4171-83-9

Basic information

• Product Name: 2-NITROPHENYL PHENYL SULFIDE
• Synonyms: 2-NITROPHENYL PHENYL SULFIDE;2-NITRODIPHENYL SULFIDE;2-NITRODIPHENYL THIOETHER;1-NITRO-2-(PHENYLTHIO)BENZENE;o-Nitrophenyl phenyl sulfide;2-Nitrodiphenyl thioether 98%;2-NITRO DIPHENYL SULFIDE 99%MIN;(2-nitrophenyl)(phenyl)sulfane
• CAS NO: 4171-83-9
• Molecular Formula: C₁₂H₉NO₂S
• Molecular Weight: 231.27
• Mol File: 4171-83-9.mol
• Article Data: 77

Chemical Properties

• Melting Point: 78-82 °C(lit.)
• Boiling Point: 343.3 °C at 760 mmHg
• Flash Point: 161.4 °C
• Appearance: Pale yellow crystal
• Density: 1.2840 (rough estimate)
• Vapor Pressure: 0.000141mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: 2-NITROPHENYL PHENYL SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROPHENYL PHENYL SULFIDE(4171-83-9)
• EPA Substance Registry System: 2-NITROPHENYL PHENYL SULFIDE(4171-83-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4171-83-9(Hazardous Substances Data)

Usage

Uses

2-Nitrophenyl Phenyl Sulfide is used in the study of non-nucleoside reverse transcriptase inhibitors of HIV-1.

Synthesis Reference(s)

Synthetic Communications, 16, p. 1335, 1986 DOI: 10.1080/00397918608056380

InChI:InChI=1/C12H9NO2S/c14-13(15)11-8-4-5-9-12(11)16-10-6-2-1-3-7-10/h1-9H

Upstream product

• 64-17-5 ethanol 
• 577-19-5 2-nitrophenyl bromide 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 88-73-3 2-Chloronitrobenzene 
• 52599-08-3 o-Nitrobenzoldiazophenylsulfid 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 3111-52-2 potassium thiophenolate 
• 882-33-7 diphenyldisulfane 
• 4875-10-9 o-nitrothiophenol 
• 108-90-7 chlorobenzene 
• 1226-48-8 2-nitrophenyl p-toluenesulphonate 
• 528-29-0 1,2-Dinitrobenzene 
• 1155-00-6 bis(2-nitrophenyl)disulfide 

Downstream Products

• 6764-13-2 2-aminodiphenyl sulfide hydrochloride 
• 90158-92-2 N,N'-Bis-(2-phenylsulfanyl-phenyl)-diazene N-oxide 
• 141691-24-9 2-Phenylthiophenylhydroxylamine 
• 108-98-5 thiophenol 
• 88-74-4 2-nitro-aniline 
• 88-75-5 2-hydroxynitrobenzene 
• 54615-61-1 S-(2-nitrophenyl)-S-phenylsulfilimine 

Relevant articles and documents

Synthesis of N-allyl and N-acyl-2-vinylindoline

Heating a mixture of (2R*,3R*)- and (2R*,3S*)-2- [(1S*)-1-iodoethyl]-3,5-dimethyl-1-[(2-nitrophenyl) sulfonyl]indolines with N-isopropylpiperidine in xylene resulted in (2S*,3R*)-3,5- dimethyl-1-[(2-nitrophenyl) sulfonyl]-2-vinylindoline. The latter reacted with thiophenol to afford (2S*,3R*)-3,5-dimethyl-2-vinylindoline, whose reaction with allyl halides or acetyl bromide gave rise to N-allyl-, N-propenyl-, or N-acetyl derivatives. Nitration of 1-acetyl-3,5-dimethyl-2- vinylindoline yielded ortho-nitro derivative.

Synthesis of thioethers, arenes and arylated benzoxazoles by transformation of the C(aryl)-C bond of aryl alcohols

Transformation of aryl alcohols into high-value functionalized aromatic compounds by selective cleavage and functionalization of the C(aryl)-C(OH) bond is of crucial importance, but very challenging by far. Herein, for the first time, we report a novel and versatile strategy for activation and functionalization of C(aryl)-C(OH) bonds by the cooperation of oxygenation and decarboxylative functionalization. A diverse range of aryl alcohol substrates were employed as arylation reagents via the cleavage of C(aryl)-C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant. This study offers a new way for aryl alcohol conversion and potentially offers a new opportunity to produce high-value functionalized aromatics from renewable feedstocks such as lignin which features abundant C(aryl)-C(OH) bonds in its linkages.

An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols

A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C-S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.