15184-97-1

Usage

Uses

Used in Pharmaceutical Industry:
BenzeneMethanaMine, 3-chloro-N,N-diMethylis utilized as an intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of drugs with specific therapeutic properties.
Used in Pesticide Production:
In the agricultural sector, BenzeneMethanaMine, 3-chloro-N,N-diMethylserves as a crucial ingredient in the manufacturing of certain pesticides. Its incorporation contributes to the effectiveness of these products in controlling and eliminating pests.
Used in Organic Compound Synthesis:
BenzeneMethanaMine, 3-chloro-N,N-diMethylis also employed in the synthesis of other organic compounds for various industrial applications. Its versatility in chemical reactions makes it a valuable building block in organic chemistry.

Upstream product

• 100-97-0 hexamethylenetetramine 
• 766-80-3 1-bromomethyl-3-chlorobenzene 
• 4152-90-3 m-chlorobenzylamine 
• 74-88-4 methyl iodide 
• 108-41-8 1-chloro-3-methylbenzene 
• 124-40-3 dimethyl amine 
• 67-56-1 methanol 
• 766-84-7 3-chloro-benzonitrile 
• 126799-85-7 3-chlorobenzylazide 
• 24167-52-0 N,N-dimethyl-3-chlorobenzamide 
• 50-00-0 formaldehyd 
• 587-04-2 m-Chlorobenzaldehyde 

Downstream Products

• 587-04-2 m-Chlorobenzaldehyde 
• 1192229-92-7 3-chlorobenzyldimethylamine borane 
• 1259324-51-0 N-(tert-butoxycarbonylmethyl)-N-(3-chlorobenzyl)-N,N-dimethylammonium bromide 
• 1384216-50-5 C₁₅H₂₃BClNO₂ 
• 1384216-47-0 1-[5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N,N-dimethylmethanamine 

Relevant academic research and scientific papers

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

Simplified preparation of a graphene-co-shelled Ni/NiO@C nano-catalyst and its application in theN-dimethylation synthesis of amines under mild conditions

The development of Earth-abundant, reusable and non-toxic heterogeneous catalysts to be applied in the pharmaceutical industry for bio-active relevant compound synthesis remains an important goal of general chemical research.N-methylated compounds, as one of the most essential bioactive compounds, have been widely used in the fine and bulk chemical industries for the production of high-value chemicals. Herein, an environmentally friendly and simplified method for the preparation of graphene encapsulated Ni/NiO nanoalloy catalysts (Ni/NiO@C) was developed for the first time, for the highly selective synthesis ofN-methylated compounds using various functional amines and aldehydes under easy to handle, and industrially applicable conditions. A large number of primary and secondary amines (more than 70 examples) could be converted to the correspondingN,N-dimethylamines with the participation of different functional aldehydes, with an average yield of over 95%. A gram-scale synthesis also demonstrated a similar yield when compared with the benchmark test. In addition, it was further proved that the catalyst could easily be recycled because of its intrinsic magnetism and reused up to 10 times without losing its activity and selectivity. Also, for the first time, the tandem synthesis ofN,N-dimethylamine products in a one-pot process, using only a single earth-abundant metal catalyst, whose activity and selectivity were more than 99% and 94%, respectively, for all tested substrates, was developed. Overall, the advantages of this newly developed method include operational simplicity, high stability, easy recyclability, cost-effectiveness of the catalyst, and good functional group compatibility for the synthesis ofN-methylation products as well as the industrially applicable tandem synthesis process.

A Novel Route to Synthesize N,N-Dimethyl Arylmethylamines from Aryl Aldehydes, Hexamethylenetetramine and Hydrogen?

Developing simple and green routes to access valuable chemicals is of significance. Herein, we present a green and novel route to synthesize N,N-dimethyl arylmethylamines (DAMAs) from hexamethylenetetramine (HMTA) and aryl aldehydes in the presence of hydrogen, and a series of DAMAs can be obtained in good yields. This approach opens the precedent for HMTA as N,N-dimethylamine source to synthesize chemicals with N,N-dimethylamine group, which has promising applications for N-containing chemicals synthesis.

