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Thiophosgene is a yellow liquid with the formula CSCl2. This compound has a trigonal planar geometry. It possesses two reactive C-Cl bonds that allow this reagent to be used in diverse procedures related to organic synthesis.
Additional recommended knowledge
Synthesis of CSCl2
CSCl2 is prepared in a two-step process from carbon disulfide. In the first step, carbon disulfide is chlorinated to give trichloromethanesulfenyl chloride, CCl3SCl:
The chlorination must be controlled as excess chlorine converts trichloromethanesulfenyl chloride into carbon tetrachloride. Steam distillation separates the trichloromethanesulfenyl chloride, a rare sulfenyl chloride, and hydrolyzes the sulfur monochloride. Reduction of trichloromethanesulfenyl chloride produces thiophosgene:
Typically, tin is used for the reducing agent M.
Uses of CSCl2
CSCl2 is mainly used to prepare compounds with the connectivity CSX2 where X = OR, NHR. Such reactions proceed via intermediate such as CSClX. Under certain conditions, one can convert primary amines into isothiocyanates. CSCl2 also serves as a dienophile to give, after reduction 5-thiacyclohexene derivatives.
CSCl2 is considered highly toxic.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Thiophosgene". A list of authors is available in Wikipedia.|