Tetrachlorocyclopropene

Tetrachlorocyclopropene
Identifiers
CAS Number	6262-42-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	72642;
ECHA InfoCard	100.025.835
PubChem CID	80428;
UNII	4161QF853X ;
CompTox Dashboard (EPA)	DTXSID6021660 ;
	InChI InChI=1S/C3Cl4/c4-1-2(5)3(1,6)7 Key: BLZOHTXDDOAASQ-UHFFFAOYSA-N;
	SMILES ClC1=C(Cl)C1(Cl)Cl;
Properties
Chemical formula	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

^ Oliver Reiser; Armin de Meijere (2001). "Tetrachlorocyclopropene". EEROS. doi:10.1002/047084289X.rt028. ISBN 0-471-93623-5.
^ 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.
^ Pentachlorocyclopropane Stephen W. Tobey and Robert West. The University of Wisconsin (1965)

[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)

[1]

[2]

[3]