92-39-7

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Chlorophenothiazine is used as a starting reagent for the synthesis of N-(10H-phenothiazin-1-yl) benzene sulphonamide, a compound with potential pharmaceutical applications.
Used in Research and Development:
As a metabolite of Chlorpromazine, 2-Chlorophenothiazine is utilized in research and development for understanding the properties and behavior of phenothiazine derivatives, which can contribute to the advancement of pharmaceutical and chemical sciences.

InChI:InChI=1/C12H8ClNS/c13-8-5-6-12-10(7-8)14-9-3-1-2-4-11(9)15-12/h1-7,14H

Upstream product

• 101-17-7 3-chlorodiphenylamine 
• 105790-02-1 2-(2-bromo-phenylsulfanyl)-5-chloro-aniline 
• 100622-35-3 acetic acid-[2-(2-bromo-phenylsulfanyl)-5-chloro-anilide] 
• 104115-87-9 5-chloro-2-(4-chloro-2-nitro-phenylsulfanyl)-aniline 
• 142-04-1 aniline hydrochloride 
• 107522-19-0 N-[2-(5-chloro-2-nitrophenylthio)phenyl]acetamide 
• 4548-56-5 4-chloro-2-nitrophenyl phenyl sulfide 
• 92-84-2 10H-phenothiazine 
• 92044-64-9 2-Chloro-phenothiazine-10-carboxylic acid hydrazide 
• 100234-25-1 2-chloro-N-trifluoroacetylphenothiazine 
• 96124-86-6 2,2,2-trifluoro-1-(10H-phenothiazin-10-yl)ethan-1-one 
• 5182-81-0 2-chloro-10-vinylphenothiazine 
• 49864-70-2 DL-10-<β-N-(1,4-Diazabicyclo<4.3.0>nonanyl)propionyl>-2-chlorophenothiazine 
• 69-09-0 chlorpromazine hydrochloride 

Downstream Products

• 3810-87-5 2-chloro-10-(3-pyrrolidin-1-yl-propyl)-10H-phenothiazine 
• 36798-98-8 2-chloro-phenothiazine-10-carbonyl chloride 
• 2765-59-5 2-chloro-10-(3-chloropropyl)-10H-phenothiazine 
• 2095-24-1 chlorfenethazine 
• 1225-64-5 Norchlorpromazine 
• 17210-75-2 2-chloro-10-(2'-chloroethyl)-10H-phenothiazine 
• 604-73-9 Chlorpromazin 
• 50-53-3 2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine 
• 4414-83-9 3-(2-chloro-10H-phenothiazin-10-yl)propanonitrile 
• 84-01-5 chlorproethazine 
• 16189-69-8 2-chloro-1-(2-chloro-10H-phenothiazin-10-yl)ethan-1-one 
• 1032-19-5 2-chloro-10-(β-chloropropionyl)phenothiazine 
• 1927-43-1 2-chloro-10H-phenothiazine 5-oxide 
• 101976-38-9 2-Chlor-10--phenothiazin 

Relevant academic research and scientific papers

Antioxidant and method for preparing antioxidant

The invention discloses an antioxidant and a method for preparing the antioxidant. An intermediate 2 reacts with an intermediate 5 to obtain an intermediate 14, the intermediate 14 isoxidized with potassium permanganate, an esterification reaction is then carried out with an intermediate 13 to obtain an intermediate 15, the intermediate 15 is reduced with tin powder to obtain an intermediate 16, the intermediate 16 and the intermediate 8 are subjected to dehydration condensation, the antioxidant is prepared, the antioxidant contains a large number of sulfur atoms, the sulfur atoms can be oxidized to form sulfoxide and sulfone compounds, the antioxidant has good oxidation resistance, free radicals generated by macromolecules can be captured, then the free radical branching reaction is inhibited, and the antioxidant activity is improved. The oxidation resistance of the high-molecular material is improved, and the self relative molecular mass is large and is not easy to separate out from the high-molecular material.

One-Pot Tandem Access to Phenothiazine Derivatives from Acetanilide and 2-Bromothiophenol via Rhodium-Catalyzed C-H Thiolation and Copper-Catalyzed C-N Amination

A one-pot and step economic reaction involving Rh(III)-catalyzed C-H thiolation and relay Cu(II)-catalyzed C-N amination of acetanilide and 2-bromothiophenol is reported here, with several valuable phenothiazine products obtained. This synthesis protocol proceeds from easily starting materials, demonstrating high atom economy, broad substrate scope, and good yield. Furthermore, the directing group can be easily eliminated, and chlorpromazine is provided in a large scale; thus this synthesis protocol could be utilized to construct phenothiazine scaffolds.

