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1-氯丙烷 - 维基百科,自由的百科全书
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class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=zh.wikipedia.org&uselang=zh"><span>资助维基百科</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:%E5%88%9B%E5%BB%BA%E8%B4%A6%E6%88%B7&returnto=1-%E6%B0%AF%E4%B8%99%E7%83%B7" 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=1-%E6%B0%AF%E4%B8%99%E7%83%B7" 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"><!-- CentralNotice --></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-製備" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#製備"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>製備</span> </div> </a> <ul id="toc-製備-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-反應" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#反應"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>反應</span> </div> </a> <button aria-controls="toc-反應-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>开关反應子章节</span> </button> <ul id="toc-反應-sublist" class="vector-toc-list"> <li id="toc-異構化" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#異構化"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>異構化</span> </div> </a> <ul id="toc-異構化-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-雙分子親核取代反應" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#雙分子親核取代反應"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>雙分子親核取代反應</span> </div> </a> <ul id="toc-雙分子親核取代反應-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-與金屬的反應" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#與金屬的反應"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>與金屬的反應</span> </div> </a> <ul id="toc-與金屬的反應-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-用途" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#用途"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>用途</span> </div> </a> <ul id="toc-用途-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-參考資料" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#參考資料"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>參考資料</span> </div> </a> <ul id="toc-參考資料-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" title="目录" > <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">1-氯丙烷</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。17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-17" 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">17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-az mw-list-item"><a href="https://az.wikipedia.org/wiki/1-Xlorpropan" title="1-Xlorpropan – 阿塞拜疆语" lang="az" hreflang="az" data-title="1-Xlorpropan" 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/%D8%A7%D9%86%E2%80%93%D9%BE%D8%B1%D9%88%D9%BE%DB%8C%D9%84_%DA%A9%D9%88%D9%84%D9%88%D8%B1%DB%8C%D8%AF" title="ان–پروپیل کولورید – South Azerbaijani" lang="azb" hreflang="azb" data-title="ان–پروپیل کولورید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/1-Chlorpropan" title="1-Chlorpropan – 德语" lang="de" hreflang="de" data-title="1-Chlorpropan" 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/1-%CF%87%CE%BB%CF%89%CF%81%CE%BF%CF%80%CF%81%CE%BF%CF%80%CE%AC%CE%BD%CE%B9%CE%BF" title="1-χλωροπροπάνιο – 希腊语" lang="el" hreflang="el" data-title="1-χλωροπροπάνιο" 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/N-Propyl_chloride" title="N-Propyl chloride – 英语" lang="en" hreflang="en" data-title="N-Propyl chloride" 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/Propila_klorido" title="Propila klorido – 世界语" lang="eo" hreflang="eo" data-title="Propila klorido" 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-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D9%86%E2%80%93%D9%BE%D8%B1%D9%88%D9%BE%DB%8C%D9%84_%DA%A9%D9%84%D8%B1%DB%8C%D8%AF" title="ان–پروپیل کلرید – 波斯语" lang="fa" hreflang="fa" data-title="ان–پروپیل کلرید" 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/Klooripropaani" title="Klooripropaani – 芬兰语" lang="fi" hreflang="fi" data-title="Klooripropaani" 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-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/1-Kl%C3%B3rprop%C3%A1n" title="1-Klórpropán – 匈牙利语" lang="hu" hreflang="hu" data-title="1-Klórpropán" 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-it mw-list-item"><a href="https://it.wikipedia.org/wiki/1-cloropropano" title="1-cloropropano – 意大利语" lang="it" hreflang="it" data-title="1-cloropropano" 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/1-%E3%82%AF%E3%83%AD%E3%83%AD%E3%83%97%E3%83%AD%E3%83%91%E3%83%B3" title="1-クロロプロパン – 日语" lang="ja" hreflang="ja" data-title="1-クロロプロパン" 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/1-chloorpropaan" title="1-chloorpropaan – 荷兰语" lang="nl" hreflang="nl" data-title="1-chloorpropaan" 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/Cloreto_de_n-propila" title="Cloreto de n-propila – 葡萄牙语" lang="pt" hreflang="pt" data-title="Cloreto de n-propila" 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%A5%D0%BB%D0%BE%D1%80%D0%BF%D1%80%D0%BE%D0%BF%D0%B0%D0%BD" title="Хлорпропан – 俄语" lang="ru" hreflang="ru" data-title="Хлорпропан" 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/N-Propil_hlorid" title="N-Propil hlorid – 塞尔维亚-克罗地亚语" lang="sh" hreflang="sh" data-title="N-Propil hlorid" 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/N-Propil_hlorid" title="N-Propil hlorid – 塞尔维亚语" lang="sr" hreflang="sr" data-title="N-Propil hlorid" 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/1-%E0%AE%AA%E0%AF%81%E0%AE%B0%E0%AF%8B%E0%AE%AA%E0%AF%8D%E0%AE%AA%E0%AF%88%E0%AE%B2%E0%AF%8D_%E0%AE%95%E0%AF%81%E0%AE%B3%E0%AF%8B%E0%AE%B0%E0%AF%88%E0%AE%9F%E0%AF%81" title="1-புரோப்பைல் குளோரைடு – 泰米尔语" lang="ta" hreflang="ta" data-title="1-புரோப்பைல் குளோரைடு" data-language-autonym="தமிழ்" data-language-local-name="泰米尔语" class="interlanguage-link-target"><span>தமிழ்</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/Q161612#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 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mw-portlet mw-portlet-electronpdfservice-sidebar-portlet-heading" > <div class="vector-menu-heading"> 打印/导出 </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="electron-print_pdf" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=1-%E6%B0%AF%E4%B8%99%E7%83%B7&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:1-Chloropropane" hreflang="en"><span>维基共享资源</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;"><i>n</i>-丙基氯 </th></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><a href="/wiki/File:N-propylChloride.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/N-propylChloride.png/200px-N-propylChloride.png" decoding="async" width="200" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/N-propylChloride.png/300px-N-propylChloride.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2f/N-propylChloride.png/400px-N-propylChloride.png 2x" data-file-width="1347" data-file-height="804" /></a></span> </td></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><a href="/wiki/File:1-chloorpropaan.