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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