2836-03-5

Usage

Uses

Used in Hair Coloring Industry:
N,N-DIMETHYL-PHENYLENEDIAMINE is used as a dye precursor for hair dyes and hair coloring products. It is essential for the permanent coloration of hair, as it reacts with hydrogen peroxide to produce the final oxidative dye molecule.
Used in Cosmetic Products:
N,N-DIMETHYL-PHENYLENEDIAMINE is used as a component in cosmetic products, specifically in hair dyes and hair coloring products, to achieve the desired coloration effect. However, due to its potential allergenic and irritant properties, there are regulations in place to limit its use and concentration in these products to ensure consumer safety and minimize environmental impact.

InChI:InChI=1/C8H12N2/c1-10(2)8-6-4-3-5-7(8)9/h3-6H,9H2,1-2H3

Upstream product

• 874-52-2 N,N-dimethylaniline N-oxide 
• 698-00-0 2-bromo-N,N-dimethylaniline 
• 1493-27-2 ortho-nitrofluorobenzene 
• 89291-23-6 2-(N,N-dimethylamino)phenylboronic acid 
• 95-54-5 1,2-diamino-benzene 
• 77-78-1 dimethyl sulfate 
• 88-74-4 2-nitro-aniline 
• 696604-98-5 N-(2-N,N-dimethylaminophenyl)-1,1-dimethylethyl ester carbamic acid 
• 687603-39-0 N-(o-Dimethylamino-phenyl)-carbamoyl-cyanid 
• 610-17-3 N,N-dimethyl-2-nitro-benzenamine 

Downstream Products

• 26639-38-3 1-hydroxy-[2]naphthoic acid-(2-dimethylamino-anilide) 
• 3743-22-4 2-hydroxy-N,N-dimethylaniline 
• 109251-77-6 3-oxo-3-phenyl-propionic acid-(2-dimethylamino-anilide) 
• 124420-89-9 1-(2-Dimethylamino-phenyl)-3-pyridin-4-yl-urea 
• 29547-82-8 4-Cyano-2'-(N_.N-dimethylamino)-diphenylamin 
• 269412-22-8 2-Me₂NC₆H₄NMg*THF 
• 696605-19-3 N-[2-(N,N-dimethylamino)phenyl]-2-[(phenylmethoxy)carbonylamino]ethanamide 
• 1157841-03-6 N,N-dimethyl-N'-pyridin-2-ylmethylbenzene-1,2-diamine 
• 1402046-02-9 N-(2-dimethylaminophenyl)-N-pyridin-2-ylmethylbenzamide 
• 1033772-51-8 [(MeNN₂)NiPh] 
• 1033772-47-2 [((Me)NN₂)NiCl] 

Relevant academic research and scientific papers

Two-photon "caging" groups: Effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups

High two-photon photolysis cross sections and water solubility of probes are important to avoid toxicity in biomedical applications of photolysis. Systematic variation of the position of a carboxyl electron-withdrawing group (EWG) on photolysis of 8-dimet

Synthetic fosmidomycin analogues with altered chelating moieties do not inhibit 1-deoxy-d-xylulose 5-phosphate reductoisomerase or Plasmodium falciparum growth in vitro

Fourteen new fosmidomycin analogues with altered metal chelating groups were prepared and evaluated for inhibition of E. coli Dxr, M. tuberculosis Dxr and the growth of P. falciparum K1 in human erythrocytes. None of the synthesized compounds showed activ

Tert-amino effect-promoted rearrangement of aryl isothiocyanate: A versatile approach to benzimidazothiazepines and benzimidazothioethers

A general and practical approach to benzimidazothiazepine and benzimidazothioether derivatives via an intramolecular nucleophilic addition/ring expansion rearrangement of aryl isothiocyanates promoted by the tert-amino effect has been developed. This reaction is catalyzed by low-cost camphorsulfonic acid and tolerates a broad substrate scope with complete atom economy. Structurally intriguing benzimidazothiazepine and benzimidazothioether products could be easily obtained by a simple operation in good to excellent yield (up to 98%).

Zinc Chloride Complexes with Aliphatic and Aromatic Guanidine Hybrid Ligands and Their Activity in the Ring-Opening Polymerisation of d,l-Lactide

The synthesis of the new hybrid guanidine ligands DMEGdmap, DMEGdeae, TMGdmab, DMEGdmab, TMGdeab and DMEGdeab is reported. These ligands were combined with zinc chloride, and the six obtained new complexes were structurally characterised by X-ray crystall

A 3-fluoro-N-dimethyl O-phenylenediamine method for the synthesis of

The invention discloses a synthesis method of 3-fluoro-N-dimethyl o-phenylenediamine. The method comprises the following steps: with ortho-nitroaniline as a raw material, carrying out base catalysis on o-phenylenediamine and diethyl sulfate at the molar ratio of 1 to 2 by virtue of sodium bicarbonate for 2 hours at the pH value of 8 and the reaction temperature of 20-22 DEG C, so as to prepare N-dimethyl o-phenylenediamine; enabling N-dimethyl o-phenylenediamine to fully react with a fluoride solution under the action of a Pt/C catalyst; and washing, carrying out phase splitting and reduced pressure desolventizing, and drying to obtain 3-fluoro-N-dimethyl o-phenylenediamine, wherein the yield reaches over 87%.

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

Transition-metal-free access to primary anilines from boronic acids and a common +NH2 equivalent

Diversely substituted anilines are prepared by treatment of functionalized arylboronic acids with a common, inexpensive source of electrophilic nitrogen (H2N-OSO3H, HSA) under basic aqueous conditions. Electron-rich substrates are found to be the most reactive by this method. However, even moderately electron-poor substrates are well tolerated under the room temperature conditions. Sterically hindered substrates appear to be equally effective compared to unhindered ones. Highly electron-deficient substrates afford product in very low yields at room temperature, but moderate to good yields are obtained at refluxing temperatures. Our method is also amenable to electrophilic amination of several common boronic acid derivatives (e.g., pinacol esters). We demonstrate that it can be combined with metal-halogen exchange reactions or a variety of directed ortho metalation protocols in a "one-pot" sequence for the synthesis of aromatic amines with unique substitution patterns. DFT studies, in combination with experimental results, suggest that the reaction occurs via base-mediated activation of HSA, followed by 1,2 aryl B-N migration. This mode of activation appears to be critical for the success of the reaction and allows, for the first time, a general, electrophilic amination of boronic acids at ambient temperature.

Substitution effect on the one- and two-photon sensitivity of DMAQ "caging" groups

The systematic SAR study of a "caging" group showed a strong influence of the position of the donor dimethylamino group on the efficiency of photolysis of the DMAQ (2-hydroxymethylene-(N,N-dimethylamino)quinoline) caged acetate under one-photon near-UV or two-photon near-IR excitation. Photorelease of l-glutamate by the most efficient 8-DMAQ derivative strongly and efficiently activated glutamate receptors, generating large, fast rising responses similar to those elicited by glutamate photoreleased from the widely used MNI-caged glutamate.

Pd, Pt, and Ru complexes of a pincer bis(amino)amide ligand

An improved synthesis of pincer ligand bis[(2-dimethylamino)phenyl]amine (MeN2NH) was reported. Reaction of the Li complex of MeN2N with suitable Pd, Pt, and Ru precursors gave the corresponding metal complexes. The structures of the Pd, Pt, and Ru complexes were determined. The Ru complex showed activity in catalytic transfer hydrogenation of aryl and alkyl ketones. The Royal Society of Chemistry 2011.