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href="/w/index.php?title=Special:%E5%88%9B%E5%BB%BA%E8%B4%A6%E6%88%B7&returnto=%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6" title="我们推荐您创建账号并登录，但这不是强制性的"><span class="vector-icon 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=%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6" 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-制备、结构与手性" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#制备、结构与手性"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>制备、结构与手性</span> </div> </a> <ul id="toc-制备、结构与手性-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-氧化和与硫属元素、卤族元素及酸的重要反应" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#氧化和与硫属元素、卤族元素及酸的重要反应"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>氧化和与硫属元素、卤族元素及酸的重要反应</span> </div> </a> <ul id="toc-氧化和与硫属元素、卤族元素及酸的重要反应-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-应用" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#应用"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>应用</span> </div> </a> <ul id="toc-应用-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">4</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">三苯基膦</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。21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-21" 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">21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-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AB%D9%84%D8%A7%D8%AB%D9%8A_%D9%81%D9%8A%D9%86%D9%8A%D9%84_%D8%A7%D9%84%D9%81%D9%88%D8%B3%D9%81%D9%8A%D9%86" title="ثلاثي فينيل الفوسفين – 阿拉伯语" lang="ar" hreflang="ar" data-title="ثلاثي فينيل الفوسفين" 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-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AA%D8%B1%DB%8C%E2%80%8C%D9%81%D9%86%DB%8C%D9%84%D9%81%D9%88%D8%B3%D9%81%DB%8C%D9%86" title="تری‌فنیلفوسفین – South Azerbaijani" lang="azb" hreflang="azb" data-title="تری‌فنیلفوسفین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Trifenylfosfin" title="Trifenylfosfin – 捷克语" lang="cs" hreflang="cs" data-title="Trifenylfosfin" 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-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Triphenylphosphan" title="Triphenylphosphan – 德语" lang="de" hreflang="de" data-title="Triphenylphosphan" data-language-autonym="Deutsch" data-language-local-name="德语" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Triphenylphosphine" title="Triphenylphosphine – 英语" lang="en" hreflang="en" data-title="Triphenylphosphine" data-language-autonym="English" data-language-local-name="英语" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Trifenilfosfano" title="Trifenilfosfano – 西班牙语" lang="es" hreflang="es" data-title="Trifenilfosfano" 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-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%D8%B1%DB%8C%E2%80%8C%D9%81%D9%86%DB%8C%D9%84%E2%80%8C%D9%81%D8%B3%D9%81%DB%8C%D9%86" title="تری‌فنیل‌فسفین – 波斯语" lang="fa" hreflang="fa" data-title="تری‌فنیل‌فسفین" 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/Trifenyylifosfiini" title="Trifenyylifosfiini – 芬兰语" lang="fi" hreflang="fi" data-title="Trifenyylifosfiini" 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-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Triph%C3%A9nylphosphine" title="Triphénylphosphine – 法语" lang="fr" hreflang="fr" data-title="Triphénylphosphine" data-language-autonym="Français" data-language-local-name="法语" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Trifenilfoszfin" title="Trifenilfoszfin – 匈牙利语" lang="hu" hreflang="hu" data-title="Trifenilfoszfin" 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-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Trifenilfosfina" title="Trifenilfosfina – 印度尼西亚语" lang="id" hreflang="id" data-title="Trifenilfosfina" 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-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Trifenilfosfina" title="Trifenilfosfina – 意大利语" lang="it" hreflang="it" data-title="Trifenilfosfina" 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%88%E3%83%AA%E3%83%95%E3%82%A7%E3%83%8B%E3%83%AB%E3%83%9B%E3%82%B9%E3%83%95%E3%82%A3%E3%83%B3" title="トリフェニルホスフィン – 日语" lang="ja" hreflang="ja" data-title="トリフェニルホスフィン" 