Chemistry:2-Bromopentane

From HandWiki

2-Bromopentane is a bromoalkane and isomer of bromopentane. It is a colorless liquid. 2-Bromopentane is chiral and thus can be obtained as either of two stereoisomers designated as (R)-2-bromopentane and (S)-2-bromopentane, or as a racemic 1:1 mixture of the two enantiomers.

Applications

2-Bromopentane is an organic synthetic compound that can be used in cross-coupling reactions.[1] It is also used as an intermediate in organic synthesis.[2]

Synthesis

2-Bromopentane, along with 3-bromopentane, may be produced by the bromination of 2-pentanol. This has historically been performed using hydrogen bromide gas, aqueous sulfuric and hydrobromic acid mixtures, and phosphorus tribromide.[3]

References

  1. Cahiez, Gérard; Moyeux, Alban (2010-03-10). "Cobalt-Catalyzed Cross-Coupling Reactions" (in en). Chemical Reviews 110 (3): 1435–1462. doi:10.1021/cr9000786. ISSN 0009-2665. https://pubs.acs.org/doi/10.1021/cr9000786. 
  2. Ekpa, O.; Wheeler, J.W.; Cokendolpher, J.C.; Duffield, R.M. (1985). "Ketones and alcohols in the defensive secretion of Leiobunum townsendi weed and a review of the known exocrine secretions of Palpatores (Arachnida:Opiliones)" (in en). Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 81 (3): 555–557. doi:10.1016/0305-0491(85)90365-7. https://linkinghub.elsevier.com/retrieve/pii/0305049185903657. 
  3. Howell, B. A.; Kohrman, R. E. (October 1984). "Preparation of 2-Bromopentane". Journal of Chemical Education 61 (10). doi:10.1021/ed061p932. https://pubs.acs.org/doi/pdf/10.1021/ed061p932.