Misplaced Pages

Tetrachlorocyclopropene

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Tetrachlorocyclopropene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.025.835 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3Cl4/c4-1-2(5)3(1,6)7Key: BLZOHTXDDOAASQ-UHFFFAOYSA-N
SMILES
  • ClC1=C(Cl)C1(Cl)Cl
Properties
Chemical formula C3Cl4
Molar mass 177.83 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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. It is prepared by addition of dichlorocarbene to trichloroethylene. It can react with water and alcohols rapidly.

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. S2CID 96607067.
  3. Pentachlorocyclopropane Stephen W. Tobey and Robert West. The University of Wisconsin (1965)
Categories: