Bromoethane

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Bromoethane

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Template:Longitem	1209224
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MeSH	bromoethane
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UN number	1891
Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Colorless liquid
Odor	ether-like
Density	1.46 g mL−1
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Solubility	miscible with ethanol, ether, chloroform, organic solvents
log P	1.809
Vapor pressure	51.97 kPa (at 20 °C)
Template:Longitem	1.3 μmol Pa−1 kg−1
Template:Longitem	−54.70·10−6 cm3/mol
Template:Longitem	1.4225
Viscosity	402 Pa.s (at 20 °C)
Template:Longitem	105.8 J K−1 mol−1
Template:Longitem	−97.6–93.4 kJ mol−1
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Explosive limits	6.75–11.25%
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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 (which is also used as an abbreviation for ethidium bromide). This volatile compound has an ether-like odor.

Preparation

The preparation of EtBr stands as a model for the synthesis of bromoalkanes in general. It is usually prepared by the addition of hydrogen bromide to ethene:

H₂C=CH₂ + HBr → H₃C-CH₂Br

Bromoethane is inexpensive and would rarely be prepared in the laboratory. A laboratory synthesis includes reacting ethanol with a mixture of hydrobromic and sulfuric acids. An alternate route involves refluxing ethanol with phosphorus and bromine; phosphorus tribromide is generated in situ.

Uses

In organic synthesis, EtBr is the synthetic equivalent of the ethyl carbocation (Et⁺) synthon. In reality, such a cation is not actually formed. For example, carboxylates salts are converted to ethyl esters, carbanions to ethylated derivatives, thiourea into ethylisothiouronium salts, and amines into ethylamines.

Safety

Short chain monohalocarbons in general are potentially dangerous alkylating agents. Bromides are better alkylating agents than chlorides, thus exposure to them should be minimized.

External links

• International Chemical Safety Card 1378
• NIOSH Pocket Guide to Chemical Hazards
• IARC Monograph: "Bromoethane"