132540-71-7

Basic information

• Product Name: 1,4-Benzenediamine, N,N-dimethyl-N'-(4-methylphenyl)-
• CAS NO: 132540-71-7
• Molecular Formula: C15H18N2
• Molecular Weight: 226.321
• Mol File: 132540-71-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,4-Benzenediamine, N,N-dimethyl-N'-(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Benzenediamine, N,N-dimethyl-N'-(4-methylphenyl)-(132540-71-7)
• EPA Substance Registry System: 1,4-Benzenediamine, N,N-dimethyl-N'-(4-methylphenyl)-(132540-71-7)

Safety Data

• Hazardous Substances Data: 132540-71-7(Hazardous Substances Data)

Usage

Chemical structure

Diamine derivative of benzene with two amino groups on opposite ends of a phenyl ring

Usage

Production of hair dyes and other cosmetic products

Hair color properties

Produces dark, permanent hair colors

Commonly used in

Many hair dye formulations

Health concerns

Linked to skin irritation and allergic reactions

Regulatory status

Restricted or banned in some countries for use in cosmetics

Precaution

Caution should be exercised when using products containing this chemical

Upstream product

• 67-56-1 methanol 
• 132540-70-6 C₁₂H₁₇NO₂ 
• 121-69-7 N,N-dimethyl-aniline 
• 109-72-8 n-butyllithium 
• 99-99-0 1-methyl-4-nitrobenzene 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 106-49-0 p-toluidine 
• 7353-91-5 4-dimethylaminophenylmagnesium bromide 

Relevant articles and documents

Preparation of diarylamines by the addition of 4-(N,N-dimethylamino)phenyllithium to nitroarenes

The addition of 4-(N,N-dimethylamino)phenyllithium to nitroarenes in THF (-78°C) affords the corresponding diarylamines in one-pot and the reaction appears to be general in scope. A 'nitroso'-based mechanism is proposed for this novel nitroreductive N-arylation reaction.

Evidence for "cocktail"-type catalysis in Buchwald-Hartwig reaction. A mechanistic study

The mechanism of the C-N cross-coupling reaction, catalyzed by palladium complexes with N-heterocyclic carbene ligands (Pd/NHC), was evaluated in detail at the molecular and nanoscale levels. For the first time, the formation of a "cocktail"-type catalytic system was proven for the Buchwald-Hartwig reaction. The unique ability of the Pd/NHC system to generate several types of catalytic centers (Pd complexes, clusters and nanoparticles) and the involvement of complementary pathways (homogeneous and heterogeneous) were discovered to take place in a "one pot"manner directly in the reaction vessel. Access to various catalytic centers from a single and readily available Pd/NHC complex is the key to designing a universal catalytic system with adaptive tuning capability. This journal is

Mechanism of the Reaction of Carbon and Nitrogen Nucleophiles with the Model Carcinogens O-Pivaloyl-TV-arylhydroxylamines: Competing SN2 Substitution and SN1 Solvolysis

The reaction of N,N-dimethylaniline (4) and aniline (5) with the O-pivaloyl-N-arylhydroxylamines 1a-f) in MeOH exhibits second-order kinetics and generates products of nucleophilic attack on the nitrogen of the hydroxylamine derivative. The characteristics of this reaction are not consistent with a nitrene or SET mechanism, an SN1 reaction with rate-limiting attack of the nucleophile, or nucleophile-assisted ionization. The only mechanism consistent with the available data, including substituent effects (ρ+ ≈ -3.0), cyclic voltammetry results, and product identifications, is an SN2 process. This reaction occurs in competition with an SN1 solvolysis that shows significant substituent dependence (ρ+ = -8.5). The reaction of 1 with 5 generates products of nucleophilic attack by both carbon (8, 9) and nitrogen (10). Competitive attack by carbon apparently occurs because of transition-state stabilization caused by the incipient C-N bond. The successful competition of the 8N2 reactions with SN1 solvolysis for the esters 1a and 1b, which are similar in reactivity to the putative carcinogens 2a-c, indicates that certain adducts isolated from in vivo experiments, including 3, may be formed via SN2 mechanisms.