Triphenylmethanethiol

Triphenylmethanethiol
Names
	Preferred IUPAC name Triphenylmethanethiol
	Other names Trityl mercaptan
Identifiers
CAS Number	3695-77-0;
3D model (JSmol)	Interactive image;
ChemSpider	69703;
ECHA InfoCard	100.020.928
EC Number	223-020-3;
PubChem CID	77281;
UNII	T7AQN86QSJ ;
CompTox Dashboard (EPA)	DTXSID1063142 ;
	InChI 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;
	SMILES C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)S;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H332
Precautionary statements	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). 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.

[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.

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