Bromocyclopropane Explained

Bromocyclopropane is a organobromine compound with the chemical formula .^[1] It is a member of haloalkane family.

Synthesis

The compound can be obtained by treating silver cyclopropanecarboxylate with bromine:^[2]

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.^[3]

The compound isomerizes on heating to produce 1-bromopropene and 3-bromopropene.^[4]

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.^[5]

See also

• Bromoalkanes
• Bromocyclohexane

Notes and References

1. Web site: Bromocyclopropane . . 25 May 2023.
2. Roberts . John D. . Chambers . Vaughan C. . Small-Ring Compounds. VI. Cyclopropanol, Cyclopropyl Bromide and Cyclopropylamine . . July 1951 . 73 . 7 . 3176–3179 . 10.1021/ja01151a053 . en . 0002-7863.
3. Walborsky . H. M. . Zimmermann . Christoph . The surface nature of Grignard reagent formation. Cyclopropylmagnesium bromide . . June 1992 . 114 . 13 . 4996–5000 . 10.1021/ja00039a007 . en . 0002-7863.
4. Grant . R. C. S. . Swinbourne . E. S. . The thermal isomerization of chlorocyclopropane and of bromocyclopropane . . 1 January 1966 . 17 . 620b–621 . 10.1039/C1966000620B . en . 0009-241X.
5. Web site: Bromocyclopropane, 99% . . 25 May 2023.