查看“︁氯乙醛”︁的源代码

{{chembox
| Watchedfields = changed
| verifiedrevid = 443517733
| ImageFile =Chloroacetaldehyde_Structural_Formula_V1.svg
| ImageName = 结构式
| ImageFile1 = Chloroacetaldehyde-3D-balls.png
| ImageName1 = 球棍模型
| IUPACName = Chloroacetaldehyde
| OtherNames = 一氯代乙醛，一氯乙醛，2-氯乙醛
| SystematicName = Chloroethanal
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = CF069F5D9C
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 61S63ROQ1E
| UNII1_Comment =水合物
| ChemSpiderID = 32
| PubChem = 33
| CASNo = 107-20-0
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 34789-09-8
| CASNo2_Comment =水合物
| CASNo_Ref = {{cascite|correct|CAS}}
| RTECS = 
| InChI = 1S/C2H3ClO/c3-1-2-4/h2H,1H2
| InChIKey = QSKPIOLLBIHNAC-UHFFFAOYSA-N
| SMILES = C(C=O)Cl
| EINECS = 203-472-8
  }}
| Section2 = {{Chembox Properties
|  Formula = C<sub>2</sub>H<sub>3</sub>ClO
|  MolarMass = 78.50
|  Appearance = 无色液体<ref name="GESTIS">{{GESTIS|ZVG=19990|CAS=107-20-0|Name=Chloracetaldehyd|Abruf=2016-02-01}}</ref>
| Odor =辛辣，有穿透性<ref name=":me"/>
|  Density = 1.19 g/cm<sup>3</sup><ref name="GESTIS" />
|  Solubility = 443 g/L<ref name="GESTIS" /><ref name="Römpp" />
|SolubleOther=可溶于有机溶剂<ref name="Römpp" />
|  MeltingPtC = -16.3
|  BoilingPtCL = 85
|BoilingPtCH=86
|Melting_notes=<ref name="GESTIS" />
|Boiling_notes=<ref name="GESTIS" /><ref name="Römpp">{{RömppOnline|ID=RD-03-01357|Name=Chloracetaldehyd|Datum=2015-04-17}}</ref><ref name="eEROS"/>
|  pKa =
|  RefractIndex = (<math>\ n_D^{25}</math>) 1.397<ref name="zghg" />
  }}
| Section7 = {{Chembox Hazards
|  ExternalMSDS =
|  EUIndex =
|  EUClass = {{Chembox EUHazardSymbol|T+|N}}<ref name="cb">{{ChemicalBook|6676908|氯乙醛}}</ref>
|  MainHazards = 烷化剂
|  NFPA-H =
|  NFPA-F =
|  NFPA-R =
|  FlashPt = 87.78 °C<ref name="zghg">中国化工产品大全 上卷，Da137 （一）氯乙醛，页511</ref>
|  RPhrases = {{R24/25}}-{{R26}}-{{R34}}-{{R40}}-{{R50}}<ref name="cb" />
|  SPhrases = {{S26}}-{{S28}}-{{S36/37/39}}-{{S45}}-{{S61}}<ref name="cb" />
| LD50 = 89 mg/kg（大鼠，口服）<br/>82 mg/kg（小鼠，口服）<ref>{{cite web |url = https://www.cdc.gov/niosh/idlh/107200.html |title = Chloroacetaldehyde |publisher = National Institute for Occupational Safety and Health |date = 2014-12-04 |accessdate = 2015-02-20 |archive-date = 2023-03-30 |archive-url = https://web.archive.org/web/20230330083507/https://www.cdc.gov/niosh/idlh/107200.html |dead-url = no }}</ref>
| LC50 = 200 ppm（大鼠，1小时）<ref>{{IDLH|107200|Chloroacetaldehyde}}</ref>
| PEL = C 1 ppm（3 mg/m<sup>3</sup>）<ref name=PGCH>{{PGCH|0118}}</ref>
| REL = C 1 ppm（3 mg/m<sup>3</sup>）<ref name=PGCH/>
| IDLH = 45 ppm<ref name=PGCH/>
  }}
| Section8 = {{Chembox Related
|  OtherCpds = [[氯乙醇]]<br />[[氯乙酸]]<br />[[二氯乙醛]]<br />[[三氯乙醛]]
  }}
}}
'''氯乙醛'''是一种[[有机化合物]]，结构式[[C2H3ClO|ClCH<sub>2</sub>CHO]]。它是无色具刺鼻辛辣气味的液体，也是强[[亲电试剂]]和危险的[[烷基化试剂]]。氯乙醛通常不以[[无水物]]存在，而是以半缩水合醛(ClCH<sub>2</sub>CH(OH))<sub>2</sub>O形式存在。它可用于有机合成。

