Chemistry:Triphenylmethanethiol
From HandWiki
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| Names | |
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| Preferred IUPAC name
Triphenylmethanethiol | |
| Other names
Trityl mercaptan
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C19H16S | |
| Molar mass | 276.40 g·mol−1 |
| Appearance | yellow solid |
| Melting point | 103–107 °C (217–225 °F; 376–380 K) |
| Hazards | |
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| GHS Signal word | Warning |
| H315, H319, H332 | |
| P261, P264, P271, P280, P302+352, P304+312, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Triphenylmethanethiol is an organosulfur compound with the formula (C6H5)3CSH. It is the thiol derivative of the bulky substituent triphenylmethyl (called trityl).[1][2]
The compound forms a number of unusual derivatives that are more stable than less bulky analogues. The sulfenyl chloride (C6H5)3CSCl is obtained from the thiol with sulfuryl chloride. It in turn reacts with ammonia to form the sulfenamide (C6H5)3CSNH2. The thiol reacts with nitrous acid to give S-nitrosotriphenylmethanethiol (C6H5)3CSNO.[3]
References
- ↑ Garnsey, Michelle R.; Wengryniuk, Sarah E.; Coltart, Don M. (2009). "Triphenylmethanethiol". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01030. ISBN 978-0471936237.
- ↑ Senning, Alexander (1991). "Triphenylmethanethiol and triphenylmethanesulfenyl chloride". Sulfur Letters 12 (4–5): 183–192.
- ↑ Arulsamy, N.; Bohle, D. S.; Butt, J. A.; Irvine, G. J.; Jordan, P. A.; Sagan, E. (1999). "Interrelationships between conformational dynamics and the redox chemistry of S-nitrosothiols". Journal of the American Chemical Society 121 (30): 7115–7123. doi:10.1021/ja9901314.
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