15184-97-1

Basic information

• Product Name: BenzeneMethanaMine, 3-chloro-N,N-diMethyl-
• Synonyms: BenzeneMethanaMine, 3-chloro-N,N-diMethyl-;3-Chloro-N,N-dimethyl-benzenemethanamine
• CAS NO: 15184-97-1
• Molecular Formula: C₉H₁₂ClN
• Molecular Weight: 169.65128
• Mol File: 15184-97-1.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BenzeneMethanaMine, 3-chloro-N,N-diMethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: BenzeneMethanaMine, 3-chloro-N,N-diMethyl-(15184-97-1)
• EPA Substance Registry System: BenzeneMethanaMine, 3-chloro-N,N-diMethyl-(15184-97-1)

Safety Data

• Hazardous Substances Data: 15184-97-1(Hazardous Substances Data)

Usage

General Description

BenzeneMethanaMine, 3-chloro-N,N-diMethyl- is a chemical compound with the molecular formula C8H10ClN. It is also known by the name 3-Chloro-N,N-dimethylbenzylamine and is used in a variety of industrial applications, such as in the production of pharmaceuticals, pesticides, and other organic compounds. BenzeneMethanaMine, 3-chloro-N,N-diMethyl- is a colorless liquid with a strong, ammonia-like odor, and it is considered to be a hazardous substance due to its toxic and irritant properties. It is important to handle and store this chemical with caution and in accordance with safety regulations.

Upstream product

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

Downstream Products

• 1192229-92-7 3-chlorobenzyldimethylamine borane 
• 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 
• 1259324-51-0 N-(tert-butoxycarbonylmethyl)-N-(3-chlorobenzyl)-N,N-dimethylammonium bromide 
• 587-04-2 m-Chlorobenzaldehyde 

Relevant articles and documents

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.

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.