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-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Trifenylfosfine" title="Trifenylfosfine – 荷兰语" lang="nl" hreflang="nl" data-title="Trifenylfosfine" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Trifenilfosfina" title="Trifenilfosfina – 葡萄牙语" lang="pt" hreflang="pt" data-title="Trifenilfosfina" 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-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D1%80%D0%B8%D1%84%D0%B5%D0%BD%D0%B8%D0%BB%D1%84%D0%BE%D1%81%D1%84%D0%B8%D0%BD" title="Трифенилфосфин – 俄语" lang="ru" hreflang="ru" data-title="Трифенилфосфин" data-language-autonym="Русский" data-language-local-name="俄语" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Trifenilfosfin" title="Trifenilfosfin – 塞尔维亚-克罗地亚语" lang="sh" hreflang="sh" data-title="Trifenilfosfin" 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-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Trifenilfosfin" title="Trifenilfosfin – 塞尔维亚语" lang="sr" hreflang="sr" data-title="Trifenilfosfin" 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-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AE%E0%AF%81%E0%AE%AA%E0%AF%8D%E0%AE%AA%E0%AF%80%E0%AE%A9%E0%AF%88%E0%AE%B2%E0%AF%8D_%E0%AE%AA%E0%AE%BE%E0%AE%9A%E0%AF%81%E0%AE%AA%E0%AF%80%E0%AE%A9%E0%AF%8D" title="முப்பீனைல் பாசுபீன் – 泰米尔语" lang="ta" hreflang="ta" data-title="முப்பீனைல் பாசுபீன்" 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-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Trifenilfosfin" title="Trifenilfosfin – 土耳其语" lang="tr" hreflang="tr" data-title="Trifenilfosfin" 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%A2%D1%80%D0%B8%D1%84%D0%B5%D0%BD%D1%96%D0%BB%D1%84%D0%BE%D1%81%D1%84%D1%96%D0%BD" title="Трифенілфосфін – 乌克兰语" lang="uk" hreflang="uk" data-title="Трифенілфосфін" data-language-autonym="Українська" data-language-local-name="乌克兰语" class="interlanguage-link-target"><span>Українська</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6&action=show-download-screen"><span>下载为PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="javascript:print();" rel="alternate" title="本页面的可打印版本[p]" accesskey="p"><span>打印页面</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> 在其他项目中 </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Triphenylphosphine" hreflang="en"><span>维基共享资源</span></a></li><li class="wb-otherproject-link wb-otherproject-wikiversity mw-list-item"><a href="https://zh.wikiversity.org/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6" hreflang="zh"><span>维基学院</span></a></li><li id="t-wikibase" class="wb-otherproject-link 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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" data-event-name="pinnable-header.vector-appearance.pin">移至侧栏</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">隐藏</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">维基百科，自由的百科全书</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="zh" dir="ltr"><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;">三苯基磷 </th></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><a href="/wiki/File:Triphenylphosphine_structure.svg" class="mw-file-description" title="三苯基磷"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Triphenylphosphine_structure.svg/200px-Triphenylphosphine_structure.svg.png" decoding="async" width="200" height="192" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Triphenylphosphine_structure.svg/300px-Triphenylphosphine_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Triphenylphosphine_structure.svg/400px-Triphenylphosphine_structure.svg.png 2x" data-file-width="763" data-file-height="732" /></a></span> </td></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><a href="/wiki/File:Triphenylphosphine-ray-3D-balls.png" class="mw-file-description" title="三苯基磷分子的球棒模型"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Triphenylphosphine-ray-3D-balls.png/200px-Triphenylphosphine-ray-3D-balls.png" decoding="async" width="200" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Triphenylphosphine-ray-3D-balls.png/300px-Triphenylphosphine-ray-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Triphenylphosphine-ray-3D-balls.png/400px-Triphenylphosphine-ray-3D-balls.png 2x" data-file-width="787" data-file-height="738" /></a></span> </td></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><a href="/wiki/File:Sample_of_triphenylphosphine.jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Sample_of_triphenylphosphine.jpg/200px-Sample_of_triphenylphosphine.jpg" decoding="async" width="200" height="285" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Sample_of_triphenylphosphine.jpg/300px-Sample_of_triphenylphosphine.