Everything about Bromoethane totally explained
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| FlashPt = −20 °C
| Autoignition = 511 °C
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Bromoethane, also known as
ethyl bromide is a
chemical compound of the
haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odour.
Synthesis
The preparation of EtBr stands as a model for the synthesis of alkyl bromides in general. It is usually prepared by the addition of
HBr to ethylene:
» H
2C=CH
2 + HBr → H
3C-CH
2Br
Ethyl bromide is inexpensive and would rarely be prepared in the laboratory. Convenient laboratory syntheses include the action of phosphorus tribromide or thionyl bromide on ethanol. EtBr forms when
ethanol is treated with
HBr or
hydrobromic acid, although this reaction also affords
diethyl ether.
Uses
In
organic synthesis, EtBr is the synthetic equivalent of the ethyl
carbocation (Et
+)
synthon. In reality, such a cation isn't actually formed. For example, carboxylates salts are converted to ethyl
esters,
carbanions to ethylated derivatives, thiourea into ethylisothiouronium salts, and
amines into ethylamines.
Being a liquid at room temperature but still very volatile, EtBr is an inexpensive reagent for the preparation of
Grignard reagents, which traditionally were used as strong base. Thus EtMgBr deprotonates
alkynes:
» EtBr + Mg → EtMgBr
RC≡CH + EtMgBr → RC≡CMgBr +
EtH
This application has been supplanted by the wide availability of organolithium reagents.
Safety
Halocarbons in general are potentially dangerous alkylating agents. Bromides are more superior alkylating agents than chlorides, thus exposure to EtBr should be minimized. EtBr is classified by the State of California as carcinogenic and a reproductive toxin.
Further Information
Get more info on 'Bromoethane'.
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