552-82-9

Basic information

• Product Name: N-Methyldiphenylamine
• Synonyms: N-METHYLDIPHENYLAMINE;N,N-DIPHENYL METHYLAMINE;Benzenamine,N-methyl-N-phenyl;Demelverine;Diphenylamine, N-methyl-;Diphenylmethylamine;Methyldiphenylamine;methyl-diphenyl-amine
• CAS NO: 552-82-9
• Molecular Formula: C₁₃H₁₃N
• Molecular Weight: 183.25
• EINECS: 209-023-2
• Product Categories: Intermediates of Dyes and Pigments;Amines;C11 to C38;Nitrogen Compounds;Building Blocks;C13;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 552-82-9.mol
• Article Data: 189

Chemical Properties

• Melting Point: -7.6 °C
• Boiling Point: 293 °C(lit.)
• Flash Point: 230 °F
• Appearance: White to beige/Crystalline Powder
• Density: 1.05 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00143mmHg at 25°C
• Refractive Index: n20/D 1.623(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 1.00±0.20(Predicted)
• Water Solubility: INSOLUBLE
• Merck: 14,6054
• CAS DataBase Reference: N-Methyldiphenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyldiphenylamine(552-82-9)
• EPA Substance Registry System: N-Methyldiphenylamine(552-82-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 552-82-9(Hazardous Substances Data)

Usage

Description

N-Methyldiphenylamine, an aromatic tertiary amine, is a clear yellow liquid that undergoes a photochemical reaction to transform into N-methylcarbazole (C). It is known for its applications in various industries due to its unique chemical properties.

Uses

Used in Chemical Synthesis:
N-Methyldiphenylamine is used as a starting reagent for the preparation of bis(4-carboxyphenyl)-N-methylamine (H2CPMA), which is essential in the synthesis of phosphonium ion salts. This application highlights its importance in the field of chemical synthesis and the production of specific compounds.
Used in Dye Manufacturing:
In the dye industry, N-Methyldiphenylamine is utilized in the manufacture of dyes, taking advantage of its chemical properties to create a range of colorants for various applications.
Used as a Reagent:
Similar to diphenylamine, N-Methyldiphenylamine serves as a reagent in the chemical and pharmaceutical industries. Its reactivity and stability make it a valuable component in various laboratory procedures and industrial processes.

Hazard

Toxic by ingestion.

InChI:InChI=1/C13H13N/c1-14(12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11H,1H3/p+1

Upstream product

• 21905-92-0 tetra-N-phenyl-methylenediamine 
• 100-61-8 N-methylaniline 
• 637-88-7 1,4-Cyclohexanedione 
• 57589-23-8 N-<(phenylthio)methyl>diphenylamine 
• 67-56-1 methanol 
• 122-39-4 diphenylamine 
• 71-43-2 benzene 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 66950-63-8 phenyl N,N-dimethylsulfamate 
• 108-95-2 phenol 
• 124-38-9 carbon dioxide 
• 121-69-7 N,N-dimethyl-aniline 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 105-07-7 4-cyanobenzaldehyde 

Downstream Products

• 68258-04-8 N-methyl-N-phenylaniline N-oxide 
• 38573-62-5 bis(2,4-dibromophenyl)amine 
• 3666-95-3 N-methyl-2,2',4,4'-tetrabromodiphenylamine 
• 6052-39-7 N-methyldiphenylamine-4-sulfonic acid 
• 55489-38-8 4-(methyl(phenyl)amino)benzaldehyde 
• 53158-79-5 4-nitroso-N-methyl-N,N-diphenylamine 
• 20799-61-5 bis(4-bromophenyl)-N-methylamine 
• 27164-41-6 N,N′-dimethyl-N,N′-diphenylbenzidine 
• 79159-85-6 bis-[4-(N-methyl-anilino)-phenyl]-diazene 
• 86-74-8 9H-carbazole 
• 100-47-0 benzonitrile 
• 122-39-4 diphenylamine 
• 62-53-3 aniline 
• 131-73-7 Dipikrylamin 

Relevant articles and documents

Double Ligands Enabled Ruthenium Catalyzed ortho-C?H Arylation of Dialkyl Biarylphosphines: Straight and Economic Synthesis of Highly Steric and Electron-Rich Aryl-Substituted Buchwald-Type Phosphines

A double-ligands enabled ruthenium catalyzed C(sp2)?H arylation of dialkyl phosphines is described, which provides a straight access to aryl-substituted dialkyl phosphine ligands. The combination of 1,3-diketone and amino acid ligands is essential for this transformation. An important six-membered cycloruthenium intermediate was successfully isolated and characterized by X-ray diffraction. Mechanistic studies showed that the 1,3-diketone promoted the process of oxidative addition of cycloruthenium intermediate. Some of modified CyJohnPhos ligands exhibited highly catalytic activity in palladium catalyzed C?N bond formation. (Figure presented.).

Effect of Precatalyst Oxidation State in C-N Cross-Couplings with 2-Phosphinoimidazole-Derived Bimetallic Pd(I) and Pd(II) Complexes

We report the catalytic activity of two phosphinoimidazole-derived bimetallic palladium complexes in Pd-catalyzed amination reactions. Our studies demonstrate that the starting oxidation state (Pd(I) or Pd(II)) of the dimeric complex has a significant effect on the efficiency of the catalytic reaction. The corresponding Pd(I) complex shows higher reactivity in Buchwald-Hartwig aminations, while the Pd(II) complex is much more reactive in carbonylative amination reactions. These new dimeric palladium complexes provide good to excellent reactivity and yields in the amination reactions tested.

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).