Bromocyclopropane

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

Bromocyclopropane
Names
Preferred IUPAC name
Bromocyclopropane
Other names
Cyclopropyl bromide, cyclopropylbromide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.160
EC Number
  • 224-375-7
  • InChI=1S/C3H5Br/c4-3-1-2-3/h3H,1-2H2
    Key: LKXYJYDRLBPHRS-UHFFFAOYSA-N
  • C1CC1Br
Properties
C3H5Br
Molar mass 120.977 g·mol−1
Appearance liquid
Density 1.515 g/cm3
Boiling point 68–70 °C (154–158 °F; 341–343 K)
Insoluble
Hazards
GHS labelling:[1]
GHS02: FlammableGHS07: Exclamation mark
Danger
H225, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501
Related compounds
Related compounds
 Chlorocyclopropane
Fluorocyclopropane
Iodocyclopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.
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