769-06-2

Basic information

• Product Name: 2,6,N,N-Tetramethylaniline
• Synonyms: 2,6,N,N-Tetramethylaniline;N,N,2,6-Tetramethylbenzenamine
• CAS NO: 769-06-2
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• Mol File: 769-06-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: -36°C
• Boiling Point: 220.76°C (estimate)
• Flash Point: 78.9°C
• Appearance: /
• Density: 0.9147
• Vapor Pressure: 0.338mmHg at 25°C
• Refractive Index: 1.5157 (estimate)
• PKA: 6.18±0.36(Predicted)
• CAS DataBase Reference: 2,6,N,N-Tetramethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6,N,N-Tetramethylaniline(769-06-2)
• EPA Substance Registry System: 2,6,N,N-Tetramethylaniline(769-06-2)

Safety Data

• Hazardous Substances Data: 769-06-2(Hazardous Substances Data)

Usage

General Description

2,6,N,N-Tetramethylaniline, also known as N,N,N',N'-tetramethyl-p-phenylenediamine, is an organic compound with the chemical formula C10H15N. It is a derivative of aniline and is commonly used as a reagent in organic synthesis and as a precursor to dyes and polymers. 2,6,N,N-Tetramethylaniline is a colorless to pale yellow liquid with a strong amine odor, and it is insoluble in water but soluble in organic solvents. It is considered to be a moderately toxic compound, causing irritation to the skin, eyes, and respiratory system upon exposure. This chemical is primarily used in the production of azo dyes, as well as in the synthesis of antioxidants and stabilizers for polymers.

InChI:InChI=1/C10H15N/c1-8-6-5-7-9(2)10(8)11(3)4/h5-7H,1-4H3

Upstream product

• 50-00-0 formaldehyd 
• 767-71-5 N-methyl-2,6-dimethylaniline 
• 98-04-4 phenyltrimethylammonium iodide 
• 77-78-1 dimethyl sulfate 
• 87-62-7 2,6-dimethylaniline 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 85802-75-1 4-dimethylamino-3,5-dimethylaniline 
• 35203-02-2 2,6-dimethyl-N-methylene benzamine 
• 616-38-6 carbonic acid dimethyl ester 
• 160852-85-7 2-[2-(2-methoxyethoxy)ethoxy]ethyl methyl carbonate 
• 24558-36-9 N,N,2,6-Tetramethyl-4-nitroaniline 
• 1247014-56-7 C₁₀H₁₅NO 
• 124-38-9 carbon dioxide 

Downstream Products

• 57678-72-5 2-Chloro-N-(3-dimethylamino-2,4-dimethyl-benzyl)-acetamide 
• 57678-74-7 2-Chloro-N-{5-[(2-chloro-acetylamino)-methyl]-3-dimethylamino-2,4-dimethyl-benzyl}-acetamide 
• 76166-10-4 3,5-dimethyl-4-(dimethylamino)benzaldehyde 
• 85802-74-0 N,2,6-trimethyl-4-nitroaniline 
• 75560-69-9 3,4-dichloro-N,N,2,6-tetramethylaniline 
• 75560-68-8 3,5-chloro-N,N,2,6-tetramethylaniline 
• 75560-66-6 3-chloro-N,N,2,6-tetramethylaniline 
• 767-71-5 N-methyl-2,6-dimethylaniline 
• 88842-23-3 [2,6-Dimethyl-4-(3-methyl-3H-naphtho[1,2-d]imidazol-2-yl)-phenyl]-dimethyl-amine 
• 18835-47-7 N-(2,6-dimethylphenyl)-N-methylacetamide 

Relevant articles and documents

B(C6F5)3-Catalyzed C-H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant

An efficient method for the coupling of N-alkylamines with silicon enolates to generate β-amino carbonyl compounds is disclosed. These reactions proceed by activation of α-amino C-H bonds by B(C6F5)3, which likely generate

Diverse catalytic reactivity of a dearomatized PN3P?-nickel hydride pincer complex towards CO2 reduction

A dearomatized PN3P?-nickel hydride complex has been prepared using an oxidative addition process. The first nickel-catalyzed hydrosilylation of CO2 to methanol has been achieved, with unprecedented turnover numbers. Selective methylation and formylation of amines with CO2 were demonstrated by such a PN3P?-nickel hydride complex, highlighting its versatile functions in CO2 reduction.

Selective formylation and methylation of amines using carbon dioxide and hydrosilane catalyzed by alkali-Metal carbonates

The formylation and methylation of amines with carbon dioxide and hydrosilanes are emerging yet important types of transformations for CO2. Catalytic methods effective for both reactions with wide substrate scopes are rare because of the difficulty in controlling the selectivity. Herein, we report that simple and readily available inorganic bases alkali-metal carbonates, especially cesium carbonatecatalyze both the formylation and methylation reactions efficiently under mild conditions. The selectivity can be conveniently controlled by varying the reaction temperature and silane. A “cesium effect” on both reactions was observed by comparing the catalytic activity of various alkali-metal carbonates. Combined experimental and computational studies suggested the following reaction mechanism: (i) activation of Si?H by Cs2CO3, (ii) insertion of CO2 into Si?H, (iii) formylation of amines by silyl formate, and (iv) reduction of formamides to methylamines.