氯乙醛是抗肿瘤药[[异环磷酰胺]]的代谢产物，被认为是异环磷酰胺某些毒性的来源。<ref>{{cite journal | last=Springate | first=James E. | title=Ifosfamide Metabolite Chloroacetaldehyde Causes Renal Dysfunctionin vivo | journal=Journal of Applied Toxicology | publisher=Wiley | volume=17 | issue=1 | year=1997 | issn=0260-437X | doi=10.1002/(sici)1099-1263(199701)17:1<75::aid-jat397>3.0.co;2-c | pages=75–79}}</ref>氯乙醛也是[[氯乙烯]]和[[1,2-二氯乙烷]]的代谢产物。<ref>{{cite book | last=Proctor | first=Nick H. | last2=Hughes | first2=James P. | last3=Hathaway | first3=Gloria J. | title=Proctor and Hughes' Chemical hazards of the workplace. | publisher=Wiley-Interscience | publication-place=Hoboken, N.J. | date=2004 | isbn=0-471-26883-6 | oclc=53369421}}</ref>它会腐蚀[[粘膜]]及刺激眼睛、皮肤和呼吸道。<ref name=":me">{{Cite book|title=The Merck index|url=https://archive.org/details/merckindexencycl0000unse|date=1996|publisher=Merck|others=S Budavari, M O'Neil, A Smith|isbn=9780911910124|edition=12|pages=[https://archive.org/details/merckindexencycl0000unse/page/n370 2108]}}</ref>

== 制备 ==
把[[乙醛]]或[[三聚乙醛]]氯化能得到氯乙醛<ref name=":me" />。反应也会产生[[二氯乙醛]]和[[三氯乙醛]]<ref name="Ullmann"/>，而这三者都是[[乙烯]]通过[[瓦克尔法]]转化成[[乙醛]]时产生的副产物。<ref name="Ullmann">{{cite | last=Jira | first=Reinhard | last2=Kopp | first2=Erwin | last3=McKusick | first3=Blaine C. | last4=Röderer | first4=Gerhard | last5=Bosch | first5=Axel | last6=Fleischmann | first6=Gerald | title=Chloroacetaldehydes | publisher=Wiley | date=2007-07-15 | isbn=978-3-527-30385-4 | doi=10.1002/14356007.a06_527.pub2}}</ref>无水氯乙醛可由[[高碘酸盐]]氧化[[3-氯-1,2-丙二醇]]而成。<ref name="eEROS"/><ref>{{cite journal | last=Hatch | first=Lewis F. | last2=Alexander | first2=Harold E. | title=Preparation of Chloroacetaldehyde Hydrate | journal=Journal of the American Chemical Society | publisher=American Chemical Society (ACS) | volume=67 | issue=4 | year=1945 | issn=0002-7863 | doi=10.1021/ja01220a504 | pages=688–688}}</ref>氯乙醛还能通过[[氯乙烯]]和[[氯水]]的反应产生：<ref name="Ullmann"/>
:ClCH=CH<sub>2</sub> + Cl<sub>2</sub> + H<sub>2</sub>O → ClCH<sub>2</sub>CHO + 2 HCl

除此之外，氯乙醛还可以通过[[一氯代碳酸乙烯酯]]的分解产生。<ref name="Ullmann"/><ref>{{cite journal | last=Gross | first=Hans | title=Über ?-Halogenäther. XVI. Monochloracetaldehyd bzw. Derivate des Glykolaldehyds und Glyoxals aus ?-Halogenäthern | journal=Journal für Praktische Chemie | publisher=Wiley | volume=21 | issue=1-2 | year=1963 | issn=0021-8383 | doi=10.1002/prac.19630210115 | pages=99–102 | language=de}}</ref>
:[[File:Chloroacetaldehyde synthesis01.svg|395px]]

==反应==
无水氯乙醛在室温下容易聚合成三聚体、四聚体或多聚体。<ref name="Ullmann"/>氯乙醛也会和水反应，生成缩醛半水合物1,1'-二羟基-2,2'-二氯乙醚。<ref name="Ullmann"/>这种化合物是无色晶体，熔点43－50 °C，沸点84 °C，并分解成氯乙醛和水。<ref name="Ullmann"/>
:[[File:Chloroacetaldehyde reaction01.svg|450px]]

