Triphenylmethanethiol

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Triphenylmethanethiol
Ph3CSH.png
Names
Preferred IUPAC name
Triphenylmethanethiol
Other names
Trityl mercaptan
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 223-020-3
UNII
  • InChI=1S/C19H16S/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,20H
    Key: JQZIKLPHXXBMCA-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)S
Properties
C19H16S
Molar mass 276.40 g·mol−1
Appearance yellow solid
Melting point 103–107 °C (217–225 °F; 376–380 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H332
P261, P264, P271, P280, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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[edit]

  1. ^ 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.
  2. ^ Senning, Alexander (1991). "Triphenylmethanethiol and triphenylmethanesulfenyl chloride". Sulfur Letters. 12 (4–5): 183–192.
  3. ^ 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.