Efficient and regioselective synthesis of phenothiazine via ferric citrate catalyzed C-S/C-N cross-coupling

Efficient C-S and C-N cross-coupling reactions have been developed for regioselective, scalable and environmentally benign synthesis of substituted phenothiazine derivatives. Cross-coupling reactions were demonstrated on various challenging substrates using non-toxic, highly economical, readily available ferric citrate as a catalyst to get desired product with high regioselectivity. Atom economy is the added advantage of this protocol since additional N-protection step before coupling and eventual deprotection of the same to obtain the desired product arenot required. To the best of our knowledge, this is the first report on the use of inexpensive ferric citrate as a catalyst without involving any ligand for the synthesis of regioselectively substituted phenothiazine.

Iron catalytic phenothiazine synthetic method of compound

The invention provides a synthetic method of an iron-catalyzed phenothiazine compound. The synthetic method comprises the following step: in the presence of an iron salt catalyst, a ligand and an alkali, carrying out C-S coupling, C-N coupling and deacylation reaction on raw materials (N-(2-sulfydryl phenyl) acetamide and o-dibromobenzene) at a certain temperature to obtain the phenothiazine compound. The synthetic method provided by the invention is simple in operation, mild in condition, wide in application range, relatively high in yield and short in reaction time and has a good industrial prospect.

Transition-metal-free synthesis of phenothiazines from S-2-acetamidophenyl ethanethioate and ortho-dihaloarenes

An efficient cesium carbonate-mediated synthesis of phenothiazine derivatives from S-2-acetamidophenyl ethanethioates and ortho-dihaloarenes has been developed. This protocol affords an efficient approach for the construction of phenothiazine derivatives without the need of transition-metal catalyst or ligand. A plausible mechanism is proposed.

Radical Route to 1,4-Benzothiazine Derivatives from 2-Aminobenzenethiols and Ketones under Transition-Metal-Free Conditions

Transition-metal-free radical access to 1,4-benzothiazine derivatives from o-aminobenzenethiols is disclosed. This procedure is available for various ketones including α,β-unsaturated, cyclic, linear, and fluoroalkyl ketones to generate a number of 1,4-benzothiazines, which exist in numerous bioactive and natural molecules, rendering this protocol attractive to both synthetic and medicinal chemistry.

A method of synthesizing phenoxthine compounds

The invention develops a method for synthesizing phenothiazine compounds by using benzothiazole and derivatives thereof as well as 1-bromo-2-iodobenzene and derivatives thereof as raw materials and copper or copper salt/N-alkoxy-1H-pyrrolic amide system as a copper catalyst. The method is a brand-new method for synthesizing phenothiazine compounds. The method has the characteristics of low temperature, short reaction time, low solvent toxicity and wide substrate adaptability, and has wide application prospects in the aspect of preparation of medicines, pesticides and materials.

Copper-Catalyzed Domino Reactions for the Synthesis of Phenothiazines

A method for the one-pot synthesis of phenothiazines from benzothiazoles and aryl ortho-dihalides was explored. Preliminary work on the mechanism of the reaction suggested that it follows a domino process, including the hydrolysis of benzothiazoles followed by C-S coupling and C-N coupling. The low loading of the catalyst system (5 mol-% for both copper and ligand), the mild experimental conditions (90 °C, 12 h), and the use of a green reaction medium make this synthesis very attractive to academia and industry. A copper-catalyzed domino reaction consisting of the hydrolysis of benzothiazoles followed by C-S and C-N couplings for the synthesis of phenothiazines from benzothiazoles and aryl ortho-dihalides is described. The low loading of the catalyst system, mild experimental conditions, and the use of polyethylene glycol as the solvent make this synthetic approach very attractive to academia and industry.

Method for the Synthesis of Phenothiazines via a Domino Iron-Catalyzed C-S/C-N Cross-Coupling Reaction

An environmentally benign and efficient method has been developed for the synthesis of phenothiazines via a tandem iron-catalyzed C-S/C-N cross-coupling reaction. Some of the issues typically encountered during the synthesis of phenothiazines in the presence of palladium and copper catalysts, including poor substrate scope, long reaction times and poor regioselectivity, have been addressed using this newly developed iron-catalyzed method.

A facile synthesis of pechmann dyes

A facile synthesis of Pechmann dyes has been accomplished by the reaction of substituted N-phenacyl-4-dimethylaminopyridinium halides with dimethyl maleate in the presence of DBU. Based on a related 4-DMAP elimination product and an isolated monolactone intermediate a reaction mechanism has been proposed. The scope of this synthetic method is determined by the availability of α-haloaroyl or heteroaroyl derivatives. DBU=1,8-diazabicycloundec-7-ene, DMAP=4-dimethylaminopyridine. A facile synthesis of Pechmann dyes has been accomplished by the reaction of substituted N-phenacyl-4-dimethylaminopyridinium halides with dimethyl maleate in the presence of DBU (see scheme). Based on a related 4-DMAP elimination product and an isolated monolactone intermediate a reaction mechanism has been proposed. The scope of this synthetic method is determined by the availability of α-haloaroyl or heteroaroyl derivatives. DBU=1,8-diazabicycloundec-7-ene, DMAP=4-dimethylaminopyridine.