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/1-chloorpropaan.png/150px-1-chloorpropaan.png" decoding="async" width="150" height="42" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/1-chloorpropaan.png/225px-1-chloorpropaan.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/28/1-chloorpropaan.png/300px-1-chloorpropaan.png 2x" data-file-width="381" data-file-height="106" /></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 />1-chloropropane、1-氯丙烷 </td></tr> <tr> <td>别名 </td> <td>氯丙烷<br />正丙基氯<br />丙基氯 </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=540-54-5">540-54-5</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/10899">10899</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/10437">10437</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">ClCCC</span></li></ul> </div></div> </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>3</sub>H<sub>7</sub>Cl</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>78.54 g·mol⁻¹ </td></tr> <tr> <td>外观 </td> <td>无色液体 </td></tr> <tr> <td><a href="/wiki/%E5%AF%86%E5%BA%A6" title="密度">密度</a> </td> <td>0.890 g·cm<sup>−3</sup><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> </td></tr> <tr> <td><a href="/wiki/%E7%86%94%E7%82%B9" title="熔点">熔点</a> </td> <td>−122.8 °C(150.3 K)<sup id="cite_ref-TJ_2-0" class="reference"><a href="#cite_note-TJ-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/%E6%B2%B8%E7%82%B9" title="沸点">沸点</a> </td> <td>46.6 °C(319.8 K)<sup id="cite_ref-TJ_2-1" class="reference"><a href="#cite_note-TJ-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </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>0.27 g/100 ml(20 °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/%E4%B9%99%E9%86%87" title="乙醇">乙醇</a>) </td> <td><a href="/wiki/%E6%B7%B7%E6%BA%B6" title="混溶">混溶</a> </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/%E4%B9%99%E9%86%9A" title="乙醚">乙醚</a>) </td> <td><a href="/wiki/%E6%B7%B7%E6%BA%B6" title="混溶">混溶</a> </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>1.3886 </td></tr> <tr> <td><a href="/wiki/%E9%BB%8F%E5%BA%A6" title="黏度">黏度</a> </td> <td>4.416 c<a href="/wiki/Poise_(unit)" class="mw-redirect" title="Poise (unit)">P</a> at 0 °C<br />3.589 c<a href="/wiki/Poise_(unit)" class="mw-redirect" title="Poise (unit)">P</a> at 20 °C </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#R11" title="警示性質標準詞列表"><abbr class="abbr" title="R11: 高度易燃">R11</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#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#R21" title="警示性質標準詞列表"><abbr class="abbr" title="R21: 触摸有害">R21</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> </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#S9" title="安全建議標準詞列表"><abbr class="abbr" title="S9: 容器必须储放于通风良好的地方">S9</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#S16" title="安全建議標準詞列表"><abbr class="abbr" title="S16: 远离燃点 - 禁烟">S16</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#S26" title="安全建議標準詞列表"><abbr class="abbr" title="S26: 接触眼睛后立即用大量清水冲洗并求医">S26</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#S29" title="安全建議標準詞列表"><abbr class="abbr" title="S29: 禁止排入下水道">S29</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#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> </td></tr> <tr> <td>主要危害 </td> <td>液體及蒸氣極度易燃。 蒸氣可能引起閃火。吸食有害。 皮膚吸收可能有害。 影響中樞神經系統。 刺激皮膚、眼睛,和呼吸道。 </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3級。在通常溫度下可被點燃的固體或液體(如汽油)。