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Sample_of_triphenylphosphine.jpg/400px-Sample_of_triphenylphosphine.jpg 2x" data-file-width="3093" data-file-height="4413" /></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 />Triphenylphosphine </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=603-35-0">603-35-0</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/11776">11776</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/11283">11283</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">c3c(P(c1ccccc1)c2ccccc2)cccc3</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/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H</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">InChIKey</a> </td> <td><small>RIOQSEWOXXDEQQ-UHFFFAOYAH</small> </td></tr> <tr> <td><a href="/wiki/%E6%AC%A7%E7%9B%9F%E7%BC%96%E5%8F%B7" class="mw-redirect" title="欧盟编号">EINECS</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://ecb.jrc.ec.europa.eu/esis/index.php?GENRE=ECNO&ENTREE=210-036-0">210-036-0</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>SZ3500000 </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>18</sub>H<sub>15</sub>P</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>262.29 g·mol⁻¹ </td></tr> <tr> <td>外观 </td> <td>白色固体 </td></tr> <tr> <td><a href="/wiki/%E5%AF%86%E5%BA%A6" title="密度">密度</a> </td> <td>1.1 </td></tr> <tr> <td><a href="/wiki/%E7%86%94%E7%82%B9" title="熔点">熔点</a> </td> <td>80 °C（176 °F；353 K） </td></tr> <tr> <td><a href="/wiki/%E6%B2%B8%E7%82%B9" title="沸点">沸点</a> </td> <td>377 °C（711 °F；650 K） </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>不可溶 </td></tr> <tr> <td><a href="/wiki/%E6%8A%98%E5%B0%84%E7%8E%87" title="折射率">折光度</a><i>n</i><span style="font-size: 70%;display:inline-block; vertical-align: -0.4em; line-height:1.1em;"><br /><i>D</i></span> </td> <td>1.59；<a href="/wiki/%E4%BB%8B%E9%9B%BB%E4%BF%82%E6%95%B8" class="mw-redirect" title="介電係數">ε<sub>r</sub></a> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">结构 </th></tr> <tr> <td><a href="/wiki/%E5%88%86%E5%AD%90%E7%BB%93%E6%9E%84" title="分子结构">分子构型</a> </td> <td><a href="/wiki/%E4%B8%89%E8%A7%92%E9%94%A5%E5%BD%A2%E5%88%86%E5%AD%90%E6%9E%84%E5%9E%8B" title="三角锥形分子构型">三角锥</a> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">危险性 </th></tr> <tr> <td><a href="/wiki/%E8%AD%A6%E7%A4%BA%E6%80%A7%E8%B3%AA%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8" title="警示性質標準詞列表">警示术语</a> </td> <td>R：<a href="/wiki/%E8%AD%A6%E7%A4%BA%E6%80%A7%E8%B3%AA%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#R20" title="警示性質標準詞列表"><abbr class="abbr" title="R20: 吸入有害">R20</abbr></a>-<a href="/wiki/%E8%AD%A6%E7%A4%BA%E6%80%A7%E8%B3%AA%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#R22" title="警示性質標準詞列表"><abbr class="abbr" title="R22: 吞食有害">R22</abbr></a>-<a href="/wiki/%E8%AD%A6%E7%A4%BA%E6%80%A7%E8%B3%AA%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#R40" title="警示性質標準詞列表"><abbr class="abbr" title="R40: 有限的證據顯示本物質可能致癌">R40</abbr></a>-<a href="/wiki/%E8%AD%A6%E7%A4%BA%E6%80%A7%E8%B3%AA%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#R43" title="警示性質標準詞列表"><abbr class="abbr" title="R43: 皮膚接觸可能導致過敏">R43</abbr></a>-<a href="/wiki/%E8%AD%A6%E7%A4%BA%E6%80%A7%E8%B3%AA%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#R50" title="警示性質標準詞列表"><abbr class="abbr" title="R50: 对水生生物剧毒">R50</abbr></a>-<a href="/wiki/%E8%AD%A6%E7%A4%BA%E6%80%A7%E8%B3%AA%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#R53" title="警示性質標準詞列表"><abbr class="abbr" title="R53: 可能对水体环境产生长期不良影响">R53</abbr></a> </td></tr> <tr> <td><a href="/wiki/%E5%AE%89%E5%85%A8%E5%BB%BA%E8%AD%B0%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8" title="安全建議標準詞列表">安全术语</a> </td> <td>S：<a href="/wiki/%E5%AE%89%E5%85%A8%E5%BB%BA%E8%AD%B0%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#S36" title="安全建議標準詞列表"><abbr