1205-39-6

Basic information

• Product Name: 2-METHYLDIPHENYLAMINE
• Synonyms: 2-METHYLDIPHENYLAMINE;2-Methyl-N-phenylaniline;2-Methyl-N-phenylbenzenamine;N-(2-Methylphenyl)benzenamine;N-Phenyl-2-methylaniline;Phenyl o-tolylamine
• CAS NO: 1205-39-6
• Molecular Formula: C₁₃H₁₃N
• Molecular Weight: 183.25
• Mol File: 1205-39-6.mol
• Article Data: 144

Chemical Properties

• Melting Point: 130-140 °C
• Boiling Point: 305 °C(Press: 727 Torr)
• Appearance: /
• Density: 1.066±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 0.65±0.20(Predicted)
• CAS DataBase Reference: 2-METHYLDIPHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLDIPHENYLAMINE(1205-39-6)
• EPA Substance Registry System: 2-METHYLDIPHENYLAMINE(1205-39-6)

Safety Data

• Hazardous Substances Data: 1205-39-6(Hazardous Substances Data)

Usage

General Description

2-Methyldiphenylamine is an organic compound that is commonly used as an antioxidant in various industrial applications. It belongs to the class of arylamines and is derived from aniline and methyl chloride. This chemical is primarily utilized as a stabilizer to prevent the degradation of polymers, such as rubber, plastics, and lubricants, caused by heat, oxygen, and metal ions. It functions by interrupting the oxidation process and inhibiting the formation of free radicals. Additionally, 2-Methyldiphenylamine is also used as an intermediate in the synthesis of dyes, pharmaceuticals, and other organic compounds. Despite its beneficial properties, this chemical may pose health hazards if not handled properly, and exposure should be minimized to prevent adverse effects on human health and the environment.

Upstream product

• 16610-44-9 2-[(2-methylphenyl)amino]benzoic acid 
• 158979-23-8 N-(2-methylphenyl)-N-phenylacetamide 
• 331464-99-4 N-phenyl-N-o-tolylbenzamide 
• 95-53-4 o-toluidine 
• 142-04-1 aniline hydrochloride 
• 100-65-2 N-Phenylhydroxylamine 
• 108-88-3 toluene 
• 622-37-7 Phenyl azide 
• 108-86-1 bromobenzene 
• 60-29-7 diethyl ether 
• 88-72-2 1-methyl-2-nitrobenzene 
• 95-49-8 2-methylchlorobenzene 
• 62-53-3 aniline 
• 95-46-5 2-methylphenyl bromide 

Downstream Products

• 260-94-6 acridine 
• 129574-38-5 N-(o-tolyl)-4-hydroxy-3-methyl-2(1H)-quinolone 
• 14185-37-6 N-(2-methylphenyl)cyclohexylamine 
• 6510-65-2 1-methyl-9H-carbazole 
• 158979-23-8 N-(2-methylphenyl)-N-phenylacetamide 
• 331464-99-4 N-phenyl-N-o-tolylbenzamide 
• 1233881-80-5 1-phenyl-2-(trifluoromethyl)-1H-indole 

Relevant articles and documents

Visible light-driven cross-coupling reactions at lower temperatures using a photocatalyst of palladium and gold alloy nanoparticles

Palladium (Pd)-catalyzed cross-coupling reactions are among the most important methods in organic synthesis. We report the discovery of highly efficient and green photocatalytic processes by which cross-coupling reactions, including Sonogashira, Stille, Hiyama, Ullmann, and Buchwald-Hartwig reactions, can be driven with visible light at temperatures slightly above room temperature using alloy nanoparticles of gold and Pd on zirconium oxide, thus achieving high yields. The alloy nanoparticles absorb visible light, and their conduction electrons gain energy, which is available at the surface Pd sites. Results of the density functional theory calculations indicate that transfer of the light excited electrons from the nanoparticle surface to the reactant molecules adsorbed on the nanoparticle surface activates the reactants. When the light intensity was increased, a higher reaction rate was observed, because of the increased population of photoexcited electrons. The irradiation wavelength also has an important impact on the reaction rates. Ultraviolet irradiation can drive some reactions with the chlorobenzene substrate, while visible light irradiation failed to, and substantially improve the yields of the reactions with the bromobenzene substrate. The discovery reveals the possibility of using low-energy and -density sources such as sunlight to drive chemical transformations.