閃點在23 - 38°C"><b>3</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2級。高濃度或持續性暴露可能導致暫時失去行為能力或可能造成持續性傷害(如氯仿)。"><b>2</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;"> </div> </div> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">相关物质 </th></tr> <tr> <td>相关化合物 </td> <td><a href="/wiki/%E6%B0%AF%E4%B9%99%E7%83%B7" title="氯乙烷">氯乙烷</a><br /><a href="/wiki/2-%E6%B0%AF%E4%B8%99%E7%83%B7" title="2-氯丙烷">2-氯丙烷</a><br /><a href="/wiki/%E5%8F%94%E4%B8%81%E5%9F%BA%E6%B0%AF" title="叔丁基氯">叔丁基氯</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>1-氯丙烷</b>,又稱<b>正丙基氯</b>,化學式是<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 {\ce {C3H7Cl}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>7</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>Cl</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {C3H7Cl}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/bea69fe0a2f1e1db6668c733cd91beed6e647e2f" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:7.855ex; height:2.843ex;" alt="{\displaystyle {\ce {C3H7Cl}}}" /></span>,屬於<a href="/wiki/%E6%9C%89%E6%9C%BA%E5%8C%96%E5%90%88%E7%89%A9" title="有机化合物">有機化合物</a>,是<a href="/wiki/%E6%B0%AF%E4%BB%A3%E7%83%B7" title="氯代烷">氯代烷</a>的一種。它是種無色、易燃的液體<sup id="cite_ref-:1_3-0" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>,有<a href="/wiki/%E6%B0%AF%E4%BB%BF" title="氯仿">氯仿</a>的氣味。它的密度比水更小<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>,而且微溶於水。 </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="製備"><span id=".E8.A3.BD.E5.82.99"></span>製備</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1-%E6%B0%AF%E4%B8%99%E7%83%B7&action=edit&section=1" title="编辑章节:製備"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>1-氯丙烷可由<a href="/wiki/1-%E4%B8%99%E9%86%87" title="1-丙醇">正丙醇</a>和<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>、<a href="/wiki/%E4%BA%94%E6%B0%AF%E5%8C%96%E7%A3%B7" title="五氯化磷">五氯化磷</a>或<a href="/wiki/%E7%9B%90%E9%85%B8" title="盐酸">鹽酸</a>製備而成。<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>在<a href="/wiki/%E4%B8%89%E8%8B%AF%E5%9F%BA%E8%86%A6" title="三苯基膦">三苯基膦</a>的存在下,正丙醇也可以和<a href="/wiki/%E5%9B%9B%E6%B0%AF%E5%8C%96%E7%A2%B3" title="四氯化碳">四氯化碳</a>反应,得到1-氯丙烷。<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>此外,<a href="/wiki/%E4%B8%89%E7%94%B2%E5%9F%BA%E6%B0%AF%E7%A1%85%E7%83%B7" title="三甲基氯硅烷">三甲基氯硅烷</a>也可作为氯化试剂。<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>在<a href="/wiki/%E4%B8%99%E7%83%AF" title="丙烯">丙烯</a>的<a href="/wiki/%E9%B9%B5%E6%B0%AB%E5%8C%96%E4%BD%9C%E7%94%A8" title="鹵氫化作用">鹵氫化反應</a>裏,根據<a href="/wiki/%E9%A9%AC%E6%B0%8F%E8%A7%84%E5%88%99" class="mw-redirect" title="马氏规则">馬氏規則</a>,1-氯丙烷只是副產品,而<a href="/wiki/2-%E6%B0%AF%E4%B8%99%E7%83%B7" title="2-氯丙烷">2-氯丙烷</a>才是主要的生成物。<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>這是因為反應跟從<a href="/wiki/%E4%BA%B2%E7%94%B5%E5%8A%A0%E6%88%90%E5%8F%8D%E5%BA%94" title="亲电加成反应">親電加成</a>的<a href="/wiki/%E5%8F%8D%E5%BA%94%E6%9C%BA%E7%90%86" title="反应机理">反應機理</a>,反應中途涉及到<a href="/wiki/%E7%A2%B3%E6%AD%A3%E7%A6%BB%E5%AD%90" title="碳正离子">碳陽離子</a>,而二級碳陽離子比一級碳陽離子更為穩定。因此這反應一般不會用來製備1-氯丙烷。 </p><p>此物也可由過量的<a href="/wiki/%E4%B8%99%E7%83%B7" title="丙烷">丙烷</a>與<a href="/wiki/%E6%B0%AF%E6%B0%94" title="氯气">氯氣</a>在紫外光或陽光照射下反應制得。但在這<a href="/wiki/%E8%87%AA%E7%94%B1%E5%9F%BA%E5%8F%96%E4%BB%A3%E5%8F%8D%E6%87%89" title="自由基取代反應">自由基取代反應</a>中,產物通常是多個<a href="/wiki/%E6%B0%AF%E4%BB%A3%E7%83%B7" title="氯代烷">氯代烷</a>的<a href="/wiki/%E6%B7%B7%E5%90%88%E7%89%A9" title="混合物">混合物</a>。