class="abbr" title="S36: 穿戴适合的防护服">S36</abbr></a>-<a href="/wiki/%E5%AE%89%E5%85%A8%E5%BB%BA%E8%AD%B0%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#S37" title="安全建議標準詞列表"><abbr class="abbr" title="S37: 穿戴适合的手套">S37</abbr></a>-<a href="/wiki/%E5%AE%89%E5%85%A8%E5%BB%BA%E8%AD%B0%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#S45" title="安全建議標準詞列表"><abbr class="abbr" title="S45: 发生事故或感到不适时立即求医，可能的话出示标签">S45</abbr></a>-<a href="/wiki/%E5%AE%89%E5%85%A8%E5%BB%BA%E8%AD%B0%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#S57" title="安全建議標準詞列表"><abbr class="abbr" title="S57: 适当封存以免污染环境">S57</abbr></a>-<a href="/wiki/%E5%AE%89%E5%85%A8%E5%BB%BA%E8%AD%B0%E6%A8%99%E6%BA%96%E8%A9%9E%E5%88%97%E8%A1%A8#S60" title="安全建議標準詞列表"><abbr class="abbr" title="S60: 该物质及容器必须按危险废物放置">S60</abbr></a> </td></tr> <tr> <td><a href="/wiki/%E5%8C%96%E5%AD%A6%E5%93%81%E5%AE%89%E5%85%A8%E8%AF%B4%E6%98%8E%E4%B9%A6" class="mw-redirect" title="化学品安全说明书">MSDS</a> </td> <td><a rel="nofollow" class="external text" href="http://sciencelab.com/msds.php?msdsId=9925342">ScienceLab.com</a> </td></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>未列明 </td></tr> <tr> <td><a href="/wiki/%E9%97%AA%E7%82%B9" title="闪点">闪点</a> </td> <td>180 °C（356 °F；453 K） </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">相关物质 </th></tr> <tr> <td>相关<a href="/w/index.php?title=%E4%B8%89%E7%BA%A7%E8%86%A6&action=edit&redlink=1" class="new" title="三级膦（页面不存在）">三级膦</a> </td> <td><a href="/wiki/%E4%B8%89%E7%94%B2%E5%9F%BA%E7%A3%B7" class="mw-redirect" title="三甲基磷">三甲基磷</a><br /><a href="/w/index.php?title=%E4%B8%89%E8%8B%AF%E5%9F%BA%E7%A3%B7%E4%B8%89%E9%97%B4%E7%A3%BA%E9%85%B8&action=edit&redlink=1" class="new" title="三苯基磷三间磺酸（页面不存在）">三苯基磷三间磺酸</a><br /><a href="/wiki/%E8%86%A6" title="膦">膦</a> </td></tr> <tr> <td>相关化学品 </td> <td><a href="/wiki/%E4%B8%89%E8%8B%AF%E8%83%BA" title="三苯胺">三苯胺</a><br /><a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E7%A0%B7" title="三苯基砷">三苯基砷</a><br /><a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E6%B0%A7%E5%8C%96%E8%86%A6" title="三苯基氧化膦">三苯基氧化膦</a><br /><a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E7%A1%AB%E5%8C%96%E8%86%A6" title="三苯基硫化膦">三苯基硫化膦</a><br /><a href="/wiki/%E5%9B%9B(%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6)%E9%92%AF" title="四(三苯基膦)钯">Pd(PPh<sub>3</sub>)<sub>4</sub></a><br /><a href="/w/index.php?title=%E4%B8%89%E8%8B%84%E5%9F%BA%E8%86%A6&action=edit&redlink=1" class="new" title="三苄基膦（页面不存在）">三苄基膦</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>三苯基磷</b>，<a href="/wiki/%E5%88%86%E5%AD%90%E5%BC%8F" title="分子式">分子式</a>(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>P，白色<a href="/wiki/%E5%9B%BA%E4%BD%93" title="固体">固体</a>，是<a href="/wiki/%E7%A3%B7%E5%8C%96%E6%B0%AB" class="mw-redirect" title="磷化氫">磷化氫</a>的三苯（<a href="/wiki/%E8%8B%AF" title="苯">苯</a>、<a href="/wiki/%E7%94%B2%E8%8B%AF" title="甲苯">甲苯</a>、<a href="/wiki/%E4%BA%8C%E7%94%B2%E8%8B%AF" title="二甲苯">二甲苯</a>）取代物。主要表现为<a href="/wiki/%E8%BF%98%E5%8E%9F%E6%80%A7" class="mw-redirect" title="还原性">還原性</a>和<a href="/wiki/%E4%BA%B2%E6%A0%B8%E6%80%A7" class="mw-redirect" title="亲核性">親核性</a>。在有機反應中有相當廣泛的應用。 </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="制备、结构与手性"><span id=".E5.88.B6.E5.A4.87.E3.80.81.E7.BB.93.E6.9E.84.E4.B8.8E.E6.89.8B.E6.80.A7"></span>制备、结构与手性</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6&action=edit&section=1" title="编辑章节：制备、结构与手性"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>实验室制备时一般用<a href="/wiki/%E6%A0%BC%E6%B0%8F%E8%AF%95%E5%89%82" title="格氏试剂">格氏试剂</a>与<a href="/wiki/%E4%B8%89%E6%B0%AF%E5%8C%96%E7%A3%B7" title="三氯化磷">三氯化磷</a>作用而得。 </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Ph3Psynthesis_cn.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Ph3Psynthesis_cn.png/500px-Ph3Psynthesis_cn.png" decoding="async" width="500" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Ph3Psynthesis_cn.png/750px-Ph3Psynthesis_cn.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Ph3Psynthesis_cn.png/1000px-Ph3Psynthesis_cn.png 2x" data-file-width="1510" data-file-height="316" /></a></span></dd></dl> <p>工业生产则采用三氯化磷、<a href="/wiki/%E6%B0%AF%E8%8B%AF" title="氯苯">氯苯</a>和<a href="/wiki/%E9%92%A0" title="钠">钠</a>的反应。三苯基膦具有锥形的分子结构。