Chlorocarbonylsulfenyl chloride
Chemical compound
From Wikipedia, the free encyclopedia
Chlorocarbonylsulfenyl chloride is the chemical compound with the formula ClâC(=O)âSâCl. It is a colorless, distillable liquid that is related to phosgene. It features two reactive functional groups, an acyl chloride and a sulfenyl chloride. According to X-ray crystallography, the molecule is planar.[1]
sulfenyl_chloride.svg) | |
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| Properties | |
| ClâC(=O)âSâCl | |
| Molar mass | 130.97 g·molâ1 |
| Appearance | colorless liquid |
| Density | 1.552 g/cm3 |
| Boiling point | 98 °C (208 °F; 371 K) |
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| Danger | |
| H314 | |
| P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and reactions
Chlorocarbonylsulfenyl chloride is prepared by hydrolysis of trichloromethane sulfenyl chloride in sulfuric acid as solvent:[2]
- Cl3CâSâCl + H2O â ClâSâC(=O)âCl + 2 HCl
The compound, being bifunctional, has been used for the preparation of several heterocycles including oxathiazol-2-ones, oxathialones, and oxathiazoles.[3]
Treatment with formamides gives dithiazolidinediones (also known as dithiasuccinoyl, or DTS).[4]
Relevant to amino acid chemistry, ethylthionocarbamates react with chlorocarbonylsulfenyl chloride to give DTS derivatives:[5][6]