4-Nitrothiophenol: Difference between revisions

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	{{Chembox		{{Chembox
	\| ImageFile =		\| ImageFile = 4HSC6H4NO2.svg
	\| ImageSize =		\| ImageSize = 70
	\| ImageAlt =		\| ImageAlt =
	\| IUPACName =		\| IUPACName =
	\| OtherNames =		\| OtherNames = 4-nitrobenzenethiol
	\|Section1={{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| CASNo = 1849-36-1		\| CASNo = 1849-36-1
			\| CASNo_Ref = {{Cascite\|correct\|CAS}}
	\| CASNo_Comment =
	\| ~~CASNo1~~ =		\| ChEMBL = 120606
	\| ~~CASNo1_Comment~~ =		\| ChemSpiderID = 15030
	\| ~~PubChem~~ =		\| EC_number = 217-436-4
	\| ~~SMILES~~ = }}		\| PubChem = 15809
			\| UNII = QL9H28763R
			\| StdInChI=1S/C6H5NO2S/c8-7(9)5-1-3-6(10)4-2-5/h1-4,10H
			\| StdInChIKey = AXBVSRMHOPMXBA-UHFFFAOYSA-N
			\| SMILES = C1=CC(=CC=C1(=O))S
			}}
	\|Section2={{Chembox Properties		\|Section2={{Chembox Properties
	\| C=6\|H=5\|S=1\|N=1\|O=2		\| C=6\|H=5\|S=1\|N=1\|O=2
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	\| BoilingPt =		\| BoilingPt =
	\| BoilingPt_notes =		\| BoilingPt_notes =
	\| Solubility = }}		\| Solubility = alcohols}}
	\|Section3={{Chembox Hazards		\|Section3={{Chembox Hazards
			\| GHS_ref=
			\| GHSPictograms = {{GHS07}}
			\| GHSSignalWord = Warning
			\| HPhrases = {{H-phrases\|315\|319\|335}}
			\| PPhrases = {{P-phrases\|261\|264\|264+265\|271\|280\|302+352\|304+340\|305+351+338\|319\|321\|332+317\|337+317\|362+364\|403+233\|405\|501}}
	\| MainHazards =		\| MainHazards =
	\| FlashPt =		\| FlashPt =
	\| AutoignitionPt = }}		\| AutoignitionPt = }}
	}}		}}
	'''4-Nitrothiophenol''' is an ] with the formula {{chem2\|HSC6H4NO2}}. It exists as a yellow solid that is soluble in several organic solvent]]s. ~~The compound~~ is one of three isomers of nitrothiophenol. It was originally prepared by sulfidation of ].<ref>{{cite journal \|doi=10.1002/cber.190804102131 \|title=Derivate des ''p'' -Nitrothiophenols \|date=1908 \|last1=Fromm \|first1=E. \|last2=Wittmann \|first2=J. \|journal=Berichte der Deutschen Chemischen Gesellschaft \|volume=41 \|issue=2 \|pages=2264–2273 }}</ref>		'''4-Nitrothiophenol''' is an ] with the formula {{chem2\|HSC6H4NO2}}. It exists as a yellow solid that is soluble in several ]s. It is one of three isomers of nitrothiophenol. It was originally prepared by sulfidation of ],<ref>{{cite journal \|doi=10.1002/cber.190804102131 \|title=Derivate des ''p'' -Nitrothiophenols I. Einwirking von Schwefel und Alkali auf p-Nitrochlorobenzol \|date=1908 \|last1=Fromm \|first1=E. \|last2=Wittmann \|first2=J. \|journal=Berichte der Deutschen Chemischen Gesellschaft \|volume=41 \|issue=2 \|pages=2264–2273 }}</ref> which was improved by intentionally generating a polysulfide intermediate.<ref>{{cite journal \|doi=10.1021/ja01207a042 \|title=P-Nitrophenyl Disulfide, p-Nitrophenyl Sulfide and ''p''-Nitrothiophenol<sup>1</sup> \|date=1946 \|last1=Price \|first1=Charles C. \|last2=Stacy \|first2=Gardner W. \|journal=Journal of the American Chemical Society \|volume=68 \|issue=3 \|pages=498–500 \|bibcode=1946JAChS..68..498P }}</ref> 4-Nitrothiophenol is closely related to ] but more acidic.

	The compound reacts with chlorine to give 4-nitrophenyl], a useful reagent.<ref>{{cite book \|doi=10.1002/9780470842898.rn00720 \|chapter=4-Nitrobenzenesulfenyl Chloride \|title=Encyclopedia of Reagents for Organic Synthesis \|date=2007 \|last1=Kim \|first1=Sunggak \|isbn=978-0-471-93623-7 }}</ref> It has also been used as a probe of ]-induced reactions.<ref>{{cite journal\|doi=10.1002/smll.201200572 \|title=A Novel Application of Plasmonics: Plasmon-Driven Surface-Catalyzed Reactions \|date=2012 \|last1=Sun \|first1=Mengtao \|last2=Xu \|first2=Hongxing \|journal=Small \|volume=8 \|issue=18 \|pages=2777–2786 \|pmid=22777813 }}</ref>		The compound reacts with chlorine to give 4-nitrophenyl], a useful reagent.<ref>{{cite book \|doi=10.1002/9780470842898.rn00720 \|chapter=4-Nitrobenzenesulfenyl Chloride \|title=Encyclopedia of Reagents for Organic Synthesis \|date=2007 \|last1=Kim \|first1=Sunggak \|isbn=978-0-471-93623-7 }}</ref> It has also been used as a probe of ]-induced reactions.<ref>{{cite journal\|doi=10.1002/smll.201200572 \|title=A Novel Application of Plasmonics: Plasmon-Driven Surface-Catalyzed Reactions \|date=2012 \|last1=Sun \|first1=Mengtao \|last2=Xu \|first2=Hongxing \|journal=Small \|volume=8 \|issue=18 \|pages=2777–2786 \|pmid=22777813 }}</ref>
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	]		]
			]

Latest revision as of 08:07, 20 January 2025

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/h1-4,10HKey: 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
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

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-Nitrothiophenol". 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.

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