38939-88-7

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-4-nitrotoluene is used as a synthetic intermediate for the development of quinoxaline derivatives. These derivatives are significant in the creation of a positron emission tomography (PET) radiotracer. The radiotracer is specifically designed for the imaging of N-Methyl-D-aspartate receptor (NMDAR), which plays a crucial role in various neurological functions and disorders.
The application of 3-Chloro-4-nitrotoluene in the pharmaceutical industry is primarily due to its ability to contribute to the synthesis of compounds that can be used in advanced medical imaging techniques. This allows for better understanding, diagnosis, and treatment of conditions related to the NMDAR, such as neurodegenerative diseases and psychiatric disorders.

InChI:InChI=1/C7H6ClNO2/c1-5-2-3-7(9(10)11)6(8)4-5/h2-4H,1H3

Upstream product

• 108-41-8 1-chloro-3-methylbenzene 
• 578-46-1 5-methyl-2-nitroaniline 
• 34648-99-2 4-chloro-2-methyl-5-nitroaniline 
• 7697-37-2 nitric acid 
• 540-23-8 p-toluidine hydrochloride 
• 2028-72-0 m-toluenediazonium chloride 
• 3113-72-2 5-methyl-2-nitrobenzoic acid 
• 610-39-9 3,4-Dinitrotoluene 
• 615-65-6 2-chloro-4-methyl-benzenamine 

Downstream Products

• 104740-93-4 3-(N-piperidino)-4-nitrotoluene 
• 108620-61-7 2-(5-methyl-2-nitro-phenylsulfanyl)-benzoic acid methyl ester 
• 39608-47-4 3-chloro-4-nitrobenzoic acid 
• 27332-17-8 4-methyl-2-(2-nitro-phenylsulfanyl)-aniline 
• 615-65-6 2-chloro-4-methyl-benzenamine 
• 21261-92-7 6-Methyl-3-butyl-benzothiazolin-2-thion 
• 21261-95-0 6-methyl-3-(4-methyl-benzyl)-3H-benzothiazole-2-thione 
• 21261-94-9 6-methyl-3-(2-methyl-benzyl)-3H-benzothiazole-2-thione 
• 52062-85-8 (5,5'-dimethyl-2,2'-dinitrophenyl)disulfide 
• 77455-53-9 Acetic acid acetoxy-(3-chloro-4-nitro-phenyl)-methyl ester 
• 146139-68-6 C₁₃H₉F₂NO₃ 
• 64113-86-6 2-nitro-5-methylbenzonitrile 
• 74683-22-0 3'-hydroxy-5-methyl-2-nitrodiphenyl ether 
• 30321-98-3 (5-Methyl-2-nitrophenylthio)essigsaeure 

Relevant academic research and scientific papers

The polyhedral nature of selenium-catalysed reactions: Se(iv) species instead of Se(vi) species make the difference in the on water selenium-mediated oxidation of arylamines

Selenium-catalysed oxidations are highly sought after in organic synthesis and biology. Herein, we report our studies on the on water selenium mediated oxidation of anilines. In the presence of diphenyl diselenide or benzeneseleninic acid, anilines react with hydrogen peroxide, providing direct and selective access to nitroarenes. On the other hand, the use of selenium dioxide or sodium selenite leads to azoxyarenes. Careful mechanistic analysis and 77Se NMR studies revealed that only Se(iv) species, such as benzeneperoxyseleninic acid, are the active oxidants involved in the catalytic cycle operating in water and leading to nitroarenes. While other selenium-catalysed oxidations occurring in organic solvents have been recently demonstrated to proceed through Se(vi) key intermediates, the on water oxidation of anilines to nitroarenes does not. These findings shed new light on the multifaceted nature of organoselenium-catalysed transformations and open new directions to exploit selenium-based catalysis.

Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides

A useful and efficient approach for the synthesis of nitroarenes from several aromatic amines (including heterocycles) using peroxide and base has been developed. This oxidative reaction is very easy to handle and afforded the products in good yields. Formation of benzamides from benzylamine was also successfully carried out with this metal-free catalytic system in good to excellent yields.

Synthetic method of aryl halide taking aryl carboxylic acid as raw material

A synthetic method of an aryl halide taking aryl carboxylic acid as a raw material is characterized in that a corresponding aryl halide is formed by carrying out substitution reaction on an aryl carboxylic acid compound and haloid salt MX in an organic solvent under the condition that oxygen, a silver catalyst, a copper additive and a bidentate nitrogen ligand exist, wherein M in MX represents alkali metal or alkaline earth metal, and X represents F, Cl, Br or I. Compared with a conventional aryl halide synthetic method, the synthetic method disclosed by the invention has the obvious advantages that reaction raw materials (comprising aryl carboxylic acid and MX) are cheap and easy to obtain, the using amount of a metal catalyst is small, pollution to the environment when the oxygen is used as an oxidant is the smallest, good tolerance to various functional groups on an aromatic ring is obtained, the yield is high, and the like. The synthetic method disclosed by the invention can be widely applied to synthesis in the fields of medicine, materials, natural products and the like in industry and academia.

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.

PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS

Compounds of the formula I or II: wherein X, m, Ar, R1 and R2 are as defined herein. The subject compounds are useful for treatment of IRAK-mediated conditions.

Reaction of dimethyldioxirane with aniline hydrohalides

Oxidation of aromatic amine hydrohalides (aniline hydrochloride, hydrobromide, and hydrofluoride; 4-methylaniline hydrochloride and hydrobromide; 3-methylaniline and N,N-diethylaniline hydrochlorides) with dimethyldioxirane was studied. The product composition was analyzed in relation to the reactant ratio.

Studies on antiinflammatory agents. I. Synthesis and pharmacological properties of 2'-phenoxymethanesulfonanilide derivatives

Various 2'-phenoxymethanesulfonanilide derivatives were synthesized and evaluated for antiinfiammatory and analgesic activities. Some compounds bearing an electron-attracting substituent at the 4'-position strongly inhibited adjuvant-induced arthritis in rats and acetic acid-induced writhing syndrome in mice without causing gastro-intestinal irritation. Among them, 4'-cyano-(FK867) and 4'-acetyl-(FK3311) 2'-(2,4-difluorophenoxy)methanesulfonanilides were selected as the candidates for further development.