<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="反應"><span id=".E5.8F.8D.E6.87.89"></span>反應</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1-%E6%B0%AF%E4%B8%99%E7%83%B7&action=edit&section=2" title="编辑章节:反應"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="異構化"><span id=".E7.95.B0.E6.A7.8B.E5.8C.96"></span>異構化</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1-%E6%B0%AF%E4%B8%99%E7%83%B7&action=edit&section=3" title="编辑章节:異構化"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>在<a href="/wiki/%E4%B8%89%E6%B0%AF%E5%8C%96%E9%93%9D" class="mw-redirect" title="三氯化铝">三氯化鋁</a>存在之下,1-氯丙烷會<a href="/wiki/%E5%BC%82%E6%9E%84%E5%8C%96%E5%8F%8D%E5%BA%94" title="异构化反应">異構化</a>,變為它的<a href="/wiki/%E5%90%8C%E5%88%86%E7%95%B0%E6%A7%8B" title="同分異構">位置異構體</a><a href="/wiki/2-%E6%B0%AF%E4%B8%99%E7%83%B7" title="2-氯丙烷">2-氯丙烷</a>。加熱到約攝氏四百度時,在<a href="/wiki/%E6%B0%AF%E5%8C%96%E9%8B%87" title="氯化鋇">氯化鋇</a>的存在下1-氯丙烷發生反應,生成2-氯丙烷和<a href="/wiki/%E4%B8%99%E7%83%AF" title="丙烯">丙烯</a>。<sup id="cite_ref-:0_10-0" class="reference"><a href="#cite_note-:0-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="雙分子親核取代反應"><span id=".E9.9B.99.E5.88.86.E5.AD.90.E8.A6.AA.E6.A0.B8.E5.8F.96.E4.BB.A3.E5.8F.8D.E6.87.89"></span>雙分子親核取代反應</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1-%E6%B0%AF%E4%B8%99%E7%83%B7&action=edit&section=4" title="编辑章节:雙分子親核取代反應"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>由於1-氯丙烷屬於一級<a href="/wiki/%E6%B0%AF%E4%BB%A3%E7%83%B7" title="氯代烷">氯代烷</a>,<a href="/wiki/%E4%BD%8D%E9%98%BB%E6%95%88%E5%BA%94" title="位阻效应">位阻效應</a>較小,而且一級<a href="/wiki/%E7%A2%B3%E6%AD%A3%E7%A6%BB%E5%AD%90" title="碳正离子">碳陽離子</a>非常不穩定<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup>,所以會主要按照<a href="/wiki/%E5%8F%8C%E5%88%86%E5%AD%90%E4%BA%B2%E6%A0%B8%E5%8F%96%E4%BB%A3%E5%8F%8D%E5%BA%94" title="双分子亲核取代反应">雙分子</a>的<a href="/wiki/%E5%8F%8D%E5%BA%94%E6%9C%BA%E7%90%86" title="反应机理">機理</a>來進行<a href="/wiki/%E4%BA%B2%E6%A0%B8%E5%8F%96%E4%BB%A3%E5%8F%8D%E5%BA%94" title="亲核取代反应">親核取代反應</a>。<sup id="cite_ref-:2_12-0" class="reference"><a href="#cite_note-:2-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup>其中,<a href="/wiki/%E4%BA%B2%E6%A0%B8%E4%BD%93" title="亲核体">親核試劑</a>攻擊1-氯丙烷上連著氯原子的碳,氯以<a href="/wiki/%E6%B0%AF%E5%8C%96%E7%89%A9" title="氯化物">氯離子</a>的形式離去。1-氯丙烷的親核取代反應可以實現官能團轉換和碳鏈增長,用以合成新的有機化合物。 </p><p>例如,1-氯丙烷可以與<a href="/wiki/%E6%B0%A2%E6%B0%A7%E5%8C%96%E9%92%A0" title="氢氧化钠">氫氧化鈉</a><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup>發生<a href="/wiki/%E5%8F%8C%E5%88%86%E5%AD%90%E4%BA%B2%E6%A0%B8%E5%8F%96%E4%BB%A3%E5%8F%8D%E5%BA%94" title="双分子亲核取代反应">雙分子親核取代反應</a>,生成<a href="/wiki/%E6%AD%A3%E4%B8%99%E9%86%87" class="mw-redirect" title="正丙醇">正丙醇</a>。過程<a href="/wiki/%E6%B0%AF%E5%8C%96%E7%89%A9" title="氯化物">氯離子</a>被取代,為<a href="/wiki/%E9%9B%A2%E5%8E%BB%E5%9F%BA%E5%9C%98" title="離去基團">離去基團</a>,跟氫氧化鈉中的<a href="/wiki/%E9%88%89%E9%9B%A2%E5%AD%90" class="mw-redirect" title="鈉離子">鈉離子</a>結合生成<a href="/wiki/%E6%B0%AF%E5%8C%96%E9%92%A0" title="氯化钠">氯化鈉</a>。合成<a href="/wiki/%E8%83%BA" title="胺">胺</a>時,可以通過<a href="/wiki/%E5%8A%A0%E5%B8%83%E9%87%8C%E5%B0%94%E4%BC%AF%E8%83%BA%E5%90%88%E6%88%90%E5%8F%8D%E5%BA%94" title="加布里尔伯胺合成反应">加布里爾伯胺合成反應</a>來合成<a href="/wiki/%E4%B8%99%E8%83%BA" title="丙胺">丙胺</a>。<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup>它和<a href="/wiki/%E8%83%BA" title="胺">叔胺</a>反应,可以得到<a href="/wiki/%E5%AD%A3%E9%93%B5%E7%9B%90" title="季铵盐">季铵盐</a>。