令人惊讶的是三苯基膦是有<a href="/wiki/%E6%89%8B%E6%80%A7" title="手性">手性</a>的分子。因为三个<a href="/wiki/%E8%8B%AF%E7%8E%AF" class="mw-redirect" title="苯环">苯环</a>的<a href="/wiki/%E4%BD%8D%E9%98%BB%E6%95%88%E5%BA%94" title="位阻效应">位阻效应</a>，苯环的实际排布是呈螺旋状的，就像排风扇的三个叶片。而这是个非常典型的手性结构。同时由于三苯基膦具有<a href="/wiki/%E5%89%9B%E6%80%A7" class="mw-redirect" title="剛性">刚性</a>分子结构，比较容易<a href="/wiki/%E7%BB%93%E6%99%B6" title="结晶">结晶</a>。 </p> <div class="mw-heading mw-heading2"><h2 id="氧化和与硫属元素、卤族元素及酸的重要反应"><span id=".E6.B0.A7.E5.8C.96.E5.92.8C.E4.B8.8E.E7.A1.AB.E5.B1.9E.E5.85.83.E7.B4.A0.E3.80.81.E5.8D.A4.E6.97.8F.E5.85.83.E7.B4.A0.E5.8F.8A.E9.85.B8.E7.9A.84.E9.87.8D.E8.A6.81.E5.8F.8D.E5.BA.94"></span>氧化和与硫属元素、卤族元素及酸的重要反应</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6&action=edit&section=2" title="编辑章节：氧化和与硫属元素、卤族元素及酸的重要反应"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>三苯基膦在空气中被氧化为<a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E6%B0%A7%E5%8C%96%E8%86%A6" title="三苯基氧化膦">三苯基氧化膦</a>的反应很缓慢： </p> <dl><dd>2 PPh<sub>3</sub> + O<sub>2</sub> → 2 OPPh<sub>3</sub></dd></dl> <p>但是久置的三苯基膦依然需要提纯。通常采用的方法是将含有三苯基氧化膦杂质的样品在热的<a href="/wiki/%E4%B9%99%E9%86%87" title="乙醇">乙醇</a>或<a href="/wiki/%E5%BC%82%E4%B8%99%E9%86%87" class="mw-redirect" title="异丙醇">异丙醇</a>中溶解，然后对三苯基膦进行<a href="/wiki/%E9%87%8D%E7%BB%93%E6%99%B6" title="重结晶">重结晶</a>。由于三苯基氧化膦是极性比三苯基膦更大的分子，所以会留在溶液中，从而达到分离的目的。虽然在空气中的氧化进行缓慢，但其实三苯基膦还原性能较好，可以将<a href="/wiki/%E8%BF%87%E6%B0%A7%E5%8C%96%E7%89%A9" title="过氧化物">过氧化物</a>还原，同时保持其构型： </p> <dl><dd>PPh<sub>3</sub> + RO<sub>2</sub>H → OPPh<sub>3</sub> + ROH (R = 烃基)</dd></dl> <p>三苯基膦还能脱去<a href="/wiki/%E5%A4%9A%E7%A1%AB%E5%8C%96%E7%89%A9" title="多硫化物">多硫化物</a>和<a href="/wiki/%E7%8E%AF%E7%A1%AB%E5%8C%96%E7%89%A9" title="环硫化物">环硫化物</a>中的“零价硫”，甚至可以吸收单质<a href="/wiki/%E7%A1%AB" title="硫">硫</a>。但是与<a href="/wiki/%E7%A1%AB%E9%86%87" title="硫醇">硫醇</a>、<a href="/wiki/%E7%A1%AB%E9%86%9A" title="硫醚">硫醚</a>等化合物却不能反应。三苯基膦转化为<a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E7%A1%AB%E5%8C%96%E8%86%A6" title="三苯基硫化膦">三苯基硫化膦</a>（Ph<sub>3</sub>PS）。这个性质可以用于测定诸如硫化<a href="/wiki/%E6%A9%A1%E8%83%B6" class="mw-redirect" title="橡胶">橡胶</a>等物质中的“零价硫”。三苯基膦与<a href="/w/index.php?title=%E7%BA%A2%E7%A1%92&action=edit&redlink=1" class="new" title="红硒（页面不存在）">红硒</a>（又称“<a href="/w/index.php?title=%CE%91%E7%A1%92&action=edit&redlink=1" class="new" title="Α硒（页面不存在）">α硒</a>”，<a href="/wiki/%E5%8D%95%E6%96%9C" class="mw-redirect" title="单斜">单斜</a>）可以很容易地反应得到<a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E7%A1%92%E5%8C%96%E8%86%A6" title="三苯基硒化膦">三苯基硒化膦</a>（Ph<sub>3</sub>PSe）。<style data-mw-deduplicate="TemplateStyles:r83946278">.mw-parser-output .template-facttext{background-color:var(--background-color-neutral,#eaecf0);color:inherit;margin:-.3em 0;padding:.3em 0}</style><mark class="template-facttext" title="需要提供文献来源">同样的“零价<a href="/wiki/%E7%A1%92" title="硒">硒</a>”来源还有<a href="/wiki/%E7%A1%92%E6%B0%B0" title="硒氰">硒氰</a>根离子（SeCN<sup>-</sup>）。</mark><sup class="noprint Template-Fact"><a href="/wiki/Wikipedia:%E5%88%97%E6%98%8E%E6%9D%A5%E6%BA%90" title="Wikipedia:列明来源"><span style="white-space: nowrap;" title="来源请求。">[來源請求]</span></a></sup> 三苯基膦也可以与<a href="/wiki/%E7%A2%B2" title="碲">碲</a>生成加合物，但主要产物是(Ph<sub>3</sub>P)<sub>2</sub>Te而不同于前面的形式。 </p><p><a href="/wiki/%E5%8F%A0%E6%B0%AE%E5%8C%96%E5%90%88%E7%89%A9" title="叠氮化合物">叠氮化合物</a>与三苯基膦反应生成<a href="/wiki/%E4%BA%9A%E8%83%BA" title="亚胺">亚胺</a>的类似物，例如<a href="/wiki/Staudinger%E5%8F%8D%E5%BA%94" class="mw-redirect" title="Staudinger反应">Staudinger反应</a>： </p> <dl><dd>PPh<sub>3</sub> + PhN<sub>3</sub> → PhNPPh<sub>3</sub> + N<sub>2</sub></dd></dl> <p>对产物进行<a href="/wiki/%E6%B0%B4%E8%A7%A3" title="水解">水解</a>可以得到亚胺： </p> <dl><dd>PPh<sub>3</sub> + RN<sub>3</sub> + H<sub>2</sub>O → OPPh<sub>3</sub> + N<sub>2</sub> + RNH<sub>2</sub></dd></dl> <p><a href="/wiki/%E6%B0%AF%E6%B0%94" title="氯气">氯气</a>可以与三苯基膦<a href="/wiki/%E5%8C%96%E5%90%88" class="mw-redirect" title="化合">化合</a>生成<a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E4%BA%8C%E6%B0%AF%E5%8C%96%E8%86%A6" title="三苯基二氯化膦">三苯基二氯化膦</a>（([PPh<sub>3</sub>Cl]Cl)）。它是一种易吸湿的<a href="/wiki/%E7%A6%BB%E5%AD%90%E6%99%B6%E4%BD%93" title="离子晶体">离子晶体</a>，常用于将<a href="/wiki/%E9%86%87" title="醇">醇</a>转化为<a href="/wiki/%E5%8D%A4%E4%BB%A3%E7%83%83" class="mw-redirect" title="卤代烃">卤代烃</a>。 </p><p>三苯基膦是一种很弱的<a href="/wiki/%E7%A2%B1" title="碱">碱</a>，但依然可以与强<a href="/wiki/%E9%85%B8" title="酸">酸</a>如<a href="/wiki/%E6%B0%A2%E6%BA%B4%E9%85%B8" title="氢溴酸">氢溴酸</a>生成稳定的<a href="/wiki/%E7%9B%90" class="mw-redirect" title="盐">盐</a>。它和<a href="/wiki/%E4%BA%8C%E6%B0%9F%E6%BA%B4%E4%B9%99%E9%85%B8%E9%92%BE" title="二氟溴乙酸钾">二氟溴乙酸钾</a>反应，可以得到三苯基𬭸基二氟乙酸内盐。<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> <div class="mw-heading mw-heading2"><h2 id="应用"><span id=".E5.BA.94.E7.94.A8"></span>应用</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6&action=edit&section=3" title="编辑章节：应用"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>臭氧化反应还原剂：参见<a href="/wiki/%E8%87%AD%E6%B0%A7%E5%8C%96%E5%8F%8D%E5%BA%94" title="臭氧化反应">臭氧化反应</a>。</li> <li>光延反应试剂：参见<a href="/wiki/%E5%85%89%E5%BB%B6%E5%8F%8D%E5%BA%94" title="光延反应">光延反应</a>。</li> <li>作为一些过渡金属催化剂中的<a href="/wiki/%E9%85%8D%E4%BD%93" class="mw-redirect" title="配体">配体</a>：参见<a href="/wiki/%E5%9B%9B(%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6)%E9%92%AF" title="四(三苯基膦)钯">四(三苯基膦)钯</a>、<a href="/wiki/%E5%A8%81%E5%B0%94%E9%87%91%E6%A3%AE%E5%82%AC%E5%8C%96%E5%89%82" title="威尔金森催化剂">威尔金森催化剂</a></li> <li>叠氮化物还原剂：与水配合可以把有机<a href="/wiki/%E5%8F%A0%E6%B0%AE%E5%8C%96%E7%89%A9" class="mw-redirect" title="叠氮化物">叠氮化物</a>还原为<a href="/wiki/%E8%83%BA" title="胺">胺</a>。</li></ul> <dl><dd>RN<sub>3</sub> + Ph<sub>3</sub>P + H<sub>2</sub>O = RNH<sub>2</sub> + Ph<sub>3</sub>PO + N<sub>2</sub></dd></dl> <ul><li>炔酸酯变二烯反应<a href="/wiki/%E5%82%AC%E5%8C%96%E5%89%82" title="催化剂">催化剂</a>：α,β-炔酸酯在三苯基膦<a href="/wiki/%E5%82%AC%E5%8C%96" title="催化">催化</a>下重排为共轭二烯酸酯(山梨酸酯)：</li></ul> <dl><dd><span typeof="mw:File"><a href="/wiki/File:PH3P_cat_cn.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/PH3P_cat_cn.png/450px-PH3P_cat_cn.png" decoding="async" width="450" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/PH3P_cat_cn.png/675px-PH3P_cat_cn.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/PH3P_cat_cn.png/900px-PH3P_cat_cn.png 2x" data-file-width="1118" data-file-height="186" /></a></span></dd></dl> <ul><li>用于合成<a href="/wiki/%E7%BB%B4%E8%92%82%E5%B8%8C%E5%8F%8D%E5%BA%94" title="维蒂希反应">维蒂希反应</a>中的<a href="/wiki/%E7%A3%B7%E5%8F%B6%E7%AB%8B%E5%BE%B7" class="mw-redirect" title="磷叶立德">磷叶立德</a>：</li></ul> <dl><dd>Ph<sub>3</sub>P + CH<sub>3</sub>Br → Ph<sub>3</sub>P<sup>+</sup>-CH<sub>3</sub>·Br<sup>−</sup> -(干燥乙醚,PhLi)→ Ph<sub>3</sub>P<sup>+</sup>-CH<sub>2</sub><sup>−</sup></dd></dl> <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=%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6&action=edit&section=4" title="编辑章节：参考文献"><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">Niklas B. Heine, Armido Studer. <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/10.1021/acs.orglett.7b02109">Radical Difluoromethylation of Thiols with (Difluoromethyl)triphenylphosphonium Bromide</a>. Organic Letters. 2017-08-04, <b>19</b> (15): 4150–4153 <span class="reference-accessdate"> [<span class="nowrap">2021-10-20</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%2Facs.orglett.7b02109"><span title="數位物件識別號">doi:10.1021/acs.orglett.7b02109</span></a>. （原始内容<a rel="nofollow" class="external text" href="https://web.archive.org/web/20211023111714/https://pubs.acs.org/doi/10.1021/acs.orglett.7b02109">存档</a>于2021-10-23） <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 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<td>He </td></tr> <tr style="background-color:mistyrose;vertical-align:top"> <td><a href="/wiki/%E8%8B%AF%E5%9F%BA%E9%94%82" title="苯基锂">C<sub>6</sub>H<sub>5</sub>Li</a> </td> <td>Be </td> <td><a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E7%A1%BC" title="三苯基硼">(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>B</a> </td> <td><a href="/wiki/%E5%9B%9B%E8%8B%AF%E7%94%B2%E7%83%B7" title="四苯甲烷">(C<sub>6</sub>H<sub>5</sub>)<sub>4</sub>C</a> </td> <td><a href="/wiki/%E4%B8%89%E8%8B%AF%E8%83%BA" title="三苯胺">(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>N</a> </td> <td><a href="/wiki/%E4%BA%8C%E8%8B%AF%E9%86%9A" title="二苯醚">(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>O</a> </td> <td><a href="/wiki/%E6%B0%9F%E8%8B%AF" title="氟苯">C<sub>6</sub>H<sub>5</sub>F</a> </td> <td>Ne </td></tr> <tr