4-Nitrothiophenol

4-Nitrothiophenol

Names
Preferred IUPAC name 4-Nitrobenzene-1-thiol
Other names 4-nitrobenzenethiol
Identifiers
CAS Number	1849-36-1  Y
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:
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

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.