1137-69-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Chlorophenazine is utilized as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of diverse compounds with potential medicinal applications.
Used in Dye Industry:
In the dye industry, 2-Chlorophenazine serves as a crucial intermediate for the production of various dyes. Its chemical properties enable the creation of vibrant and stable colorants used in textiles, plastics, and other materials.
Used in Disinfectants and Antiseptics:
Leveraging its antibacterial and antifungal properties, 2-Chlorophenazine is employed as an active ingredient in disinfectants and antiseptics. It helps prevent the growth of harmful microorganisms, ensuring cleanliness and reducing the risk of infections.
Used in Cancer Treatment Research:
2-Chlorophenazine has been studied for its potential use in cancer treatment. Its ability to induce apoptosis in cancer cells makes it a promising candidate for further research and development in oncology. However, more studies are needed to fully understand its mechanisms of action and potential side effects.
It is important to handle 2-chlorophenazine with care due to its potential hazards if ingested, inhaled, or absorbed through the skin. Proper safety measures should be taken during its production, use, and disposal to minimize risks to human health and the environment.

InChI:InChI=1/C12H7ClN2/c13-8-5-6-11-12(7-8)15-10-4-2-1-3-9(10)14-11/h1-7H

Upstream product

• 304-81-4 Phenazin-mono-N-Oxyd 
• 1211-09-2 2-chloro-phenazine-5-oxide 
• 7478-17-3 1,1′-(phenazin-5,10-diyl)diethanone 
• 68817-71-0 2-(4-chloroanilino)aniline 
• 16611-15-7 N-(4-chloro-2-nitrophenyl)benzenamine 
• 74002-27-0 N-(3-chlorophenyl)-2-nitroaniline 
• 67-56-1 methanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 88-73-3 2-Chloronitrobenzene 
• 108-42-9 3-chloro-aniline 
• 100-00-5 4-chlorobenzonitrile 
• 62-53-3 aniline 
• 613663-62-0 8-chloro-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine 
• 1621867-49-9 7-chloro-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine 

Downstream Products

• 2876-18-8 2-methoxyphenazine 
• 4190-95-8 2-hydroxyphenazine 
• 303-79-7 2-chlorophenazine 5,10-di-N-oxide 
• 303-80-0 5,10-dioxy-phenazin-2-ol 

Relevant academic research and scientific papers

The silver-mediated annulation of arylcarbamic acids and nitrosoarenes toward phenazines

A silver-mediated annulation between arylcarbamic acids and nitrosoarenes was developed, leading to phenazines in moderate to good yields with complexity and diversity. This procedure proceeded with the sequential ortho[sbnd] C[sbnd]H functionalization of arylcarbamic acids, insertion to nitroso group and decarboxylative annulation.

Preparation method of phenazine compound

To the method, a phenazine compound is prepared through continuous ortho C-H functionalization, nitroso insertion and decarboxylation processes of aryl carbamic acid, wherein a carboxyl amino group serves as a trace-free positioning group.

Rhodium-Catalyzed Reaction of Azobenzenes and Nitrosoarenes toward Phenazines

A rhodium-catalyzed annulative reaction between azobenzenes and nitrosoarenes has been developed, leading to a series of phenazines in moderate to good yields. This procedure proceeds with sequential chelation-assisted addition of aryl C-H to nitrosoarenes and ring closure by electrophilic attack of azo group to aryl. During this transformation, the azo group served as not only a traceless directing group but also a building block in the final products.

Reactivity and substituent effects in the cyclization of N-aryl-2-nitrosoanilines to phenazines

Reactivity of variously substituted N-aryl-2-nitrosoanilines in the reaction of cyclization leading to phenazine derivatives, carried out in the presence of N,O-bis(trimethylsilyl)acetamide (BSA), was estimated on the base of the observed reaction times. A strong opposite effect of substituents located at position para to the nitroso group and those located para to the amino group in the side ring was observed. Mechanistic explanation, based on the electronic properties of the substituents and their mesomeric effects, was presented. The usefulness of the obtained data for the designed syntheses of phenazines was exposed.

Transition-metal-free tandem oxidative removal of benzylic methylene group by C-C and C-N bond cleavage followed by intramolecular new aryl C-N bond formation under radical conditions

A novel tandem oxidative conversion of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines to phenazines has been achieved under transition-metal-free, mild conditions using K2S2O8 or DDQ as the oxidizing agent. The transformation proceeds through oxidative removal of a benzylic methylene group by C-C and C-N bond cleavage followed by a new aryl C-N bond formation under radical conditions.

Regioselective aromatic nucleophilic substitution in N-aryl-2- nitrosoanilines with oxygen and nitrogen nucleophiles

Aromatic nucleophilic substitution of halogens in N-aryl-2-nitrosoanilines with ammonia, alkylamines and alkoxide ions proceeds efficiently and highly regioselectively in the position para to the nitroso group. When two halogen atoms ortho and para are pr

N-Aryl-2-nitrosoanilines as intermediates in the synthesis of substituted phenazines from nitroarenes

N-Aryl-2-nitrosoanilines, available from the reaction of nitroarenes with anilide anions, undergo cycliza-tion to furnish substituted phenazines. The reaction is promoted by potassium carbonate in methanol, N,O-bis(trimethylsilyl) acetamide (BSA) in aprotic solvents, and by acetic acid. The method is illustrated by the synthesis of 1-methoxyphenazine, a precursor of pyocyanine, starting from the appropriate nitro-arene-aniline pairs.

THE REACTION OF QUINOXALINE- AND PHENAZINE-N-OXIDES WITH THIONYL CHLORIDE AND PARATOLUENESULFONYL CHLORIDE

2,3-Diphenylquinoxaline-N-oxide 1 with thionyl chloride gives only 5-chloro- and 6-chloroquinoxaline and very little deoxygenation.Phenazine-N5-oxide 2, in the same conditions, gives mainly 2-chlorophenazine and minor amounts of 1-chlorophenazine, but here deoxygenation is an important pathway.Freshly recrystallized para-toluenesulfonyl chloride gives a high chlorination-to-tosyloxylation ratio.All these results point to a variable ability of acid chlorides to yield homocycle chlorination or acyloxylation; this is confirmed by the observation that phenazine-N5-oxide and phosphoryl chloride give fair amounts of aryl phosphate.