style="background-color:mistyrose;vertical-align:top"> <td><a href="/wiki/%E8%8B%AF%E5%9F%BA%E9%92%A0" title="苯基钠">C<sub>6</sub>H<sub>5</sub>Na</a> </td> <td><a href="/wiki/%E4%BA%8C%E8%8B%AF%E5%9F%BA%E9%95%81" title="二苯基镁">(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>Mg</a> </td> <td><a href="/w/index.php?title=%E4%B8%89%E8%8B%AF%E5%9F%BA%E9%93%9D&action=edit&redlink=1" class="new" title="三苯基铝（页面不存在）">(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>Al</a> </td> <td><a href="/wiki/%E5%9B%9B%E8%8B%AF%E5%9F%BA%E7%A1%85" title="四苯基硅">(C<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />6</span>H<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />5</span>)<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />4</span>Si</a> </td> <td><a class="mw-selflink selflink">(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>P</a><br /><a href="/wiki/%E4%BA%94%E8%8B%AF%E5%9F%BA%E7%A3%B7" title="五苯基磷">(C<sub>6</sub>H<sub>5</sub>)<sub>5</sub>P</a> </td> <td><a href="/wiki/%E8%8B%AF%E7%A1%AB%E9%86%9A" title="苯硫醚">(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>S</a><br /><a href="/wiki/%E4%BA%8C%E8%8B%AF%E5%9F%BA%E4%BA%8C%E7%A1%AB%E9%86%9A" title="二苯基二硫醚"><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>S)<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 />2</span></span></a> </td> <td><a href="/wiki/%E6%B0%AF%E8%8B%AF" title="氯苯">C<sub>6</sub>H<sub>5</sub>Cl</a> </td> <td>Ar </td></tr> <tr style="background-color:mistyrose;vertical-align:top"> <td>K </td> <td>Ca </td> <td>Sc </td> <td>Ti </td> <td>V </td> <td>Cr </td> <td>Mn </td> <td>Fe </td> <td>Co </td> <td>Ni </td> <td><a href="/wiki/%E8%8B%AF%E5%9F%BA%E9%93%9C" title="苯基铜">C<sub>6</sub>H<sub>5</sub>Cu</a> </td> <td><a href="/wiki/%E4%BA%8C%E8%8B%AF%E5%9F%BA%E9%94%8C" title="二苯基锌">(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>Zn</a> </td> <td><a href="/w/index.php?title=%E4%B8%89%E8%8B%AF%E5%9F%BA%E9%95%93&action=edit&redlink=1" class="new" title="三苯基镓（页面不存在）">(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>Ga</a> </td> <td><a href="/wiki/%E5%9B%9B%E8%8B%AF%E5%9F%BA%E9%94%97" title="四苯基锗">(C<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />6</span>H<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />5</span>)<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />4</span>Ge</a> </td> <td><a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E7%A0%B7" title="三苯基砷">(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>As</a> </td> <td><a href="/wiki/%E4%BA%8C%E8%8B%AF%E5%9F%BA%E4%BA%8C%E7%A1%92%E9%86%9A" title="二苯基二硒醚"><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>Se)<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 />2</span></span></a> </td> <td><a href="/wiki/%E6%BA%B4%E8%8B%AF" title="溴苯">C<sub>6</sub>H<sub>5</sub>Br</a> </td> <td>Kr </td></tr> <tr style="background-color:mistyrose;vertical-align:top"> <td>Rb </td> <td>Sr </td> <td>Y </td> <td>Zr </td> <td>Nb </td> <td>Mo </td> <td>Tc </td> <td>Ru </td> <td>Rh </td> <td>Pd </td> <td><a href="/wiki/%E8%8B%AF%E5%9F%BA%E9%93%B6" title="苯基银">C<sub>6</sub>H<sub>5</sub>Ag</a> </td> <td><a href="/w/index.php?title=%E4%BA%8C%E8%8B%AF%E5%9F%BA%E9%95%89&action=edit&redlink=1" class="new" title="二苯基镉（页面不存在）">(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>Cd</a> </td> <td><a href="/w/index.php?title=%E4%B8%89%E8%8B%AF%E5%9F%BA%E9%93%9F&action=edit&redlink=1" class="new" title="三苯基铟（页面不存在）">(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>In</a> </td> <td><a href="/wiki/%E4%BA%8C%E8%8B%AF%E5%9F%BA%E9%94%A1" title="二苯基锡">(C<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />6</span>H<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />5</span>)<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />2</span>Sn</a><br /><a href="/wiki/%E5%9B%9B%E8%8B%AF%E5%9F%BA%E9%94%A1" title="四苯基锡">(C<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />6</span>H<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />5</span>)<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />4</span>Sn</a> </td> <td><a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E4%8F%B2" title="三苯基䏲">(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>Sb</a><br /><a href="/wiki/%E4%BA%94%E8%8B%AF%E5%9F%BA%E9%94%91" title="五苯基锑">(C<sub>6</sub>H<sub>5</sub>)<sub>5</sub>Sb</a> </td> <td><a