Palladium-catalyzed one-pot diarylamine formation from nitroarenes and cyclohexanones

The first palladium-catalyzed diarylamine formation from nitroarenes and cyclohexanone derivatives using borrowed hydrogen is described. Various diarylamines were selectively obtained in good to excellent yields. The reaction tolerated a wide range of functionalities. The nitro reduction, cyclohexanone dehydrogenation, and imine formation and reduction were realized in a cascade without an external reducing reagent and oxidant.

Enolizable Ketones as Activators of Palladium(II) Precatalysts in Amine Arylation Reactions

Enolizable ketones have been identified as effective activators for palladium(II) precatalysts in the coupling of aryl bromides and aniline. N-arylation reactions catalyzed by [(DTBNpP)PdCl2]2 (DTBNpP = (bis(tert-butyl)neopentylphosphine) and PEPPSI-IPr precatalysts are activated by the addition of acetone, mesityl oxide, and 3-pentanone. 3-Pentanone was the most effective activator. Mechanistic studies show that acetone, 3-pentanone, and mesityl oxide reduce [(DTBNpP)PdCl2]2 in the presence of NaO-t-Bu to Pd0(DTBNpP)2

Pentavalent organoantimony compounds as mild N-arylating agents for amines: Cu-mediated ullmann-type N-arylation with tetraarylantimony(V) acetates

Simple and mild Cu-mediated arylation of various amines by use of tetraarylantimony acetate (Ar4SbOAc) is described. The Ullmann-type condensation of Ar4SbOAc with aliphatic and electron rich aromatic amines proceeded efficiently in

3-(Diphenylphosphino)propanoic acid: An efficient ligand for Cu-catalyzed N-arylations of indoles and aryl amines

3-(Diphenylphosphino)propanoic acid (L2) was found to be an efficient ligand for the copper-catalyzed N-arylations of indoles and arylamines with aryl iodides, the C-N coupling reactions catalyzed by CuCl/L2 were smoothly carried out in DMSO at 120 °C and give the corresponding products with the yields of 25-98 %.

Stable, Well-Defined Nickel(0) Catalysts for Catalytic C-C and C-N Bond Formation

The synthesis and catalytic activity of several classes of NHC-Ni(0) precatalysts stabilized by electron-withdrawing alkenes are described. Variations in the structure of fumarate and acrylate ligands modulate the reactivity and stability of the NHC-Ni(0) precatalysts and lead to practical and versatile catalysts for a variety of transformations. The catalytic activity and efficiency of representative members of this class of catalysts have been evaluated in reductive couplings of aldehydes and alkynes and in N-arylations of amines.

Aromatic Substitution by Phenylnitrenium and Naphthylnitrenium Ions formed from Phenyl Azide and 1-Azidonaphthalene in the Presence of Trifluoromethanesulphonic Acid

Aromatic N-substitution by phenylnitrenium ions generated from phenyl azide in the presence of a catalytic amount of trifluoromethanesulphonic acid gave diarylamines (in especially good yield in the reaction with biphenyl or naphthalene), whereas naphthylnitrenium ions from 1-azidonaphthalene react with benzene to afford a C-substitution product, 1-amino-4-phenylnaphthalene.

High Catalytic Activity of Peptide Nanofibres Decorated with Ni and Cu Nanoparticles for the Synthesis of 5-Substituted 1H-Tetrazoles and N-Arylation of Amines

A rapid development of a new methodology for decarboxylative N-arylation of carboxylic acids and the preparation of 5-substituted 1H-tetrazoles catalysed by peptide nanofibres decorated with Cu and Ni nanoparticles is presented. Compared with conventional aryl halides, benzoic acids are extremely interesting and environmentally friendly options for the synthesis of secondary aryl amines.

N-Heterocyclic Carbene Palladium(II) Amine Complexes: The Role of Primary Aryl- or Alkylamine Binding and Applications in the Buchwald-Hartwig Amination Reaction

N-heterocyclic carbene-palladium(II) amine complexes bearing primary aryl- or alkylamines were synthesized. The prepared complexes were characterized by single crystal X-ray diffraction as well as NMR spectroscopy. These complexes exhibited good catalytic activities for the Buchwald-Hartwig amination reaction of aryl chlorides to afford arylated anilines under mild conditions. All reactions were carried out in air and all starting materials were used as supplied without purification. 21 expected coupling products were obtained in moderate to high yields under optimum conditions.

Visible-Light- And PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature

We present here a metal-free, visible-light- and triphenylphosphine-mediated intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.

Diphenylamine derivative organic room-temperature phosphorescent compound as well as preparation method and application thereof

The present invention provides a diphenylamine derivative organic room temperature phosphorescent compound, which is characterized in that the structural formula of the diphenylamine derivative organic room temperature phosphorescent compound is represent