查看“︁溴乙烷”︁的源代码

{{Chembox
| Name = 溴乙烷
| ImageFileL1 = Bromoethane.png
| ImageSizeL1 = 120px
| ImageNameL1 = 骨架式
| ImageFileR1 = Bromoethane-3D-vdW.png
| ImageSizeR1 = 120px
| ImageNameR1 = 3D模型
| IUPACName = Bromoethane
| IUPACNameZh = 溴乙烷
| SystematicName = 
| OtherNames = 乙基溴（Ethyl bromide）
| Section1 = {{Chembox Identifiers
| CASNo = 74-96-4
| CASNo_Ref = {{cascite|correct|CAS}}
|  EINECS  =  
|  PubChem  =  
|  SMILES  =  CCBr
|  InChI  = |  RTECS  =  KH6475000
|  ChemSpiderID  =  6092
|  ChemSpiderID_Ref  = {{chemspidercite|correct|chemspider}}|  UNNumber  =  1891
|  KEGG  =  C19354
|  KEGG_Ref  = {{keggcite|changed|kegg}}|  MeSHName  =  bromoethane
|  ChEMBL  =  156378
|  ChEMBL_Ref  = {{ebicite|correct|EBI}}|  Beilstein  =  1209224
|  StdInChI  =  1S/C2H5Br/c1-2-3/h2H2,1H3
|  StdInChI_Ref  = {{stdinchicite|correct|chemspider}}|  StdInChIKey  =  RDHPKYGYEGBMSE-UHFFFAOYSA-N
|  StdInChIKey_Ref  = {{stdinchicite|correct|chemspider}}
}}
| Section2 = {{Chembox Properties
|   Formula = C<sub>2</sub>H<sub>5</sub>Br
|   MolarMass = 108.97 
|   Appearance = 無色液體
|   Density = 1.47 g/cm<sup>3</sup> (液)
|   Solubility = 0.91 g/100 ml (20&nbsp;°C)
|   MeltingPt = −119&nbsp;°C (154 K)
|   BoilingPt = 38.4&nbsp;°C
|   Viscosity = 0.402 [[泊 (单位)|cP]], 20&nbsp;°C
  }}
| Section3 = {{Chembox Structure
|   Dipole =
  }}
| Section7 = {{Chembox Hazards
|   ExternalMSDS =
|   EUClass = 可燃 ('''F''')<br />[[致癌物质|Carc. Cat. 3]]<br />有害 ('''Xn''')
|   NFPA-H = 2
|   NFPA-F = 1
|   NFPA-R =
|   RPhrases = {{R11}}, {{R20/22}}, {{R40}}
|   SPhrases = {{S2}}, {{S36/37}}
|   FlashPt = −20&nbsp;°C
|   Autoignition = 511&nbsp;°C
|   ExploLimits = 6.8–11%
  }}
| Section8 = {{Chembox Related
|   Function = [[卤代烃]]
|   OtherFunctn = [[溴甲烷]]、[[氯乙烷]]、<br />[[碘乙烷]]
  }}
}}
'''溴乙烷'''（化學式：[[碳|C]]<sub>2</sub>[[氢|H]]<sub>5</sub>[[溴|Br]]）又名'''乙基溴'''，是一种[[鹵代烃]]，縮寫为'''EtBr'''。這種易揮發的化合物帶有跟[[醚]]相似的氣味。

== 合成 ==
与其他溴代烷类似，EtBr可由在乙烯中加入[[溴化氫]]來製備：

:H<sub>2</sub>C=CH<sub>2</sub>  +  [[溴化氫|HBr]]  →  H<sub>3</sub>C-CH<sub>2</sub>Br

乙基溴并不昂貴，因此很少會於實驗室中製備。合宜的實驗室合成包括[[三溴化磷]]或[[亞硫醯溴]]作用於[[乙醇]]。當用[[溴化氫]]或[[氫溴酸]]來處理[[乙醇]]时，会生成EtBr，副产物是[[乙醚]]。

== 化学性质 ==
溴乙烷可以在热的[[氢氧化钠]]水溶液中发生[[水解]]：
EtBr + NaOH <math>\to</math> [[乙醇|EtOH]] + [[溴化钠|NaBr]]

溴乙烷还可以在热的[[氢氧化钠]]醇溶液中发生[[消去]]：
EtBr + NaOH <math>\to</math> [[乙烯|CH<sub>2</sub>=CH<sub>2</sub>]] + [[溴化钠|NaBr]] + H<sub>2</sub>O

== 用途 ==
在[[有機合成]]中，EtBr是假想乙基[[碳正離子]]（[[乙基|Et]]<sup>+</sup>）的[[合成子]]。例如可将由[[羧酸鹽]]轉化為乙酯，<ref> Petit, Y.; Larchevêque, M. ''Ethyl Glycidate from (S)-Serine: Ethyl (R)-(+)-2,3-Epoxypropanoate'' </ref>[[碳負離子]]至[[乙基]]衍生物，[[硫脲]]至乙基異硫脲鹽， <ref> E. Brand, E.; Brand, F. C. ''Guanidodacetic Acid'' </ref>及[[胺]]至乙基胺。<ref> Brasen, W. R; Hauser, C. R. ''o-Methylethylbenzyl Alcohol''</ref>

即使此液體存在於室溫，仍然很易揮發。EtBr常用作製備强碱性的[[格林尼亞試劑]]，如EtMgBr可使[[炔]]失去質子：<ref> Taniguchi, H.; Mathai, I. M.; Miller, S. I. ''1-Phenyl-1,4-Pentadiyne and 1-Phenyl-1,3-Pentadiyne'' </ref> <ref> A. J. Quillinan, A. J.; Scheinmann, F. ''3-Alkyl-1-alkynes Synthesis: 3-Ethyle-1-hexyne'' </ref> <!--double deprotonation of hexyne followed by ethylation--> <ref>Newman, M. S.; Stalick, W. M. ''1-Ethoxy-1-butyne''</ref> <!--ethylation of acetylide-->

:EtBr  + Mg  →  EtMgBr

:RC≡CH  +  EtMgBr  →  RC≡CMgBr  +  [[乙烷|EtH]]

此應用已被有機鋰試劑廣泛取代。

== 安全 ==
[[卤代烃]]通常是帶有潛在危險的烷基化劑，[[溴化物]]較[[氯化物]]烷基化能力更强，因此应尽量避免接触EtBr。EtBr被[[美國]][[加州]]列入[[致癌]]物質及一種生殖上的[[毒素]]。

== 參考資料及注釋 ==
<references/>
* Makosza, M.; Jonczyk, A. ''Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile'' <!--alpha-ethylation of benzylcyanide-->

== 外部連結 ==
* [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc13/icsc1378.htm 國際化學安全名片 1378] {{Wayback|url=http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc13/icsc1378.htm |date=20080504105218 }}
* [http://www.cdc.gov/niosh/npg/npgd0265.html 局部化學危險指南---NIOSH] {{Wayback|url=http://www.cdc.gov/niosh/npg/npgd0265.html |date=20210323203728 }}
* [https://web.archive.org/web/20051012221857/http://www-cie.iarc.fr/htdocs/monographs/vol71/068-bromoeth.html IARC 專題論文：溴乙烷]


{{卤代乙烷}}
{{Authority control}}
[[Category:溴代烷烃]]
[[Category:乙基化试剂]]
[[Category:IARC第3类致癌物质]]