1783-81-9

Basic information

• Product Name: 3-(METHYLTHIO)ANILINE
• Synonyms: M-(METHYLTHIO)ANILINE;M-THIOANISIDINE;3-AMINOTHIOANISOLE;3-(METHYLMERCAPTO)ANILINE;3-(METHYLTHIO)ANILINE;AKOS 91141;M-AMINOTHIOANISOLE;3-(Methylsulfanyl)aniline
• CAS NO: 1783-81-9
• Molecular Formula: C₇H₉NS
• Molecular Weight: 139.22
• EINECS: 217-232-5
• Product Categories: Amines;Miscellaneous
• Mol File: 1783-81-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 163-165 °C16 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear dark brown liquid
• Density: 1.13 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00182mmHg at 25°C
• Refractive Index: n20/D 1.637(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 3.96±0.10(Predicted)
• BRN: 2078599
• CAS DataBase Reference: 3-(METHYLTHIO)ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(METHYLTHIO)ANILINE(1783-81-9)
• EPA Substance Registry System: 3-(METHYLTHIO)ANILINE(1783-81-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: BY6301000
• F: 2-8-13
• TSCA: T
• HazardClass: IRRITANT, STENCH
• Hazardous Substances Data: 1783-81-9(Hazardous Substances Data)

Usage

Description

3-(METHYLTHIO)ANILINE, also known as 3-(methylthio)aniline, is an organic compound that serves as a crucial intermediate in the pharmaceutical industry. It is characterized by its clear dark brown liquid appearance and is known for its reactivity in various chemical processes.

Uses

Used in Pharmaceutical Industry:
3-(METHYLTHIO)ANILINE is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique chemical properties make it a valuable component in the development of new pharmaceutical compounds.
Used in Chemical Synthesis:
3-(METHYLTHIO)ANILINE is used as a key component in the synthesis of phenyl azobenzene sulfonamide derivatives. These derivatives have potential applications in various fields, including the development of dyes, pigments, and other specialty chemicals.

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits toxic vapors ofNOx and SOx.

Purification Methods

Purify the aniline by fractional distillation in an inert atmostphere. It has UV max at 226 and 300nm. [Bordwell & Cooper J Am Chem Soc 74 10581952.] The N-acetyl derivative has m 78-78.5o (from aqueous EtOH). The hydrochloride has m 260-261o (aqueous EtOH/HCl) or m 225-227o (EtOH/Et2O). [Beilstein 13 H 533, 13 III 1221, 13 IV 1289.]

InChI:InChI=1/C7H9NS/c1-9-7-4-2-3-6(8)5-7/h2-5H,8H2,1H3

Upstream product

• 2524-76-7 1-(methylsulfanyl)-3-nitrobenzene 
• 75-18-3 dimethylsulfide 
• 626-01-7 3-Iodoaniline 
• 1073-29-6 2-(methylsulfenyl)phenol 
• 39082-89-8 3(R,S)-(methylsulphinyl)aniline 
• 4867-37-2 1-chloro-3-methylsulfanylbenzene 
• 33733-73-2 3-bromo-1-(methylthio)benzene 
• 6320-03-2 2-chlorothiphenol 
• 537-91-7 bis(3-nitrophenyl) disulfide 
• 16671-77-5 3-nitrophenyl thiocyanate 
• 16278-29-8 3-nitrobenzenediazonium 
• 19614-16-5 2-bromo-1-(methylsulfanyl)benzene 
• 7664-41-7 ammonia 
• 17733-22-1 2-chlorothioanisole 

Downstream Products

• 106167-23-1 (3-methylsulfanyl-phenyl)-pyridin-2-yl-amine 
• 18902-93-7 N-(3'-methylthiophenyl)anthranylic acid 
• 33733-73-2 3-bromo-1-(methylthio)benzene 
• 65052-48-4 3-cyanophenyl methyl sulfide 
• 107518-44-5 (3-methylsulfanyl-phenyl)-phenyl-diazene 
• 38008-45-6 (3-Methylsulfanyl-phenyl)-carbamic acid 3-methylsulfanylcarbonylamino-phenyl ester 
• 56459-45-1 C₁₄H₂₃N₂O₃PS₂ 
• 3463-03-4 3-methylsulfanylphenol 
• 121417-48-9 N'-(2-chloro-4-pyridinyl-N-oxide)-N-(3-methylthiophenyl)urea 
• 76561-74-5 3,7-bis(methylthio)4-quinolone 
• 66476-41-3 N-(5-Methylsulfanyl-2,4-bis-trifluoromethylsulfanyl-phenyl)-S-trifluoromethyl-thiohydroxylamine 
• 1352310-74-7 3-artesanilide 

Relevant articles and documents

Hydroboration reduction reaction of aromatic nitro compounds without transition metal catalysis

The invention relates to a hydroboration reduction reaction of aromatic nitro compounds without transition metal catalysis. According to the method, triethyl boron and potassium tert-butoxide are used as catalysts for the first time, and an aromatic nitro compound and pinacol borane which is low in price and easy to obtain can be conveniently catalyzed to be subjected to a hydroboration reduction reaction under mild conditions to prepare aromatic amine products. Compared with a traditional method, the method generally has the advantages that the catalyst is cheap and easy to obtain, operation is convenient, and reaction is safe. The selective hydroboration reduction reaction of the non-transition metal reagent catalyzed aromatic nitro compound and pinacol borane is realized for the first time, and a practical new reaction strategy is provided for laboratory preparation or industrial production of aromatic amine products.

N-bromosuccinimide/HCl mediated reduction of sulfoxides to sulfides

An efficient reduction of sulfoxides to sulfides mediated by N-bromosuccinimide (NBS)/HCl system has been developed. This protocol shows good functional group compatibility as well as broad substrates scope with operational simplicity.

Identification of MsrA homologues for the preparation of (R)-sulfoxides at high substrate concentrations

Here we report a methionine sulfoxide reductase A (MsrA) homologue with extremely high substrate tolerance and a wide substrate scope for the biocatalytic preparation of enantiopure sulfoxides. This MsrA homologue which was obtained from Pseudomonas alcaliphila (named paMsrA) showed good activity and enantioselectivity towards a series of aryl methyl/ethyl sulfoxides 1a-1k, with electron-withdrawing or electron-donating substituents at the aromatic ring. Chiral sulfoxides in the R configuration were prepared with approximately 50% of yield and up to 99% enantiomeric excess through the asymmetric reductive resolution of racemic sulfoxide catalyzed by the recombinant paMsrA protein. More importantly, kinetic resolution has been successfully accomplished with high enantioselectivity (E > 200) at initial substrate concentrations up to 320 mM (approximately 45 g L-1), which represents a great improvement in the aspect of the substrate concentration for the biocatalytic preparation of chiral sulfoxides.