N-Methyldiphenylamine

Base Information

• Chemical Name: N-Methyldiphenylamine
• CAS No.: 552-82-9
• Deprecated CAS: 171745-65-6
• Molecular Formula: C13H13 N
• Molecular Weight: 183.253
• Hs Code.: 2921440000
• European Community (EC) Number: 209-023-2
• NSC Number: 3790
• UNII: B28ZGH99IH
• DSSTox Substance ID: DTXSID4060284
• Nikkaji Number: J37.748A
• Wikidata: Q27274274
• Mol file: 552-82-9.mol

Synonyms:N-Methyldiphenylamine;552-82-9;N-Methyl-N-phenylaniline;METHYLDIPHENYLAMINE;Benzenamine, N-methyl-N-phenyl-;Diphenylmethylamine;N,N-Diphenylmethylamine;Diphenylamine, N-methyl-;diphenylaminomethane;methyl-diphenyl-amine;N-Methy Ldipheny Lamine;NSC 3790;UNII-B28ZGH99IH;B28ZGH99IH;NSC-3790;EINECS 209-023-2;MFCD00041900;AI3-02479;N-methyl-N-phenyl-aniline;methyldiphenylamin;N-methyl diphenylamine;N-Methyldiphenyl-amine;N-Methyldiphenylamine, 96%;SCHEMBL31886;BIDD:GT0618;N-Methyl-N-phe-nylbenzenamine;SCHEMBL9054610;METHYLDIPHENYLAMINE [MI];DTXSID4060284;NSC3790;N-METHYL-N-PHENYLBENZENAMINE;AKOS005155810;CS-W017040;SY020107;AM20040703;FT-0632375;M0211;A830569;J-523673;W-105574;Q27274274

Chemical Property of N-Methyldiphenylamine

Chemical Property:

• Appearance/Colour: yellow oil-like liquid
• Vapor Pressure: 0.00143mmHg at 25°C
• Melting Point: -7.6 ºC
• Refractive Index: n20/D 1.623(lit.)
• Boiling Point: 296-297 ºC
• PKA: 1.00±0.20(Predicted)
• Flash Point: 116.6 ºC
• PSA: 3.24000
• Density: 1.05
• LogP: 3.45450
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: INSOLUBLE
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 183.104799419
• Heavy Atom Count: 14
• Complexity: 137

Purity/Quality:

98%, ^*data from raw suppliers

N-Methyldiphenylamine >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: CN(C1=CC=CC=C1)C2=CC=CC=C2
• Uses: manufacture of dyes; as reagent similar to diphenylamine. N-Methyldiphenylamine may be used for the synthesis of phosphonium ion salts. It may also be used as a starting reagent for the preparation of bis(4-carboxyphenyl)-N-methylamine (H2CPMA).

Technology Process of N-Methyldiphenylamine

There total 103 articles about N-Methyldiphenylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

chlorobenzene (108-90-7) + N-methylaniline (100-61-8) → benzhydrylidene(methyl)amine (552-82-9)

Guidance literature:

With [Pd(IPr*)(acac)Cl]; lithium hexamethyldisilazane; In 1,4-dioxane; at 110 ℃; for 3h; Inert atmosphere;

DOI:10.1021/om300205c

Reference yield: 99.0%

bromobenzene (108-86-1,52753-63-6) + N-methylaniline (100-61-8) → benzhydrylidene(methyl)amine (552-82-9)

Guidance literature:

With [Pd(IPr*)(acac)Cl]; lithium hexamethyldisilazane; In 1,4-dioxane; at 50 ℃; for 18h; Inert atmosphere;

DOI:10.1021/om300205c

Reference yield: 96.0%

N-methyl-N-phenylaniline N-oxide (68258-04-8) → benzhydrylidene(methyl)amine (552-82-9)

Guidance literature:

With tris(bipyridine)ruthenium(II) dichloride hexahydrate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate; In acetonitrile; at 20 ℃; for 0.5h; chemoselective reaction; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.0c02805

upstream raw materials:

methanol

diphenylamine hydrochloride

diphenylformamide

ethyl diphenylcarbamate

Downstream raw materials:

N-nitrosodiphenylamine

N-methyl-N-phenylaniline N-oxide

(4‐(methyl(phenyl)amino)phenyl)(phenyl)methanone

2-(N-Methyl-N-phenylamino)-benzoic acid

Refernces

• 1、 Bhojgude, Sachin Suresh,Baviskar, Dnyaneshwar R.,Gonnade, Rajesh G.,Biju, Akkattu T.. "Three-Component Coupling Involving Arynes, Aromatic Tertiary Amines, and Aldehydes via Aryl-Aryl Amino Group Migration". . p. 6270 - 6273. Retrieved 2015.
• 2、 Chao, Jianbin,Guo, Zhiqiang,Pang, Tengfei,Wei, Xuehong,Xi, Chanjuan,Yan, Leilei. "CO2-tuned highly selective reduction of formamides to the corresponding methylamines". supporting information. p. 7534 - 7538. Retrieved 2021/10/12.
• 3、 Wang, Liang-Neng,Tang, Pan-Ting,Li, Ming,Li, Jia-Wei,Liu, Yue-Jin,Zeng, Ming-Hua. "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". supporting information. p. 2843 - 2849. Retrieved 2021/05/03.