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Bromoethane

Monobromoethane 0.914 g/100 mL (20 °C) 0.896 g/100 mL (30 °C) |NFPA-H = 3 |NFPA-F = 1 |NFPA-R = 0 16,230 ppm (mouse, 1 hr) 4681 ppm (rat) 2723 ppm (mouse) 24,000 ppm (guinea pig, 30 min) 7000 ppm (guinea pig, 4.5 hr) 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.

References

References

  1. (26 March 2005). "bromoethane - Compound Summary". National Center for Biotechnology Information.
  2. {{PGCH. 0265
  3. {{IDLH. 74964. Ethyl bromide
  4. Oliver Kamm. (1941). "Alkyl and alkylene bromides".
  5. Makosza, M.. "Phase-Transfer Alkylation of Nitriles: 2-Phenylbutyronitrile".
  6. Petit, Y.. "Ethyl Glycidate from (S)-Serine: Ethyl (R)-(+)-2,3-Epoxypropanoate".
  7. E. Brand. "Guanidodacetic Acid".
  8. Brasen, W. R. "o-Methylethylbenzyl Alcohol".
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bromoalkanes ethylating-agents iarc-group-3-carcinogens ozone-depleting-chemical-substances
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