<sup id="cite_ref-OS_17-0" class="reference"><a href="#cite_note-OS-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="與金屬的反應"><span id=".E8.88.87.E9.87.91.E5.B1.AC.E7.9A.84.E5.8F.8D.E6.87.89"></span>與金屬的反應</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1-%E6%B0%AF%E4%B8%99%E7%83%B7&action=edit&section=5" title="编辑章节:與金屬的反應"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>可以與金屬<a href="/wiki/%E9%95%81" title="镁">鎂</a>反應在<a href="/wiki/%E5%9B%9B%E6%B0%A2%E5%91%8B%E5%96%83" title="四氢呋喃">四氫呋喃</a>或<a href="/wiki/%E4%B9%99%E9%86%9A" title="乙醚">乾乙醚</a>裏制得<a href="/wiki/%E6%A0%BC%E6%B0%8F%E8%AF%95%E5%89%82" title="格氏试剂">格氏試劑</a>,又或者與鋰金屬在乾乙醚在低溫中直接反應來製備<a href="/wiki/%E6%9C%89%E6%9C%BA%E9%94%82%E8%AF%95%E5%89%82" title="有机锂试剂">有機鋰試劑</a>。由於這些試劑很活潑,所以製造過程裏不能有二氧化碳和水。這些試劑都是很强的鹼,也是<a href="/wiki/%E4%BA%B2%E6%A0%B8%E4%BD%93" title="亲核体">親核試劑</a>,可以用來製備其他有機化合物。<sup id="cite_ref-:2_12-1" class="reference"><a href="#cite_note-:2-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="用途"><span id=".E7.94.A8.E9.80.94"></span>用途</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=1-%E6%B0%AF%E4%B8%99%E7%83%B7&action=edit&section=6" title="编辑章节:用途"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>多為工業生產的中間體<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup>,可以用來合成醫藥、農藥等有機化合物<sup id="cite_ref-:1_3-1" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>。亦可用作溶劑<sup id="cite_ref-:0_10-1" class="reference"><a href="#cite_note-:0-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup>。 </p> <div class="mw-heading mw-heading2"><h2 id="參考資料"><span id=".E5.8F.83.E8.80.83.E8.B3.87.E6.96.99"></span>參考資料</h2><span class="mw-editsection"><span 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John Wiley & Sons, Inc. 1983-07-27: 1–162 <span class="reference-accessdate"> [<span class="nowrap">2020-07-12</span>]</span>. <a href="/wiki/Special:%E7%BD%91%E7%BB%9C%E4%B9%A6%E6%BA%90/9780471264187" title="Special:网络书源/9780471264187"><span title="国际标准书号">ISBN</span> 9780471264187</a>. <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F0471264180.or029.01"><span title="數位物件識別號">doi:10.1002/0471264180.or029.01</span></a> <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%3A1-%E6%B0%AF%E4%B8%99%E7%83%B7&rft.au=Bertrand+R.+Castro&rft.btitle=Replacement+of+Alcoholic+Hydroxyl+Groups+by+Halogens+and+Other+Nucleophiles+via+Oxyphosphonium+Intermediates&rft.date=1983-07-27&rft.genre=book&rft.isbn=9780471264187&rft.pages=1-162&rft.pub=John+Wiley+%26+Sons%2C+Inc.&rft_id=http%3A%2F%2Fdoi.wiley.com%2F10.1002%2F0471264180.or029.01&rft_id=info%3Adoi%2F10.1002%2F0471264180.or029.01&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text">Leahy, Ellen M.; Zhang, Wenming. 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B. Hass, E. T. McBee, Paul Weber. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210804143345/https://pubs.acs.org/doi/abs/10.1021/ie50315a017">Chlorination of Paraffins 1</a>. Industrial & Engineering Chemistry. 1936-03, <b>28</b> (3): 333–339 <span class="reference-accessdate"> [<span class="nowrap">2020-07-12</span>]</span>. <a rel="nofollow" class="external text" href="//www.worldcat.org/issn/0019-7866"><span title="国际标准连续出版物号">ISSN 0019-7866</span></a>. <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fie50315a017"><span title="數位物件識別號">doi:10.1021/ie50315a017</span></a>. (<a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/abs/10.1021/ie50315a017">原始内容</a>存档于2021-08-04) <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%3A1-%E6%B0%AF%E4%B8%99%E7%83%B7&rft.atitle=Chlorination+of+Paraffins+1&rft.au=H.+B.+Hass%2C+E.+T.