Mercaptobenzothiazole
thiazole-2-thiol_200.svg) |
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IUPAC name
1,3-Benzothiazole-2(3H)-thione
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3D model (Jmol)
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| ECHA InfoCard | 100.005.216 |
| EC Number | 205-736-8 |
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PubChem CID
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| Properties | |
| C7H5NS2 | |
| Molar mass | 167.25 |
| Appearance | solid |
| Melting point | 177-181 °C |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
2-Mercaptobenzothiazole (MBT) is an organosulfur compound with the formula C6H4NSCSH. The molecule consists of a benzene ring fused to a 2-mercaptothiazole ring. It is used in the vulcanization of rubber.
It is produced by the reaction of 2-aminothiophenol and carbon disulfide:
It oxidizes to give the disulfide called MBTS. Upon oxidation in the presence of secondary amines, it gives sulfenamide derivatives. One commercially useful example is 2-morpholinodithiobenzothiazole (MBSS), which is used as an accelerator in the vulcanization of rubber.
Using MBT, rubber vulcanizes with less sulfur and at milder temperatures, both factors give a stronger product. This effect was reported in 1921 by workers at Pirelli and at Goodyear Tire & Rubber.
This compound is used as cooling tower biocide.
The compound has also been used in the past in the gold-mining industry to "float" the gold from ore residue as part of the extraction process.
Studies have identified it as a potiential human carcinogen. In 2016, it was identified by the World Health Organization as a human carcinogen.
It causes allergic contact dermatitis. The derivative morpholinylmercaptobenzothiazole is a reported allergen in protective gloves, including latex, nitrile, and neoprene gloves.
It becomes air-borne as a result of wear on car tires, and is able to be inhaled.
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