2524-76-7

Basic information

• Product Name: 3-NITRO THIOANISOLE
• Synonyms: METHYL 3-NITROPHENYL SULFIDE;3-NITRO THIOANISOLE;3-NITRO THIOANSOLE;1-(methylthio)-3-nitrobenzene;3-NITROTHIOANISOLE / METHYL 3-NITROPHENYL SULPHIDE;3-NITRO THIOANISOLE 98%MIN;BENZENE,1-(METHYLTHIO)-3-NITRO;1-Nitro-3-(methylthio)benzene
• CAS NO: 2524-76-7
• Molecular Formula: C₇H₇NO₂S
• Molecular Weight: 169.2
• EINECS: 219-761-7
• Mol File: 2524-76-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 14 °C
• Boiling Point: 92 °C / 1mmHg
• Flash Point: 112.6°C
• Appearance: /
• Density: 1.29
• Vapor Pressure: 0.0176mmHg at 25°C
• Refractive Index: 1.6160 to 1.6200
• CAS DataBase Reference: 3-NITRO THIOANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NITRO THIOANISOLE(2524-76-7)
• EPA Substance Registry System: 3-NITRO THIOANISOLE(2524-76-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT, STENCH
• Hazardous Substances Data: 2524-76-7(Hazardous Substances Data)

Usage

General Description

3-NITRO THIOANISOLE is a chemical compound with the molecular formula C7H7NO3S. It is a nitro aromatic compound that consists of a benzene ring with a nitro group and a thioether group attached. It is commonly used in organic synthesis as a reagent in the preparation of various organic compounds. 3-NITRO THIOANISOLE has potential applications as a precursor to dyes, pharmaceuticals, and agrochemicals, and it also has uses in the production of polymers and materials. It is important to handle and use this compound with care, as it is flammable and may be harmful if inhaled or ingested.

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

Upstream product

• 16671-77-5 3-nitrophenyl thiocyanate 
• 537-91-7 bis(3-nitrophenyl) disulfide 
• 5188-07-8 sodium thiomethoxide 
• 624-92-0 Dimethyldisulphide 
• 99-09-2 3-nitro-aniline 
• 3814-18-4 3-nitrothiophenol 
• 77-78-1 dimethyl sulfate 
• 13511-86-9 S-(3-nitrophenyl) dimethylthiocarbamate 
• 16278-29-8 3-nitrobenzenediazonium 
• 99-65-0 meta-dinitrobenzene 
• 3908-55-2 Trimethyl(methylthio)silane 
• 1783-81-9 3-methylmercaptoaniline 
• 13331-27-6 m-nitrobenzene boronic acid 
• 121-73-3 3-Nitrochlorobenzene 

Downstream Products

• 857586-50-6 bis-(3-methylsulfanyl-phenyl)-diazene-N-oxide 
• 857586-90-4 bis-(3-methylsulfanyl-phenyl)-diazene 
• 132016-29-6 methyl 3-nitrophenyl sulfoxide 
• 90109-81-2 (3-nitro-phenyl)-trichloromethyl sulfide 
• 13118-31-5 dimethyl-(3-nitro-phenyl)-sulfonium ; methyl sulfate 
• 132016-29-6 (+)-(S)-3-methylsulfinylnitrobenzene 
• 146143-21-7 (+)-(R)-3-methylsulfinylnitrobenzene 
• 1657-86-9 (2,4-dinitro-phenyl)-(3-nitro-phenyl)-sulfide 
• 1783-81-9 3-methylmercaptoaniline 
• 64-19-7 acetic acid 
• 23153-09-5 1-amino-4-methylthio-2-nitrobenzene 
• 494226-39-0 6-(methylsulfanyl)-2-nitroaniline 
• 107518-44-5 (3-methylsulfanyl-phenyl)-phenyl-diazene 
• 370-47-8 (3-nitrophenyl)(trifluoromethyl)sulfane 

Relevant articles and documents

Continuous-Flow Process for the Synthesis of m-Nitrothioanisole

A continuous-flow process for the preparation of m-nitrothioanisole has been set up. The starting material m-nitroaniline was diazotized to give diazonium chloride, followed by azo-coupling with sodium thiomethoxide to give 1-(methylthio)-2-(3-nitrophenyl)diazene, then dediazoniated to gain m-nitrothioanisole in high yield. The continuous-flow process minimized accumulation of the energetic intermediate diazonium salt and has a better capacity for adapting large-scale production. A solvent was introduced in the azo-coupling section to create a biphasic flow system. Side products were inhibited eminently in this flow process.

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.

Palladium-Catalyzed Thiomethylation via a Three-Component Cross-Coupling Strategy

In this report, the combination of masked inorganic sulfur and dimethyl carbonate was designed to achieve thiomethylated cross coupling of aryl chlorides. Remarkably, this powerful strategy realized thiomethylation of nucleosides bearing unprotected ribose, chloride-containing pharmaceuticals with late-stage coupling, and herbicides possessing multiple heteroatoms and steric hindrance. Moreover, this protocol is practically amenable to multigram-scale synthesis with a lower catalysis loading and a higher yield.