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Bromocyclopropane is a organobromine compound with the chemical formula C3H5Br.[2] It is a member of haloalkane family.

Synthesis

The compound can be obtained by treating silver cyclopropanecarboxylate with bromine:[3]

C3H5CO2Ag + Br2 → C3H5Br + AgBr + CO2

Chemical properties

Reaction with magnesium, using diethyl ether as solvent, only gives about 25–30% of the cyclopropylmagnesium bromide Grignard reagent, with nearly as much cyclopropane formed by alternate reactions on the metal surface.[4]

The compound isomerizes on heating to produce 1-bromopropene and 3-bromopropene.[5]

Physical properties

The compound is a flammable liquid that causes skin irritation and serious eye irritation. It is soluble in chloroform and methanol. Insoluble in water.[6]

See also

References

  1. ^ “Bromocyclopropane”. pubchem.ncbi.nlm.nih.gov.
  2. ^ “Bromocyclopropane”. Sigma Aldrich. Retrieved 25 May 2023.
  3. ^ Roberts, John D.; Chambers, Vaughan C. (July 1951). “Small-Ring Compounds. VI. Cyclopropanol, Cyclopropyl Bromide and Cyclopropylamine”. Journal of the American Chemical Society. 73 (7): 3176–3179. doi:10.1021/ja01151a053. ISSN 0002-7863.
  4. ^ Walborsky, H. M.; Zimmermann, Christoph (June 1992). “The surface nature of Grignard reagent formation. Cyclopropylmagnesium bromide”. Journal of the American Chemical Society. 114 (13): 4996–5000. doi:10.1021/ja00039a007. ISSN 0002-7863.
  5. ^ Grant, R. C. S.; Swinbourne, E. S. (1 January 1966). “The thermal isomerization of chlorocyclopropane and of bromocyclopropane”. Chemical Communications (17): 620b–621. doi:10.1039/C1966000620B. ISSN 0009-241X.
  6. ^ “Bromocyclopropane, 99%”. Alfa Aesar. Retrieved 25 May 2023.