这种半水合物可被浓[[硫酸]]脱水，生成三聚氯乙醛（2,4,6-三(氯甲基)-1,3,5-三𫫇烷）。<ref name="Ullmann"/><ref>{{cite journal | last=Natterer | first=Konrad | title=Über Monochloraldehyd | journal=Monatshefte für Chemie | publisher=Springer Science and Business Media LLC | volume=3 | issue=1 | year=1882 | issn=0026-9247 | doi=10.1007/bf01516819 | pages=442–464 | language=de}}</ref>它是无色晶体，熔点88–89 °C。<ref name="Ullmann"/>
:[[File:Chloroacetaldehyde reaction02.svg|500px]]

半水合物通过[[共沸蒸馏]]脱水得到的是四聚氯乙醛（2,4,6,8-四(氯甲基)-1,3,5,7-四氧杂环辛烷）。<ref name="Kopp">{{cite journal | last=Kopp | first=Erwin | last2=Smidt | first2=Jürgen | title=Reaktionen mit Chloracetaldehyd und 2.4-Dichlor-crotonaldehyd | journal=Justus Liebigs Annalen der Chemie | publisher=Wiley | volume=693 | issue=1 | date=1966-05-31 | issn=0075-4617 | doi=10.1002/jlac.19666930110 | pages=117–127 | language=de}}</ref><ref name="Ullmann"/>和三聚体一样，它也是无色晶体，熔点65–67 °C。<ref name="Ullmann"/>
:[[File:Chloroacetaldehyde reaction03.svg|500px]]

