294190-16-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-iodo-6-nitrotoluene is used as a key intermediate in the synthesis of new drugs for various therapeutic applications. Its unique molecular structure allows for the development of innovative pharmaceutical compounds with improved efficacy and safety profiles.
Used in Agrochemical Industry:
In the agrochemical industry, 4-chloro-2-iodo-6-nitrotoluene is used as a precursor in the production of pesticides and herbicides. Its chemical properties enable the creation of effective and targeted agrochemicals that can protect crops from pests and diseases while minimizing environmental impact.
Used in Dye Industry:
4-Chloro-2-iodo-6-nitrotoluene is utilized in the dye industry for the production of various dyes with specific color properties and stability. Its molecular structure allows for the development of dyes with improved performance characteristics, such as enhanced colorfastness and resistance to fading.
Overall, 4-chloro-2-iodo-6-nitrotoluene is a valuable chemical compound with diverse applications across different industries, including pharmaceuticals, agrochemicals, and dyes. Its unique properties and potential for use in organic synthesis make it an essential component in the development of innovative products and solutions.

Upstream product

• 89-59-8 4-chloro-2-nitrotoluene 
• 219312-44-4 5-chloro-2-methyl-3-nitro-aniline 
• 35572-79-3 5-chloro-2-methyl-1,3-dinitro-benzene 
• 606-20-2 2,6-dinitrotoluene 

Downstream Products

• 870606-29-4 5-chloro-3-iodo-2-methylaniline 
• 871339-21-8 1-(5-chloro-3-iodo-2-methylphenyl)piperazine 
• 871464-75-4 2-[(5-chloro-2-methyl-3-piperazin-1-ylphenyl)oxy]-N,N-dimethylethanamine 
• 871339-24-1 3-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-N,N-dimethylprop-2-yn-1-amine 
• 871464-70-9 N'-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-N,N-dimethylethane-1,2-diamine 
• 871339-22-9 1,1-dimethylethyl 4-(5-chloro-3-iodo-2-methylphenyl)piperazine-1-carboxylate 
• 871339-40-1 1,1-dimethylethyl 4-(5-chloro-3-hydroxy-2-methylphenyl)piperazine-1-carboxylate 
• 871464-73-2 3-(5-chloro-2-methyl-3-piperazin-1-ylphenyl)-N,N-diethylpropan-1-amine 
• 871339-34-3 1,1-dimethylethyl 4-[5-chloro-2-methyl-3-(3-oxopropyl)phenyl]piperazine-1-carboxylate 
• 871339-41-2 1,1-dimethylethyl 4-(5-chloro-3-{[2-(dimethylamino)ethyl]oxy}-2-methylphenyl)piperazine-1-carboxylate 
• 871339-23-0 1,1-dimethylethyl 4-{5-chloro-3-[3-(dimethylamino)prop-1-yn-1-yl]-2-methylphenyl}piperazine-1-carboxylate 
• 871339-25-2 1,1-dimethylethyl 4-(5-chloro-3-([2-(dimethylamino)ethyl]amino)-2-methylphenyl)-piperazine-1-carboxylate 
• 871339-39-8 1,1-dimethylethyl 4-[5-chloro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate 
• 871339-35-4 1,1-dimethylethyl 4-{5-chloro-3-[3-(diethylamino)propyl]-2-methylphenyl}piperazine-1-carboxylate 

Relevant academic research and scientific papers

Application of C-H Functionalization in the Development of a Concise and Convergent Route to the Phosphatidylinositol-3-kinase Delta Inhibitor Nemiralisib

This paper describes the development of an improved and scalable method for the manufacture of nemiralisib, a phosphatidylinositol-3-kinase delta inhibitor. Incorporation of three consecutive catalytic reactions, including a palladium-catalyzed C-H functionalization and an iridium-catalyzed borylation, significantly simplified and shortened the synthetic sequence. The revised route was successfully implemented in a pilot plant on a multikilogram scale to deliver >100 kg of product.

Synthesis of tricyclic indole-2-caboxylic acids as potent NMDA-glycine antagonists

The practical synthesis of a series of tricyclic indole-2-carboxylic acids, 7-chloro-3-arylaminocarbonylmethyl-1,3,4,5-tetrahydrobenz [cd]indole-2-carboxylic acids, as a new class of potent NMDA-glycine antagonists is described. The synthetic route to the key intermediate 12a comprises a regioselective iodination of 4-chloro-2-nitrotoluene, modified Reissert indole synthesis, Jeffery's Heck-type reaction with allyl alcohol, Wittig-Horner-Emmons reaction, and iodination at the indole C-3 position. The key step in the route is an intramolecular cyclization of 12a to give the tricyclic indole structure. Two methods of cyclization, (1) an intramolecular radical cyclization of 12a and (2) a sequence of intramolecular Heck reaction of 12a followed by a 1,4-reduction, were performed. The resulting tricyclic indole diester 13a was selectively hydrolyzed to afford the desired tricyclic indole monocarboxylic acid 16 on a multihundred gram scale without any chromatographic purifications. Optical resolution of 16 to (-)-isomer 17 and (+)-isomer 18 was carried out, and the resulting isomers were derivatized, respectively. Evaluation of the optically active derivatives for affinity to the NMDA-glycine binding site using the radio ligand binding assay with [3H]-5,7-dichlorokynurenic acid revealed that the derivatives of (-)-isomer 17 were more potent than the others and that especially substituted anilide (-)-isomer 24 (Ki = 0.8 nM) showed high affinity.