href="/wiki/%E4%BA%8C%E8%8B%AF%E5%9F%BA%E4%BA%8C%E7%A2%B2" title="二苯基二碲"><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>Te)<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 />2</span></span></a> </td> <td><a href="/wiki/%E7%A2%98%E8%8B%AF" title="碘苯">C<sub>6</sub>H<sub>5</sub>I</a> </td> <td>Xe </td></tr> <tr style="background-color:mistyrose;vertical-align:top"> <td>Cs </td> <td>Ba </td> <td style="background-color:white;border:none"><span title="镧系元素" style="font-family: Courier, monospace;">镧系</span> </td> <td>Hf </td> <td>Ta </td> <td>W </td> <td>Re </td> <td>Os </td> <td>Ir </td> <td>Pt </td> <td>Au </td> <td><a href="/wiki/%E4%BA%8C%E8%8B%AF%E5%9F%BA%E6%B1%9E" title="二苯基汞">(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>Hg</a> </td> <td><a href="/w/index.php?title=%E4%B8%89%E8%8B%AF%E5%9F%BA%E9%93%8A&action=edit&redlink=1" class="new" title="三苯基铊（页面不存在）">(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>Tl</a> </td> <td><a href="/w/index.php?title=%E4%BA%8C%E8%8B%AF%E5%9F%BA%E9%93%85&action=edit&redlink=1" class="new" title="二苯基铅（页面不存在）">(C<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />6</span>H<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />5</span>)<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />2</span>Pb</a><br /><a href="/wiki/%E5%9B%9B%E8%8B%AF%E5%9F%BA%E9%93%85" title="四苯基铅">(C<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />6</span>H<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />5</span>)<span style="display:inline-block; margin-bottom:-0.3em; vertical-align:-0.4em; line-height:1.2em; font-size:70%; text-align:left;"><br />4</span>Pb</a> </td> <td><a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E9%93%8B" title="三苯基铋"><span class="chemf nowrap">Bi(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>)<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 />3</span></span></a><br /><a href="/wiki/%E4%BA%94%E8%8B%AF%E5%9F%BA%E9%93%8B" title="五苯基铋"><span class="chemf nowrap">Bi(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>)<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></span></a> </td> <td>Po </td> <td>At </td> <td>Rn </td></tr> <tr style="background-color:mistyrose;vertical-align:top"> <td>Fr </td> <td>Ra </td> <td style="background-color:white;border:none"><span title="锕系元素" style="font-family: Courier, monospace;">锕系</span> </td> <td>Rf </td> <td>Db </td> <td>Sg </td> <td>Bh </td> <td>Hs </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="background-color:white;border:none" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="1"> </td> <td style="background-color:white;border:none">↓ </td> <td style="background-color:white;border:none" colspan="14"> </td> <td style="background-color:white;border:none" rowspan="3"> </td></tr> <tr style="background-color:mistyrose;vertical-align:top"> <td style="background-color:white;border:none"><span title="镧系元素" style="font-family: Courier, monospace;">镧系</span> </td> <td>La </td> <td>Ce </td> <td>Pr </td> <td>Nd </td> <td>Pm </td> <td>Sm </td> <td>Eu </td> <td>Gd </td> <td>Tb </td> <td>Dy </td> <td>Ho </td> <td>Er </td> <td>Tm </td> <td>Yb </td> <td>Lu </td></tr> <tr style="background-color:mistyrose;vertical-align:top"> <td style="background-color:white;border:none"><span title="锕系元素" style="font-family: Courier, monospace;">锕系</span> </td> <td>Ac </td> <td>Th </td> <td>Pa </td> <td>U </td> <td>Np </td> <td>Pu </td> <td>Am </td> <td>Cm </td> <td>Bk </td> <td>Cf </td> <td>Es </td> <td>Fm </td> <td>Md </td> <td>No </td> <td>Lr </td></tr></tbody></table> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1&useformat=desktop" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">检索自“<a dir="ltr" href="https://zh.wikipedia.org/w/index.php?title=三苯基膦&oldid=78626515">https://zh.wikipedia.org/w/index.php?title=三苯基膦&oldid=78626515</a>”</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Special:%E9%A1%B5%E9%9D%A2%E5%88%86%E7%B1%BB" title="Special:页面分类">分类</a>：<ul><li><a href="/wiki/Category:%E8%8B%AF%E5%9F%BA%E5%8C%96%E5%90%88%E7%89%A9" title="Category:苯基化合物">苯基化合物</a></li><li><a href="/wiki/Category:%E5%8F%94%E8%86%A6" title="Category:叔膦">叔膦</a></li></ul></div><div id="mw-hidden-catlinks" 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