+McBee%2C+Paul+Weber&rft.date=1936-03&rft.genre=article&rft.issn=0019-7866&rft.issue=3&rft.jtitle=Industrial+%26+Engineering+Chemistry&rft.pages=333-339&rft.volume=28&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2Fabs%2F10.1021%2Fie50315a017&rft_id=info%3Adoi%2F10.1021%2Fie50315a017&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-:0-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_10-0"><sup><b>10.0</b></sup></a> <a href="#cite_ref-:0_10-1"><sup><b>10.1</b></sup></a></span> <span class="reference-text"><cite class="citation web"><a rel="nofollow" class="external text" href="http://www.basechem.org/chemical/3659">1-氯丙烷 1-Chloropropane</a>. 物競數據庫. <span class="reference-accessdate"> [<span class="nowrap">2022-07-16</span>]</span>. (原始内容<a rel="nofollow" class="external text" href="https://web.archive.org/web/20220716103358/http://www.basechem.org/chemical/3659">存档</a>于2022-07-16) <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>. <q>在三氯化铝存在下,200℃以下发生异构化,转变成2-氯丙烷。在氯化钡存在下,加热至380~400℃生成丙烯与2-氯丙烷。</q></cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A1-%E6%B0%AF%E4%B8%99%E7%83%B7&rft.atitle=1-%E6%B0%AF%E4%B8%99%E7%83%B7+1-Chloropropane&rft.genre=unknown&rft.jtitle=%E7%89%A9%E7%AB%B6%E6%95%B8%E6%93%9A%E5%BA%AB&rft_id=http%3A%2F%2Fwww.basechem.org%2Fchemical%2F3659&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><cite class="citation book">Anslyn, Eric V.; Dougherty, Dennis A. Modern Physical Organic Chemistry. Sausalito, CA: University Science Books. 2000. <a href="/wiki/Special:%E7%BD%91%E7%BB%9C%E4%B9%A6%E6%BA%90/978-1891389313" title="Special:网络书源/978-1891389313"><span title="国际标准书号">ISBN</span> 978-1891389313</a>.</cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A1-%E6%B0%AF%E4%B8%99%E7%83%B7&rft.au=Dougherty%2C+Dennis+A.&rft.aufirst=Eric+V.&rft.aulast=Anslyn&rft.btitle=Modern+Physical+Organic+Chemistry&rft.date=2000&rft.genre=book&rft.isbn=978-1891389313&rft.place=Sausalito%2C+CA&rft.pub=University+Science+Books&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-:2-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-:2_12-0"><sup><b>12.0</b></sup></a> <a href="#cite_ref-:2_12-1"><sup><b>12.1</b></sup></a></span> <span class="reference-text"><cite class="citation book">邢, 其毅; 裴, 偉偉; 徐, 瑞秋; 裴, 堅. 第6章. <a rel="nofollow" class="external text" href="https://archive.org/details/isbn_9787301272121_1">基礎有機化學</a>. 北京. 2016: <a rel="nofollow" class="external text" href="https://archive.org/details/isbn_9787301272121_1/page/239">239</a>-241. <a href="/wiki/Special:%E7%BD%91%E7%BB%9C%E4%B9%A6%E6%BA%90/978-7-301-27212-1" title="Special:网络书源/978-7-301-27212-1"><span title="国际标准书号">ISBN</span> 978-7-301-27212-1</a>.</cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A1-%E6%B0%AF%E4%B8%99%E7%83%B7&rft.atitle=%E7%AC%AC6%E7%AB%A0&rft.au=%E5%BE%90%2C+%E7%91%9E%E7%A7%8B&rft.au=%E8%A3%B4%2C+%E5%81%89%E5%81%89&rft.au=%E8%A3%B4%2C+%E5%A0%85&rft.aufirst=%E5%85%B6%E6%AF%85&rft.aulast=%E9%82%A2&rft.btitle=%E5%9F%BA%E7%A4%8E%E6%9C%89%E6%A9%9F%E5%8C%96%E5%AD%B8&rft.date=2016&rft.genre=bookitem&rft.isbn=978-7-301-27212-1&rft.pages=239-241&rft.place=%E5%8C%97%E4%BA%AC&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fisbn_9787301272121_1&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text">Smith, W. Novis; McCloskey, Joel. Preparation of tetrafluoroborate salts and their tetraalkyl ammonium halide intermediates. 2002. US 6444846 B1.</span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><cite class="citation journal">Gabriel, S. