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Bromocyclopropane

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(Redirected from Cyclopropyl bromide)
Bromocyclopropane
Names
Preferred IUPAC name Bromocyclopropane
Other names Cyclopropyl bromide, cyclopropylbromide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.160 Edit this at Wikidata
EC Number
  • 224-375-7
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H5Br/c4-3-1-2-3/h3H,1-2H2Key: LKXYJYDRLBPHRS-UHFFFAOYSA-N
SMILES
  • C1CC1Br
Properties
Chemical formula C3H5Br
Molar mass 120.977 g·mol
Appearance liquid
Density 1.515 g/cm
Boiling point 68–70 °C (154–158 °F; 341–343 K)
Solubility in water Insoluble
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation mark
Signal word Danger
Hazard statements H225, H315, H319, H335
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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

Synthesis

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

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.

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

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.

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.
Bromine compounds
Br(−I)
Br(−I,I)
Br(I)
Br(II)
Br(I,V)
Br(III)
Br(IV)
Br(V)
Br(VII)
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