用[[硝酸]]或[[过氧化氢]]等氧化剂氧化氯乙醛可以得到[[氯乙酸]]。<ref name="Ullmann"/>

== 用途 ==
氯乙醛是有机合成原料<ref name="eEROS">e-EROS Encyclopedia of Reagents for Organic Synthesis, 1999–2013, John Wiley and Sons, Inc., Eintrag für Chloroacetaldehyde, abgerufen am ''4. November 2015''.</ref>，可以合成[[吡咯]]<ref>{{cite journal | last=Quijano | first=M. Luisa | last2=Nogueras | first2=Manuel | last3=Sánchez | first3=Aldolfo | last4=De Cienfuegos | first4=Gerardo Alvarez | last5=Melgarejo | first5=Miguel | title=Synthesis, anticancer and antimicrobiological activities of pyrrolo[2,3-d]pyrimidines | journal=Journal of Heterocyclic Chemistry | publisher=Wiley | volume=27 | issue=4 | year=1990 | issn=0022-152X | doi=10.1002/jhet.5570270449 | pages=1079–1083}}</ref>、[[呋喃]]<ref>{{cite journal | last=Padwa | first=Albert | last2=Gasdaska | first2=John R. | title=Generation of sulfur ylides by the desilylation of α-trimethylsilylbenzyl sulfonium salts | url=https://archive.org/details/sim_tetrahedron_1988_44_13/page/4147 | journal=Tetrahedron | publisher=Elsevier BV | volume=44 | issue=13 | year=1988 | issn=0040-4020 | doi=10.1016/s0040-4020(01)86662-x | pages=4147–4156}}</ref><ref>{{cite journal | last=Matsumoto | first=Masakatsu | last2=Watanabe | first2=Nobuko | title=A Facile Synthesis of 4-Oxo-4,5,6,7-tetrahydroindoles | journal=HETEROCYCLES | publisher=The Japan Institute of Heterocyclic Chemistry | volume=22 | issue=10 | year=1984 | issn=0385-5414 | doi=10.3987/r-1984-10-2313 | page=2313}}</ref>、[[噻吩]]<ref>{{cite journal | last=Hirota | first=Kosaku | last2=Shirahashi | first2=Mitsuomi | last3=Senda | first3=Shigeo | last4=Yogo | first4=Motoi | title=Pyrimidines. 65. Synthesis of 6-substituted thieno[2,3-d]pyrimidine-2,4(1H,3H)-diones | journal=Journal of Heterocyclic Chemistry | publisher=Wiley | volume=27 | issue=3 | year=1990 | issn=0022-152X | doi=10.1002/jhet.5570270345 | pages=717–721}}</ref><ref>{{cite journal | last=Aldvogel | first=Erwin | title=Synthese von 2-substituierten und 2,3-disubstituierten Alkyl- und Aryl-thiophenen und 2,3-anellierten Thiophen-Derivaten aus Ketonen als C2-Bausteine und Carbonodithiosäure-O-ethyl-S-(2-oxoethyl)ester als C2S-Baustein | journal=Helvetica Chimica Acta | publisher=Wiley | volume=75 | issue=3 | date=1992-05-06 | issn=0018-019X | doi=10.1002/hlca.19920750325 | pages=907–912}}</ref>、[[咪唑]]<ref>{{cite journal | last=Kluge | first=Arthur F. | title=Synthesis of an imidazo[1,2-c]pyrimidine analog of a thiamine antagonist coccidiostat and a comparison of several methods for the preparation of imidazo[1,2-c]pyrimidines | journal=Journal of Heterocyclic Chemistry | publisher=Wiley | volume=15 | issue=1 | year=1978 | issn=0022-152X | doi=10.1002/jhet.5570150125 | pages=119–121}}</ref><ref>{{cite journal | last=Senga | first=Keitaro | last2=Robins | first2=Roland K. | last3=O'Brien | first3=Darrell E. | title=Synthesis of certain imidazo[2,1-f] pyrazolo[3,4-d] pyrimidines | journal=Journal of Heterocyclic Chemistry | publisher=Wiley | volume=12 | issue=5 | year=1975 | issn=0022-152X | doi=10.1002/jhet.5570120547 | pages=1043–1044}}</ref>、[[𫫇唑啉]]<ref>{{cite journal | last=Weber | first=Maya | last2=Jakobxht | first2=Jürgen | last3=Martens | first3=Jürgen | title=Synthese und Reaktivität von 3-Oxazolinen | journal=Liebigs Annalen der Chemie | publisher=Wiley | volume=1992 | issue=1 | date=1992-01-13 | issn=0170-2041 | doi=10.1002/jlac.199219920102 | pages=1–6 | language=de}}</ref>、{{le|噻唑啉|Thiazoline}}<ref>{{cite journal | last=Martens | first=Jürgen | last2=Offermanns | first2=Heribert | last3=Scherberich | first3=Paul | title=Einfache Synthese von racemischem Cystein | journal=Angewandte Chemie | publisher=Wiley | volume=93 | issue=8 | year=1981 | issn=0044-8249 | doi=10.1002/ange.19810930808 | pages=680–683 | language=de}}</ref>、[[噻唑]]<ref>{{cite journal | last=Begtrup | first=Mikael | last2=Hansen | first2=Lars Bo L. | last3=Grundvig | first3=S. | last4=Stenstrøm | first4=Yngve | last5=Khan | first5=Agha Zul-Quarnain | last6=Sandström | first6=Jan | last7=Krogsgaard-Larsen | first7=Povl | title=New Methods for the Introduction of Substituents into Thiazoles. | journal=Acta Chemica Scandinavica | publisher=Danish Chemical Society | volume=46 | year=1992 | issn=0904-213X | doi=10.3891/acta.chem.scand.46-0372 | pages=372–383}}</ref><ref>{{cite journal | last=Brandsma | first=L. | last2=De Jong | first2=R. L. P. | last3=Verkruijsse | first3=H. D. | title=An Efficient Synthesis of 1,3-Thiazole | url=https://archive.org/details/sim_synthesis_1985-10_10/page/948 | journal=Synthesis | publisher=Georg Thieme Verlag KG | volume=1985 | issue=10 | year=1985 | issn=0039-7881 | doi=10.1055/s-1985-31396 | pages=948–949}}</ref>和[[吲哚]]<ref>{{cite journal | last=Wender | first=Paul A. | last2=White | first2=Alan W. | title=Methodology for the facile and regio-controlled synthesis of indoles | journal=Tetrahedron | publisher=Elsevier BV | volume=39 | issue=22 | year=1983 | issn=0040-4020 | doi=10.1016/s0040-4020(01)88618-x | pages=3767–3776}}</ref>。此外，氯乙醛也是生产[[药品]]、[[杀虫剂]]、[[杀真菌剂]]、[[消毒剂]]、[[染料]]、[[环氧树脂]]硬化剂和[[抗静电剂]]的原料。<ref name="Römpp" />它也用于去除[[树皮]]。<ref name=":me" />

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== 参考资料 ==
{{reflist|30em}}

[[Category:二碳有机物]]
[[Category:醛]]
[[Category:有机氯化合物]]
[[Category:缺少物质图片的化学品条目]]