new" title="生物黄酮素（页面不存在）">生物黄酮素</a></b> （<a href="/w/index.php?title=%E4%B9%99%E5%90%97%E8%8A%A6%E4%B8%81&action=edit&redlink=1" class="new" title="乙吗芦丁（页面不存在）">乙吗芦丁</a>、<a href="/w/index.php?title=%E8%8E%AB%E8%AF%BA%E8%8A%A6%E4%B8%81&action=edit&redlink=1" class="new" title="莫诺芦丁（页面不存在）">莫诺芦丁</a>、<a href="/w/index.php?title=%E5%9C%B0%E5%A5%A5%E5%8F%B8%E6%98%8E&action=edit&redlink=1" class="new" title="地奥司明（页面不存在）">地奥司明</a>、<a href="/w/index.php?title=%E6%9B%B2%E5%85%8B%E8%8A%A6%E4%B8%81&action=edit&redlink=1" class="new" title="曲克芦丁（页面不存在）">曲克芦丁</a>、<a href="/w/index.php?title=%E6%B5%B7%E6%9B%B2%E5%8F%B8%E6%98%8E&action=edit&redlink=1" class="new" title="海曲司明（页面不存在）">海曲司明</a>） - <b>其他</b> （<a href="/wiki/%E4%B8%89%E8%8B%84%E7%B3%96%E8%8B%B7" title="三苄糖苷">三苄糖苷</a>、<a href="/w/index.php?title=%E9%85%9A%E7%A3%BA%E4%B9%99%E8%83%BA&action=edit&redlink=1" class="new" title="酚磺乙胺（页面不存在）">酚磺乙胺</a>）</div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="center"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Vascular_navs" title="Template:Vascular navs"><abbr title="查看该模板">查</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Vascular_navs" title="Template talk:Vascular navs"><abbr title="讨论该模板">论</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:%E7%BC%96%E8%BE%91%E9%A1%B5%E9%9D%A2/Template:Vascular_navs" title="Special:编辑页面/Template:Vascular navs"><abbr title="编辑该模板">编</abbr></a></li></ul></div><div id="循环系统索引" style="font-size:110%;margin:0 5em"><a href="/wiki/%E5%BE%AA%E7%8E%AF%E7%B3%BB%E7%BB%9F" title="循环系统">循环系统</a>索引</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">描述</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/Template:%E5%8A%A8%E8%84%89%E4%B8%8E%E9%9D%99%E8%84%89" title="Template:动脉与静脉">解剖</a></li> <li><a href="/wiki/%E5%8A%A8%E8%84%89" title="动脉">动脉</a> <ul><li><a href="/wiki/Template:Arteries_of_head_and_neck" title="Template:Arteries of head and neck">頭頸部</a></li> <li><a href="/wiki/Template:Arteries_of_upper_limbs" title="Template:Arteries of upper limbs">上肢</a></li> <li><a href="/wiki/Template:%E8%83%B8%E9%83%A8%E5%8B%95%E8%84%88" title="Template:胸部動脈">胸</a></li> <li><a href="/wiki/Template:Arteries_of_abdomen" title="Template:Arteries of abdomen">腹</a></li> <li><a href="/wiki/Template:Arteries_of_lower_limbs" title="Template:Arteries of lower limbs">下肢</a></li></ul></li> <li><a href="/wiki/%E9%9D%99%E8%84%89" title="静脉">静脉</a> <ul><li><a href="/wiki/Template:%E9%A0%AD%E9%A0%B8%E9%83%A8%E9%9D%9C%E8%84%88" title="Template:頭頸部靜脈">頭頸部</a></li> <li><a href="/wiki/Template:%E4%B8%8A%E8%82%A2%E9%9D%9C%E8%84%88" title="Template:上肢靜脈">上肢</a></li> <li><a href="/wiki/Template:%E8%83%B8%E9%83%A8%E9%9D%9C%E8%84%88" title="Template:胸部靜脈">胸</a></li> <li><a href="/wiki/Template:%E8%85%B9%E9%83%A8%E5%8F%8A%E9%AA%A8%E7%9B%86%E4%B9%8B%E9%9D%9C%E8%84%88" title="Template:腹部及骨盆之靜脈">腹骨盆</a></li> <li><a href="/wiki/Template:%E4%B8%8B%E8%82%A2%E9%9D%9C%E8%84%88" title="Template:下肢靜脈">下肢</a></li></ul></li> <li><span class="ilh-all" data-orig-title="Template:Development of mammalian circulatory system" data-lang-code="en" data-lang-name="英语" data-foreign-title="Template:Development of mammalian circulatory system"><span class="ilh-page"><a href="/w/index.php?title=Template:Development_of_mammalian_circulatory_system&action=edit&redlink=1" class="new" title="Template:Development of mammalian circulatory system（页面不存在）">發育</a></span><span class="noprint ilh-comment">（<span class="ilh-lang">英语</span><span class="ilh-colon">：</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Template:Development_of_mammalian_circulatory_system" class="extiw" title="en:Template:Development of mammalian circulatory system"><span lang="en" dir="auto">Template:Development of mammalian circulatory system</span></a></span>）</span></span></li> <li><a href="/wiki/Template:Human_cell_types_derived_primarily_from_mesoderm" class="mw-redirect" title="Template:Human cell types