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

A Ru(ii) complex mediated synthesis of various N,N-dimethyl and N-monomethyl amines from organic azides using methanol as a methylating agent is reported. This methodology was successfully applied for a one-pot reaction of bromide derivatives and sodium azide in methanol. Notably, by controlling the reaction time several N-monomethylated and N,N-dimethylated amines were synthesized selectively. The practical applicability of this tandem process was revealed by preparative scale reactions with different organic azides and synthesis of an anti-vertigo drug betahistine. Several kinetic experiments and DFT studies were carried out to understand the mechanism of this transformation.

Direct Synthesis of N,N-Dimethylated and β-Methyl N,N-Dimethylated amines from nitriles using methanol: Experimental and computational studies

Direct and selective synthesis of N,N-dimethylated amines from nitriles using methanol as C1 building blocks is reported using an air- and moisture-stable ruthenium complex. Following this process, various aromatic as well as aliphatic nitriles were converted to the corresponding N-methylated amines. Interestingly, tandem C-methylation as well as N-methylation was achieved by introducing multiple methyl groups. The practical aspect of this process was revealed by preparative-scale reactions with different nitriles and the synthesis of anti-allergic drug "avil". Several kinetic experiments and detailed DFT calculations were carried out to understand the mechanism of this process.

Lewis Acid-Catalyzed Reductive Amination of Aldehydes and Ketones with N,N-Dimethylformamide as Dimethylamino Source, Reductant and Solvent

A practical zinc acetate dihydrate-catalyzed reductive amination of various carbonyl compounds with N,N-dimethylformamide (DMF) as dimethylamino (Me2N) source, reductant and solvent has been developed. This reaction shows broad substrate scope,

Efficient and versatile catalytic systems for the n-methylation of primary amines with methanol catalyzed by n-heterocyclic carbene complexes of iridium

Efficient and versatile catalytic systems were developed for the N-methylation of both aliphatic and aromatic primary amines using methanol as the methylating agent. Iridium complexes bearing an Nheterocyclic carbene (NHC) ligand exhibited high catalytic performance for this type of transformation. For aliphatic amines, selective N,N-dimethylation was achieved at low temperatures (50-90 °C). For aromatic amines, selective N-monomethylation and selective N,N-dimethylation were accomplished by simply changing the reaction conditions (presence or absence of a base with an appropriate catalyst). These findings can be used to develop methods for synthesizing useful amine compounds having N-methyl or N,N-dimethyl moieties.

Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis

Herein we report a highly meta-selective C-H arylation using simple tertiary amines as the directing group. This method takes advantage of Pd/norbornene catalysis, offering a distinct strategy to control the site selectivity. The reaction was promoted by commercially available AsPh3 as the ligand and a unique "acetate cocktail". Aryl iodides with an ortho electron-withdrawing group were employed as the coupling partner. A wide range of functional groups, including some heteroarenes, are tolerated under the reaction conditions. In addition, the amine directing group can be easily installed and transformed to other common versatile functional groups. We expect this C-H functionalization mode to have broad implications for developing other meta-selective transformations beyond this work.

INDOLIZINE DERIVATIVES AS PHOSHOINOSITIDE 3-KINASES INHIBITORS

Compounds of formula (I), defined herein, inhibit phosphoinositide 3-kinases (PI3K) and are useful for the treatment of disorders associated with PI3K enzymes.

Iridium-catalyzed, substrate-directed C-H borylation reactions of benzylic amines

The iridium-catalyzed arene C-H borylation reaction of benzylic amines has been developed, which inverts the typical steric-controlled product distribution to provide ortho-substituted boronate esters. Picolylamine was found to be an ideal ligand to replace 4,4′-di-tert-butylbipyridine to induce the directing effect. Preliminary experiments are consistent with a mechanism involving dissociation of one amine of the hemilabile diamine ligand.