16423-54-4

Basic information

• Product Name: 5-CHLORO-2-(METHYLTHIO)ANILINE
• Synonyms: 5-CHLORO-2-(METHYLTHIO)ANILINE;2-Amino-4-Chlorothioanisole
• CAS NO: 16423-54-4
• Molecular Formula: C₇H₈ClNS
• Molecular Weight: 173.66
• Mol File: 16423-54-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 29 °C
• Boiling Point: 92 °C
• Flash Point: 120.7°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 0.00493mmHg at 25°C
• Refractive Index: 1.627
• PKA: 2.52±0.10(Predicted)
• CAS DataBase Reference: 5-CHLORO-2-(METHYLTHIO)ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2-(METHYLTHIO)ANILINE(16423-54-4)
• EPA Substance Registry System: 5-CHLORO-2-(METHYLTHIO)ANILINE(16423-54-4)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39:Wear suitabl
• Hazardous Substances Data: 16423-54-4(Hazardous Substances Data)

Usage

General Description

5-CHLORO-2-(METHYLTHIO)ANILINE is a chemical compound with the molecular formula C7H8ClNS. It is a yellowish solid that is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 5-CHLORO-2-(METHYLTHIO)ANILINE is known to be a derivative of aniline and contains a chlorine atom and a methylthio group. 5-CHLORO-2-(METHYLTHIO)ANILINE may pose health and environmental hazards, and precautions should be taken when handling and disposing of this chemical.

InChI:InChI=1/C7H8ClNS/c1-10-7-3-2-5(8)4-6(7)9/h2-4H,9H2,1H3

Upstream product

• 1889-57-2 (4-chloro-2-nitrophenyl)(methyl)sulfane 
• 75-18-3 dimethylsulfide 
• 3296-06-8 1-azido-3-chlorobenzene 
• 89-61-2 2,5-dichloronitrobenzene 
• 512-56-1 trimethyl phosphite 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 1006-99-1 2-methyl-5-chloro-benzothiazole 
• 74-88-4 methyl iodide 
• 20358-00-3 2-amino-5-chlorobenzothiazole 
• 36776-27-9 4-chloro-2-nitro-thiophenol 

Downstream Products

• 57946-15-3 N-(5-Chloro-2-methylsulfanyl-phenyl)-C,C,C-trifluoro-methanesulfonamide 
• 101219-31-2 5-chloro-2-phenylbenzo[b]thiophene 
• 2941-48-2 2,5-Dichloro-benzothiazole 
• 922511-07-7 (5-chloro-2-(methylthio)phenyl)hydrazine hydrochloride 
• 59083-49-7 (5-Chloro-2-methylsulfanyl-phenyl)-thiourea 
• 59083-48-6 1-Benzoyl-3-(5-chloro-2-methylsulfanyl-phenyl)-thiourea 
• 66624-03-1 5-chloro-2-methylsulfanyl-phenol 
• 19185-66-1 acetic acid-(5-chloro-2-methylsulfanyl-anilide) 

Relevant articles and documents

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization

3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.

2-(Anilinomethyl)imidazolines as α1 adrenergic receptor agonists: The discovery of α10 subtype selective 2′-alkylsulfonyl-substituted analogues

A series of 2′-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of α-adrenergic receptor subtypes α1a, α1b, α1d, α2a, and α2c. Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited α1a subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for α1a vs all other subtypes.