organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, ...

, thioacyl chloride is a

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the re ...

of the type RC(S)Cl, where R is an organic substituent. Thioacyl chlorides are analogous to acid chlorides, but much rarer and less robust. The best studied is thiobenzoyl chloride, a purple oil first prepared by chlorination of dithiobenzoic acid with a combination of chlorine and

thionyl chloride Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year bein ...

. A more modern preparation employs phosgene as the chlorinating agent,{{cite journal, doi= 10.1002/zfch.19750150904, authors=Viola, H.;Mayer, R., journal=Z. Chem., title=Eine neue Darstellungsmethode für aromatische Thiocarbonsäurechloride, trans-title=A New Preparation Route for Aromatic Thiocarboxylic Acid Chlorides, year=1975, volume=15, issue=9, page=348 this also generates

carbonyl sulfide Carbonyl sulfide is the chemical compound with the linear formula OCS. It is a colorless flammable gas with an unpleasant odor. It is a linear molecule consisting of a carbonyl group double bonded to a sulfur atom. Carbonyl sulfide can be consi ...

as a by-product. PhCS₂H + COCl₂ → PhC(S)Cl + HCl + COS The most common thioacyl chloride is

thiophosgene Thiophosgene is a red liquid with the formula . It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses. Preparation is prepared in a two-step process from carbon ...

References

Acyl chlorides Functional groups Organosulfur compounds