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200410041334/https://gallica.bnf.fr/ark:/12148/bpt6k90711d/f133.chemindefer">Ueber eine Darstellung primärer Amine aus den entsprechenden Halogenverbindungen</a>. <a href="/wiki/Chemische_Berichte" class="mw-redirect" title="Chemische Berichte">Ber.</a> 1887, <b>20</b>: 2224 <span class="reference-accessdate"> [<span class="nowrap">2009-01-31</span>]</span>. (<a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k90711d/f133.chemindefer">原始内容</a>存档于2020-04-10).</cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A1-%E6%B0%AF%E4%B8%99%E7%83%B7&rft.atitle=Ueber+eine+Darstellung+prim%C3%A4rer+Amine+aus+den+entsprechenden+Halogenverbindungen&rft.au=Gabriel%2C+S.&rft.date=1887&rft.genre=article&rft.jtitle=Ber.&rft.pages=2224&rft.volume=20&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k90711d%2Ff133.chemindefer&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><cite class="citation journal">Sheehan, J. C.; Bolhofer, V. A. An Improved Procedure for the Condensation of Potassium Phthalimide with Organic Halides. <a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a> 1950, <b>72</b>: 2786. <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01162a527"><span title="數位物件識別號">doi:10.1021/ja01162a527</span></a>.</cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A1-%E6%B0%AF%E4%B8%99%E7%83%B7&rft.atitle=An+Improved+Procedure+for+the+Condensation+of+Potassium+Phthalimide+with+Organic+Halides&rft.au=Sheehan%2C+J.+C.%3B+Bolhofer%2C+V.+A.&rft.date=1950&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.pages=2786&rft.volume=72&rft_id=info%3Adoi%2F10.1021%2Fja01162a527&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><cite class="citation journal">Gibson, M.S.; Bradshaw, R.W. The Gabriel Synthesis of Primary Amines. <a href="/wiki/Angew._Chem._Int._Ed._Engl." class="mw-redirect" title="Angew. Chem. Int. Ed. Engl.">Angew. Chem. Int. Ed. Engl.</a> 1968, <b>7</b>: 919. <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.196809191"><span title="數位物件識別號">doi:10.1002/anie.196809191</span></a>.</cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A1-%E6%B0%AF%E4%B8%99%E7%83%B7&rft.atitle=The+Gabriel+Synthesis+of+Primary+Amines&rft.au=Gibson%2C+M.S.%3B+Bradshaw%2C+R.W.&rft.date=1968&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.+Engl.&rft.pages=919&rft.volume=7&rft_id=info%3Adoi%2F10.1002%2Fanie.196809191&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-OS-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-OS_17-0">^</a></b></span> <span class="reference-text"><cite class="citation journal">Brasen, W. R.; Hauser, C. R. o-Methylbenzyl Alcohol. Organic Syntheses. 1954, <b>34</b>: 58. <a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.034.0058"><span title="數位物件識別號">doi:10.15227/orgsyn.034.0058</span></a>.</cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A1-%E6%B0%AF%E4%B8%99%E7%83%B7&rft.atitle=o-Methylbenzyl+Alcohol&rft.au=Hauser%2C+C.+R.&rft.aufirst=W.+R.&rft.aulast=Brasen&rft.date=1954&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.pages=58&rft.volume=34&rft_id=info%3Adoi%2F10.15227%2Forgsyn.034.0058&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;"> </span></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><cite class="citation web"><a rel="nofollow" class="external text" href="https://www.epa.gov/chemical-data-reporting">chemical-data-reporting</a>. 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