N,N-Diphenyl-2-naphthylamine

Base Information

• Chemical Name: N,N-Diphenyl-2-naphthylamine
• CAS No.: 6940-30-3
• Molecular Formula: C22H17 N
• Molecular Weight: 295.384
• European Community (EC) Number: 811-067-8
• NSC Number: 37624
• DSSTox Substance ID: DTXSID80989223
• Nikkaji Number: J2.182.201I
• Wikidata: Q82978156
• Mol file: 6940-30-3.mol

Synonyms:n,n-diphenylnaphthalen-2-amine;6940-30-3;N,N-Diphenyl-2-naphthylamine;N,N-diphenyl-2-Naphthalenamine;NSC37624;SCHEMBL1035098;DTXSID80989223;ADAL1088125;MFCD28384144;NSC-37624;N-phenyl-2-N-phenyl-2-naphthalamine;D4843;T71240

Chemical Property of N,N-Diphenyl-2-naphthylamine

Chemical Property:

• Vapor Pressure: 2.08E-08mmHg at 25°C
• Melting Point: 123.0 to 127.0 °C
• Boiling Point: 453.4°Cat760mmHg
• Flash Point: 200.8°C
• PSA: 3.24000
• Density: 1.159g/cm³
• LogP: 6.30960
• Solubility.: soluble in Toluene
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 295.136099547
• Heavy Atom Count: 23
• Complexity: 335

Purity/Quality:

99.80% ^*data from raw suppliers

N,N-Diphenylnaphthalen-2-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N(C2=CC=CC=C2)C3=CC4=CC=CC=C4C=C3
• Uses: N,N-Diphenylnaphthalen-2-amine is used as a reactant in the synthesis of biaryl diamines.

Technology Process of N,N-Diphenyl-2-naphthylamine

There total 15 articles about N,N-Diphenyl-2-naphthylamine 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%

2-bromonaphthalene (580-13-2) + N-(trimethylsilyl)-diphenylamine (17425-91-1) → 2-(N,N-diphenylamino)naphthalene (6940-30-3)

Guidance literature:

With cesium fluoride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; XPhos; at 100 ℃; for 1h; Inert atmosphere;

DOI:10.1246/cl.131075

Reference yield: 91.0%

2-iodonaphthalene (612-55-5) + diphenylamine (122-39-4) → 2-(N,N-diphenylamino)naphthalene (6940-30-3)

Guidance literature:

diphenylamine; With butyl magnesium bromide; In 2-methyltetrahydrofuran; at 20 ℃; for 3h;

2-iodonaphthalene; In 2-methyltetrahydrofuran; 1,3,5-trimethyl-benzene; at 185 ℃; for 72h; Reagent/catalyst;

DOI:10.1002/chem.201800011

Reference yield: 90.0%

2-bromonaphthalene (580-13-2) + diphenylamine (122-39-4) → 2-(N,N-diphenylamino)naphthalene (6940-30-3)

Guidance literature:

diphenylamine; With ethylmagnesium bromide; In diethyl ether; at 0 - 40 ℃; for 2h; Inert atmosphere;

2-bromonaphthalene; With lithium bromide; iron(II) chloride; In 5,5-dimethyl-1,3-cyclohexadiene; at 140 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ja309845k

upstream raw materials:

N-Phenyl-2-naphthylamine

1,4-Cyclohexanedione

iodobenzene

bromobenzene

Downstream raw materials:

7-phenyl-benzo[a]acridinium perchlorate

N,N,N′,N′-tetraphenyl-1,1′-binaphthalene-2,2′-diamine

Refernces

• 1、 Kiriyama, Kazuya,Okura, Keisho,Tamakuni, Fumiko,Shirakawa, Eiji. "Electron-Catalyzed Coupling of Magnesium Amides with Aryl Iodides". supporting information. p. 4519 - 4522. Retrieved 2018/03/13.
• 2、 Minami, Yasunori,Komiyama, Takeshi,Shimizu, Kenta,Hiyama, Tamejiro,Goto, Osamu,Ikehira, Hideyuki. "Catalytic carbon-nitrogen bond-forming cross-coupling using N-trimethylsilylamines". . p. 1437 - 1446. Retrieved 2015/11/16.