Chlorocyclopropane

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 mass 76.52 g·mol−1
Density g/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 their standard state (at 25 °C [77 °F], 100 kPa).

Chlorocyclopropane is a organochlorine compound with the chemical formula C3H5Cl.[1] The compound is a member of haloalkane family.[2]

Synthesis

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

Chemical properties

The compound isomerizes on heating to 3-Chloropropene.[4] Chlorocyclopropane reacts with lithium metal in ether to produce bicyclopropane. Also, it reacts with magnesium to obtain cyclopropylmagnesium chloride.[5]

See also

References

  1. ^ "chlorocyclopropane". NIST. Retrieved 31 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. Retrieved 31 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. Retrieved 31 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. Retrieved 31 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. Retrieved 31 May 2023.

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