Bromoethane

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Bromoethane
Skeletal formula of bromoethane
Skeletal formula of bromoethane with all explicit hydrogens added
Ball and stick model of bromoethane
Spacefill model of bromoethane
Names
IUPAC name
Bromoethane[2]
Other names
Ethyl bromide[1]
Monobromoethane[1]
Identifiers
74-96-4 YesY
1209224
ChEMBL ChEMBL156378 YesY
ChemSpider 6092 YesY
EC Number 200-825-8
Jmol 3D model Interactive image
KEGG C19354 N
MeSH bromoethane
PubChem 6332
RTECS number KH6475000
UN number 1891
  • InChI=1S/C2H5Br/c1-2-3/h2H2,1H3 YesY
    Key: RDHPKYGYEGBMSE-UHFFFAOYSA-N YesY
  • CCBr
Properties
C2H5Br
Molar mass 108.97 g·mol−1
Appearance Colorless liquid
Odor ether-like
Density 1.46 g mL−1
Melting point −120 to −116 °C; −184 to −177 °F; 153 to 157 K
Boiling point 38.0 to 38.8 °C; 100.3 to 101.8 °F; 311.1 to 311.9 K
1.067 g/100 mL (0 °C)
0.914 g/100 mL (20 °C)
0.896 g/100 mL (30 °C)
Solubility miscible with ethanol, ether, chloroform, organic solvents
log P 1.809
Vapor pressure 51.97 kPa (at 20 °C)
1.3 μmol Pa−1 kg−1
1.4225
Viscosity 402 Pa s (at 20 °C)
Thermochemistry
105.8 J K−1 mol−1
−97.6–93.4 kJ mol−1
Vapor pressure {{{value}}}
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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.

Preparation

The preparation of EtBr stands as a model for the synthesis of bromoalkanes in general. It is usually prepared by the addition of HBr 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.[3]

Uses

In organic synthesis, EtBr is the synthetic equivalent of the ethyl carbocation (Et+) synthon.[4] In reality, such a cation is not actually formed. For example, carboxylates salts are converted to ethyl esters,[5] carbanions to ethylated derivatives, thiourea into ethylisothiouronium salts,[6] and amines into ethylamines.[7]

Safety

Halocarbons in general are potentially dangerous alkylating agents. Bromides are better 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.

References

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External links

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