organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, 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.Clay ...

, 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 res ...

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 Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, es ...

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 consid ...

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 carbo ...

References

Acyl chlorides Functional groups Organosulfur compounds