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4-Nitrothiophenol

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4-Nitrothiophenol
Names
Other names 4-nitrobenzenethiol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.015.852 Edit this at Wikidata
EC Number
  • 217-436-4
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H5NO2S/c8-7(9)5-1-3-6(10)4-2-5/h1-4,10HKey: AXBVSRMHOPMXBA-UHFFFAOYSA-N
SMILES
  • C1=CC(=CC=C1(=O))S
Properties
Chemical formula C6H5NO2S
Molar mass 155.17 g·mol
Appearance yellow solid
Density 1.362 g/cm
Melting point 79–80 °C (174–176 °F; 352–353 K)
Solubility in water alcohols
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
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 , 100 kPa). Infobox references
Chemical compound

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, which was improved by intentionally generating a polysulfide intermediate. 4-Nitrothiophenol is closely related to thiophenol but more acidic.

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

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-Nitrothiophenol". 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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