16423-54-4

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-2-(METHYLTHIO)ANILINE is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications. Its unique chemical structure allows it to be a key component in the production of specific therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 5-CHLORO-2-(METHYLTHIO)ANILINE serves as an intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its role in these applications is crucial for enhancing crop protection and improving agricultural productivity.

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 
• 512-56-1 trimethyl phosphite 
• 1004-00-8 4-chloro-2-aminobenzenethiol 
• 20358-00-3 2-amino-5-chlorobenzothiazole 
• 89-61-2 2,5-dichloronitrobenzene 
• 36776-27-9 4-chloro-2-nitro-thiophenol 
• 1006-99-1 2-methyl-5-chloro-benzothiazole 
• 74-88-4 methyl iodide 

Downstream Products

• 19185-66-1 acetic acid-(5-chloro-2-methylsulfanyl-anilide) 
• 57946-15-3 N-(5-Chloro-2-methylsulfanyl-phenyl)-C,C,C-trifluoro-methanesulfonamide 
• 2941-48-2 2,5-Dichloro-benzothiazole 
• 101219-31-2 5-chloro-2-phenylbenzo[b]thiophene 
• 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 

Relevant academic research and scientific papers

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.

Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles

An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides has been successfully developed for the efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. This synthetic protocol, incorporating a halogen atom when forming the five-membered ring of benzothia/selenazoles, is different from the existing ones, where halogenation of the preformed benzothia/selenazole precursors happens. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.

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.

Visible light photocatalytic synthesis of benzothiophenes

The photocatalytic reaction of o-methylthio-arenediazonium salts with alkynes yields substituted benzothiophenes regioselectively through a radical annulation process. Green light irradiation of eosin Y initiates the photoredox catalysis. The scope of the reaction was investigated by using various substituted diazonium salts and different alkynes.

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.

Formation of Sommelet-Hauser-Type Products, 2-Aminoarylmethyl Sulphides, and Nitrenium Ion Products, 2- and 4-Aminoaryl Sulphides, via an N-Arylazasulphonium Salt

Reactions of a salt (1) formed at -60 deg C from trifluoroacetic anhydride and dimethyl sulphoxide (DMSO) with primary and secondary arylamines gave 2-aminoarylmethyl sulphides (6), (6') and (12) by a Sommelet-Hauser rearrangement of an ylide (5) formed by loss of a methyl proton of an N-arylazasulphonium salt (3) in the absence of base.The use of ethyl methyl sulphoxide instead of DMSO afforded a similar product (19b) by loss of not the ethyl but the methyl proton.However, the use of diethyl sulphoxide merely caused loss of an ethyl group from the N-arylazasulphonium salt to yield ethanesulphenanilide (20).The reaction of (1) with N-phenyl-1-naphthylamine gave mainly aminoaryl sulphides (13) and (14) via an arylnitrenium ion from the N-arylazasulphonium salt.In fact, the reaction of dimethyl sulphide (DMS) with arylnitrenium ions formed in the acid decomposition of aryl azides gave no Sommelet-Hauser-type products but 2- and 4-aminoaryl sulphides (22), (22') and (23).We also discuss the possibility of the N-arylazasulphonium salt being formed by reaction of the arylnitrenium ion with DMS.