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Chlorocyclopropane

From Wikipedia, the free encyclopedia
Chlorocyclopropane
Names
Preferred IUPAC name
Chlorocyclopropane
Other names
Cyclopropyl chloride, cyclopropylchloride
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 230-988-0
UNII
  • InChI=1S/C3H5Cl/c4-3-1-2-3/h3H,1-2H2
    Key: VEZNCHDBSQWUHQ-UHFFFAOYSA-N
  • C1CC1Cl
Properties
C3H5Cl
Molar mass76.52 g·mol−1
Densityg/cm3
Melting point−97.68 °C (−143.82 °F; 175.47 K)
Related compounds
Related compounds
Fluorocyclopropane
Bromocyclopropane
Iodocyclopropane
Pentachlorocyclopropane
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Chlorocyclopropane is aorganochlorine compound with the chemical formulaC3H5Cl.[1] The compound is a member ofhaloalkane family.[2]

Synthesis

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The compound can be obtained by photoreaction ofcyclopropane and chlorine gas; the reaction will generate polychlorinated compounds, which can be separated by physical means.[3]

Chemical properties

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The compound isomerizes on heating to3-Chloropropene.[4] Chlorocyclopropane reacts withlithium metal in ether to produce bicyclopropane. Also, it reacts with magnesium to obtain cyclopropylmagnesium chloride.[5]

See also

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References

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  1. ^"chlorocyclopropane".NIST. Retrieved31 May 2023.
  2. ^Murin, A. N.; Murin, I. V.; Kazakov, V. P.; Sivkov, V. P. (1 May 1972)."NQR study of the nature of C-C1 bonds in chlorocyclopropanes".Journal of Structural Chemistry.13 (3):497–500.doi:10.1007/BF00743850.ISSN 1573-8779.S2CID 94857888. Retrieved31 May 2023.
  3. ^Slabey, Vernon A. (October 1952)."Reaction of Cyclopropyl Chloride with Lithium. Isolation of Dicyclopropyl".Journal of the American Chemical Society.74 (19):4928–4930.doi:10.1021/ja01139a056.ISSN 0002-7863. Retrieved31 May 2023.
  4. ^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. Retrieved31 May 2023.
  5. ^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. Retrieved31 May 2023.
Chlorides andacids
Chlorine fluorides
Chlorine oxides
Chlorineoxyfluorides
Chlorine(I) derivatives
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