4-Nitrothiophenol

4-Nitrothiophenol
Names
	Other names 4-nitrobenzenethiol
Identifiers
CAS Number	1849-36-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL120606;
ChemSpider	15030;
ECHA InfoCard	100.015.852
EC Number	217-436-4;
PubChem CID	15809;
UNII	QL9H28763R;
CompTox Dashboard (EPA)	DTXSID1075145 ;
	InChI InChI=1S/C6H5NO2S/c8-7(9)5-1-3-6(10)4-2-5/h1-4,10H Key: AXBVSRMHOPMXBA-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1[N+](=O)[O-])S;
Properties
Chemical formula	C6H5NO2S
Molar mass	155.17 g·mol−1
Appearance	yellow solid
Density	1.362 g/cm3
Melting point	79–80 °C (174–176 °F; 352–353 K)
Solubility in water	alcohols
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Nitrothiophenol is an organosulfur compound with the formula HSC₆H₄NO₂. It exists as a yellow solid that is soluble in several organic solvents. It is one of three isomers of nitrothiophenol. It was originally prepared by sulfidation of 4-nitrochlorobenzene,^[1] which was improved by intentionally generating a polysulfide intermediate.^[2] 4-Nitrothiophenol is closely related to thiophenol but more acidic.

The compound reacts with chlorine to give 4-nitrophenylsulfenyl chloride, a useful reagent.^[3] It has also been used as a probe of plasmon-induced reactions.^[4]

References

^ Fromm, E.; Wittmann, J. (1908). "Derivate des p -Nitrothiophenols I. Einwirking von Schwefel und Alkali auf p-Nitrochlorobenzol". Berichte der Deutschen Chemischen Gesellschaft. 41 (2): 2264–2273. doi:10.1002/cber.190804102131.
^ Price, Charles C.; Stacy, Gardner W. (1946). "P-Nitrophenyl Disulfide, p-Nitrophenyl Sulfide and p-Nitrothiophenol¹". Journal of the American Chemical Society. 68 (3): 498–500. Bibcode:1946JAChS..68..498P. doi:10.1021/ja01207a042.
^ Kim, Sunggak (2007). "4-Nitrobenzenesulfenyl Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rn00720. ISBN 978-0-471-93623-7.
^ Sun, Mengtao; Xu, Hongxing (2012). "A Novel Application of Plasmonics: Plasmon-Driven Surface-Catalyzed Reactions". Small. 8 (18): 2777–2786. doi:10.1002/smll.201200572. PMID 22777813.

[1] Fromm, E.; Wittmann, J. (1908). "Derivate des p -Nitrothiophenols I. Einwirking von Schwefel und Alkali auf p-Nitrochlorobenzol". Berichte der Deutschen Chemischen Gesellschaft. 41 (2): 2264–2273. doi:10.1002/cber.190804102131.

[2] Price, Charles C.; Stacy, Gardner W. (1946). "P-Nitrophenyl Disulfide, p-Nitrophenyl Sulfide and p-Nitrothiophenol¹". Journal of the American Chemical Society. 68 (3): 498–500. Bibcode:1946JAChS..68..498P. doi:10.1021/ja01207a042.

[3] Kim, Sunggak (2007). "4-Nitrobenzenesulfenyl Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rn00720. ISBN 978-0-471-93623-7.

[4] Sun, Mengtao; Xu, Hongxing (2012). "A Novel Application of Plasmonics: Plasmon-Driven Surface-Catalyzed Reactions". Small. 8 (18): 2777–2786. doi:10.1002/smll.201200572. PMID 22777813.

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