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2-Bromopropane, also known as isopropyl bromide and 2-propyl bromide, is the halogenated hydrocarbon with the formula CH3CHBrCH3. It is a colorless liquid. It is used for introducing the isopropyl functional group in organic synthesis. 2-Bromopropane is prepared by heating isopropanol with hydrobromic acid.[3]

Preparation

2-Bromopropane is commercially available. It may be prepared in the ordinary manner of alkyl bromides, by reacting isopropanol with phosphorus and bromine,[4] or with phosphorus tribromide.[5]

The organomercury compound diisopropylmercury may be prepared through the magnesium-catalysed reaction of 2-bromopropane with mercuric chloride.[6]

Safety

Short-chain alkyl halides are often carcinogenic.

The bromine atom is at the secondary position, which allows the molecule to undergo dehydrohalogenation easily to give propene, which escapes as a gas and can rupture closed reaction vessels. When this reagent is used in base catalyzed reactions, potassium carbonate should be used in place of sodium or potassium hydroxide.

Further reading

  • Max Gergel, “Excuse Me Sir, Would You Like to Buy a Kilo of Isopropyl Bromide?” Pierce Chemical Co. (1979). (story of start-up chemical company).

References

  1. ^ Armarego, Wilfred L.F.; Li Lin Chai, Christina (2013). Purification of laboratory chemicals (7th ed.). Butterworth-Heinemann. p. 176. ISBN 9780123821621.
  2. ^ “2-bromopropane – Compound Summary”. PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 15 June 2012.
  3. ^ “Monograph 6526”. Merck Index of Chemicals and Drugs.
  4. ^ Oliver Kamm and C. S. Marvel (1941). “Alkyl and alkylene bromides”. Organic Syntheses; Collected Volumes, vol. 1, p. 25.
  5. ^ C. R. Noller and R. Dinsmore (1943). “Isobutyl bromide”. Organic Syntheses; Collected Volumes, vol. 2, p. 358.
  6. ^ Bailey, Philip S., ed. (1972-06-01). “The Ozonolysis of Organomercurials”. Ozone Reactions with Organic Compounds. Advances in Chemistry. Vol. 112. WASHINGTON, D. C.: AMERICAN CHEMICAL SOCIETY. pp. 78–100. doi:10.1021/ba-1972-0112.ch007. ISBN 978-0-8412-0152-1.