701-57-5

Basic information

• Product Name: 4-NITROTHIOANISOLE
• Synonyms: methyl(4-nitrophenyl)sulfane;p-Nitrophenyl methyl sulfide;1-Nitro-4-(methylthio)benzene;Methyl 4-nitrophenyl sulphide, 1-(Methylsulphanyl)-4-nitrobenzene, 4-(Methylthio)nitrobenzene;4-(METHYLTHIO)NITROBENZENE;4-NITROTHIOANISOLE;1-(METHYLTHIO)-4-NITROBENZENE;METHYL-4-NITROPHENYL SULFIDE
• CAS NO: 701-57-5
• Molecular Formula: C₇H₇NO₂S
• Molecular Weight: 169.2
• EINECS: 1312995-182-4
• Mol File: 701-57-5.mol
• Article Data: 82

Chemical Properties

• Melting Point: 66-69 °C(lit.)
• Boiling Point: 140 °C / 2mmHg
• Flash Point: 128.8 °C
• Appearance: Light yellow to brown solid
• Density: 1.2391
• Vapor Pressure: 0.00384mmHg at 25°C
• Refractive Index: 1.6401 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• Sensitive: Stench
• BRN: 1817928
• CAS DataBase Reference: 4-NITROTHIOANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROTHIOANISOLE(701-57-5)
• EPA Substance Registry System: 4-NITROTHIOANISOLE(701-57-5)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22
• Safety Statements: 22-36/37/39-36/37
• WGK Germany: 3
• HazardClass: IRRITANT, STENCH
• Hazardous Substances Data: 701-57-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

Uses

4-Nitrothioanisole may be used to synthesize 4-nitrothioanisole sulfoxide and methyl 4-nitrophenyl sulfoxide.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 2575, 1983 DOI: 10.1016/S0040-4039(00)81985-1

General Description

4-Nitrothioanisole in acetone-d6 solution exhibits twofold barrier to rotation about the Csp2-S bond as 16.1±1.5kJ/mol. 4-Nitrothioanisole undergoes hydrogenation in the presence of sulfided Pd/C catalysts.

InChI:InChI=1/C7H7NO2S/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3

Upstream product

• 624-92-0 Dimethyldisulphide 
• 24067-17-2 4-nitrophenylboronic acid 
• 616-38-6 carbonic acid dimethyl ester 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 35371-03-0 4-iodothioanisole 
• 350-46-9 4-Fluoronitrobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 56075-39-9 1-(methylsulfonyl)-2-(4-nitrophenyl)diazene 
• 867-44-7 S-Methylisothiourea sulfate 
• 110-05-4 di-tert-butyl peroxide 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 940-12-5 p-nitrophenyl methyl sulfoxide 

Downstream Products

• 38947-36-3 4,4'-dimethylthioazoxybenzene 
• 861569-50-8 N,N'-bis-(4-methylsulfanyl-phenyl)-hydrazine 
• 940-12-5 p-nitrophenyl methyl sulfoxide 
• 64-19-7 acetic acid 
• 940-12-5 (S)-methyl 4-nitrophenyl sulfoxide 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 1251955-02-8 S-methyl-S-(4-nitrophenyl)-N-(trifluoromethanesulfonyl)sulfilimine 
• 1323993-89-0 (+/-)-2-[(p-nitrophenylsulfinyl)methyl]chroman-2-ol 
• 1323994-01-9 C₁₆H₁₅NO₅S 
• 15436-27-8 S-methyl-S-(4-nitrophenyl)-N-(p-tolylsulfonyl)sulfimide 
• 15436-27-8 S-methyl-S-(4-nitrophenyl)-N-(p-tolylsulfonyl)sulfimide 
• 946826-92-2 N-(cyano)4-nitrophenyl methyl sulfilimine 
• 170288-29-6 N-(4-(methylthio)phenyl)formamide 

Relevant articles and documents

A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction

In this work, we have explored how the confinement of the protic ionic liquid (IL) ethylammonium nitrate (EAN) inside toluene/benzyl-n-hexadecyldimethylammonium chloride (BHDC) reverse micelles (RMs) affects the Cl- nucleophilicity on the bimolecular nucleophilic substitution (SN2) reaction between this anion and dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate. To the best of our knowledge this is the first report where toluene/BHDC RMs use EAN as a polar component and it is used as a nanoreactor for carrying out kinetic experiments. Dynamic light scattering results reveal the formation of RMs containing the protic IL. The kinetic results show that upon confinement, EAN becomes a suitable solvent for the SN2 reaction while in homogeneous media it is a bad option. Entrapped in BHDC RMs, due to the strong hydrogen bond interactions, EAN behaves as an aprotic-like IL which cannot deactivate the nucleophilic power of Cl- and yet increases the substrate solubility. These facts show the versatility of this kind of organized system to alter the polar solvent entrapped and its influence on the reaction rate when it is used as a nanoreactor.

Synthesis of Aryl Methyl Sulfides from Arysulfonyl Chlorides with Dimethyl Carbonate as the Solvent and C1 Source

A new procedure for the synthesis of aryl methyl sulfides from dimethyl carbonate (DMC) and arylsulfonyl chlorides has been achieved. In this strategy, DMC plays a dual role as both, C1 building block and green solvent. Arylsulfonyl chlorides served as the sulfur precursors, and a variety of aryl methyl sulfides were obtained in moderate to excellent yields with good functional group tolerance. Additionally, alkylsulfonyl chloride and dibenzyl carbonate are proven to be suitable substrates as well.

t-BuOK-promoted methylthiolation of aryl fluorides with dimethyldisulfide under transition-metal-free and mild conditions

In the presence of potassium tert-butoxide (t-BuOK), the cross-coupling reaction between aryl fluorides and dimethyldisulfide was developed. A series of aryl methyl sulfides were obtained in moderate to good yields under transition-metal-free and mild conditions.

Copper-Catalyzed Methylthiolation of Aryl Iodides and Bromides with Dimethyl Disulfide in Water

An efficient route to aryl methyl sulfides through the copper-catalyzed coupling reaction of aryl iodides or bromides with dimethyl disulfide in water is described. Electron-donating and electron-withdrawing functional groups in the substrates were tolerated, and the corresponding products were obtained in moderate to good yields.