Tetrachlorocyclopropene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.025.835
UNII
  • InChI=1S/C3Cl4/c4-1-2(5)3(1,6)7
    Key: BLZOHTXDDOAASQ-UHFFFAOYSA-N
  • ClC1=C(Cl)C1(Cl)Cl
Properties
C3Cl4
Molar mass 177.83 g·mol−1
Appearance Colorless liquid
Density 1.45 g/mL
Boiling point 125 - 130 C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetrachlorocyclopropene is a chemical compound with the formula C3Cl4. A colorless liquid, the compound is a reagent used to prepare acetylene derivatives and in organic synthesis.[1] It is prepared by addition of dichlorocarbene to trichloroethylene.[2] It can react with water and alcohols rapidly.[3]

The compound is used to prepare arylpropiolic acids:

C3Cl4 + ArH + 2 H2O → ArC2CO2H + 4 HCl

Under some circumstances, diarylation occurs, giving diarylcyclopropenones, which decarbonylate to give diarylacetylenes. These reactions are thought to proceed via the intermediacy of trichlorocyclopropenium electrophile (C3Cl3+).

References

  1. ↑ Oliver Reiser; Armin de Meijere (2001). "Tetrachlorocyclopropene". EEROS. doi:10.1002/047084289X.rt028. ISBN 0-471-93623-5.
  2. ↑ Glück, C; Poingée, V; Schwager, H (1987). "Improved Synthesis of 7,7-Difluorocyclopropabenzene". Synthesis. 1987 (3): 260–262. doi:10.1055/s-1987-27908.
  3. ↑ Pentachlorocyclopropane Stephen W. Tobey and Robert West. The University of Wisconsin (1965)
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