derived primarily from mesoderm">細胞</a></li> <li><a href="/wiki/Template:Cardiovascular_physiology" class="mw-redirect" title="Template:Cardiovascular physiology">生理</a> <ul><li><span class="ilh-all" data-orig-title="Template:Angiogenic proteins" data-lang-code="en" data-lang-name="英语" data-foreign-title="Template:Angiogenic proteins"><span class="ilh-page"><a href="/w/index.php?title=Template:Angiogenic_proteins&action=edit&redlink=1" class="new" title="Template:Angiogenic proteins（页面不存在）">蛋白質</a></span><span class="noprint ilh-comment">（<span class="ilh-lang">英语</span><span class="ilh-colon">：</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Template:Angiogenic_proteins" class="extiw" title="en:Template:Angiogenic proteins"><span lang="en" dir="auto">Template:Angiogenic proteins</span></a></span>）</span></span></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">疾病</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><span class="ilh-all" data-orig-title="Template:Congenital vascular defects" data-lang-code="en" data-lang-name="英语" data-foreign-title="Template:Congenital vascular defects"><span class="ilh-page"><a href="/w/index.php?title=Template:Congenital_vascular_defects&action=edit&redlink=1" class="new" title="Template:Congenital vascular defects（页面不存在）">先天</a></span><span class="noprint ilh-comment">（<span class="ilh-lang">英语</span><span class="ilh-colon">：</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Template:Congenital_vascular_defects" class="extiw" title="en:Template:Congenital vascular defects"><span lang="en" dir="auto">Template:Congenital vascular defects</span></a></span>）</span></span></li> <li><a href="/wiki/Template:%E5%BE%AA%E7%8E%AF%E7%AE%A1%E9%81%93%E7%98%A4" title="Template:循环管道瘤">腫瘤</a></li> <li><a href="/wiki/Template:%E6%B7%8B%E5%B7%B4%E7%B3%BB%E7%BB%9F%E7%96%BE%E7%97%85" title="Template:淋巴系统疾病">淋巴系統</a></li> <li><span class="ilh-all" data-orig-title="Template:Chest trauma" data-lang-code="en" data-lang-name="英语" data-foreign-title="Template:Chest trauma"><span class="ilh-page"><a href="/w/index.php?title=Template:Chest_trauma&action=edit&redlink=1" class="new" title="Template:Chest trauma（页面不存在）">受傷</a></span><span class="noprint ilh-comment">（<span class="ilh-lang">英语</span><span class="ilh-colon">：</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Template:Chest_trauma" class="extiw" title="en:Template:Chest trauma"><span lang="en" dir="auto">Template:Chest trauma</span></a></span>）</span></span></li> <li><a href="/wiki/Template:Systemic_vasculitis" class="mw-redirect" title="Template:Systemic vasculitis">血管炎</a></li> <li><a href="/wiki/Template:%E8%A1%80%E7%AE%A1%E7%96%BE%E7%97%85" title="Template:血管疾病">其他</a></li> <li><a href="/wiki/Template:Cardiovascular_system_symptoms_and_signs" title="Template:Cardiovascular system symptoms and signs">症狀</a> <ul><li><a href="/wiki/Template:Eponymous_medical_signs_for_cardiovascular_system" class="mw-redirect" title="Template:Eponymous medical signs for cardiovascular system">齊名</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">治療</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><span class="ilh-all" data-orig-title="Template:Vascular procedures" data-lang-code="en" data-lang-name="英语" data-foreign-title="Template:Vascular procedures"><span class="ilh-page"><a href="/w/index.php?title=Template:Vascular_procedures&action=edit&redlink=1" class="new" title="Template:Vascular procedures（页面不存在）">手术</a></span><span class="noprint ilh-comment">（<span class="ilh-lang">英语</span><span class="ilh-colon">：</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Template:Vascular_procedures" class="extiw" title="en:Template:Vascular procedures"><span lang="en" dir="auto">Template:Vascular procedures</span></a></span>）</span></span></li> <li>藥物 <ul><li><a href="/wiki/Template:%CE%92%E5%8F%97%E4%BD%93%E9%98%BB%E6%BB%9E%E5%89%82" 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