Bis(alpha-methylbenzyl)amine

Base Information

• Chemical Name: Bis(alpha-methylbenzyl)amine
• CAS No.: 10024-74-5
• Molecular Formula: C₁₆H₁₉N
• Molecular Weight: 225.334
• Hs Code.: 2921499090
• European Community (EC) Number: 631-165-2
• NSC Number: 13511
• DSSTox Substance ID: DTXSID20871198
• Nikkaji Number: J29.930H
• Mol file: 10024-74-5.mol

Synonyms:10024-74-5;Bis(1-Phenylethyl)Amine;1-phenyl-N-(1-phenylethyl)ethanamine;BIS(ALPHA-METHYLBENZYL)AMINE;alpha,alpha'-Dimethyldibenzylamine;Amine, diethyl, 1,1'-diphenyl;HSDB 2776;NSC 13511;Dibenzylamine, alpha,alpha'-dimethyl-;UNII-HZ2470VH5A;N,N-Bis(1-phenylethyl)amine;Bis(.alpha.-methylbenzyl)amine;Benzenemethanamine, alpha-methyl-N-(1-phenylethyl)-;Benzenemethanamine, .alpha.-methyl-N-(1-phenylethyl)-;ALPHA,ALPHA/'-DIMETHYLDIBENZYLAMINE;Dibenzylamine, .alpha.,.alpha.'-dimethyl-;(alphaS)-alpha-Methyl-N-[(1S)-1-phenylethyl]benzenemethanamine;MFCD00243087;MFCD00243088;starbld0009524;di-(1-Phenylethyl)-amine;bis(1-phenyl-ethyl)-amine;WLN: 1YR&MY1&R;Bis(.alpha.-phenylethyl)amine;SCHEMBL283979;HZ2470VH5A;Dibenzylamine,.alpha.'-dimethyl-;DTXSID20871198;(-)-Bis(alpha-methylbenzyl)amine;NSC13511;NSC-13511;AKOS000223231;AKOS017280350;SB79564;SB79579;SB79869;LS-61682;SY009312;SY023648;(2E)-3-(2-Aminopyrimidin-5-yl)acrylicacid;FT-0773190;FT-0773784;EN300-7437833

Chemical Property of Bis(alpha-methylbenzyl)amine

Chemical Property:

• Refractive Index: 1.5730
• Boiling Point: 296.5°Cat760mmHg
• Flash Point: 137.2°C
• PSA: 12.03000
• Density: 0.995g/cm³
• LogP: 4.48930
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 225.151749610
• Heavy Atom Count: 17
• Complexity: 180

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bis(1-Phenylethyl)amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: CC(C1=CC=CC=C1)NC(C)C2=CC=CC=C2

Technology Process of Bis(alpha-methylbenzyl)amine

There total 89 articles about Bis(alpha-methylbenzyl)amine 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: 98.0%

(αS)-α-methyl-N-(1-phenylethylidene)benzenemethanamine (40636-57-5) → (1S,1'S)-bis(1-phenylethyl)amine (21003-56-5,21003-57-6,23294-41-9,42287-48-9,56210-72-1,10024-74-5)

Guidance literature:

With N,N'-dimethyl-(R)-1,1'-binaphthyldiamine-bis-2-pyridinecarboxyamide; trichlorosilane; In dichloromethane; at 0 ℃; for 12h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol900945h

Reference yield: 91.0%

(S)-1-phenyl-ethylamine (2627-86-3) + acetophenone (98-86-2) → (1S,1'S)-bis(1-phenylethyl)amine (21003-56-5,21003-57-6,23294-41-9,42287-48-9,56210-72-1,10024-74-5)

Guidance literature:

(S)-1-phenyl-ethylamine; acetophenone; With tris(pentafluorophenyl)borate; In toluene; at 60 ℃; for 8h; Molecular sieve;

With ammonia borane; In toluene; at 0 ℃; for 12h; Solvent; Temperature; diastereoselective reaction; Molecular sieve;

DOI:10.1021/acs.joc.8b01362

Reference yield: 88.0%

acetophenone (98-86-2) → (R,R)-N,N-bis-(1-phenylethyl)amine (10024-74-5,21003-56-5,21003-57-6,23294-41-9,42287-48-9,56210-72-1)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; ammonium acetate; hydrogen; 2-((11bS)-2,6-di(naphthalen-1-yl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-1,2,3,4-tetrahydroisoquinoline; toluene-4-sulfonic acid; In methanol; dichloromethane; at 80 ℃; for 24h; under 45603.1 Torr; Reagent/catalyst; stereoselective reaction; Catalytic behavior; Autoclave;

DOI:10.1002/anie.202112671

upstream raw materials:

(αS)-α-methyl-N-(1-phenylethylidene)benzenemethanamine

2,2,6-trimethylcyclohexan-1-one

(S)-1-phenyl-ethylamine

N-benzylidene-(S)-α-methylbenzylamine

Downstream raw materials:

1,1-Bis-((R)-1-phenyl-ethyl)-urea

[(S,S)-bis(α-methylbenzyl)amino]phosphorous dichloride

O,O'-(1,1'-biphenyl-2,2'-diyl)-N,N'-bis[(S,S)-1-phenyl-ethyl]phosphoramidite

[(R)-1,1'-binaphthyl-2,2'-diyldioxy]{bis[(S)-(1-phenylethyl)]amino}phosphine

Refernces

• 1、 Farrell, Jeffrey M.,Heiden, Zachariah M.,Stephan, Douglas W.. "Metal-free transfer hydrogenation catalysis by B(C6F 5)3". . p. 4497 - 4500. Retrieved 2011.
• 2、 Yamaguchi, Ryohei,Mingwen, Zhu,Kawagoe, Shoko,Asai, Chiho,Fujita, Ken-Ichi. "A new atom-economical and selective synthesis of secondary and tertiary alkylamines by means of Cp*Iridium complex catalyzed multiple N-alkylation of ammonium salts with alcohols without solvent". . p. 1220 - 1223. Retrieved 2009.
• 3、 Boga, Carla,Savoia, Diego,Umani-Ronchi, Achille. "Diastereoselective Addition of Methylcopper- and Dimethylcuprate-Boron Trifluoride Reagents to (S)-(N-Alkylidene)-1-phenylethylamines". . p. 291 - 294. Retrieved 1990.
• 4、 Chang, Mingxin,Gao, Zhaofeng,Geng, Huiling,Huang, Haizhou,Liu, Jingwen. "An Iridium Catalytic System Compatible with Inorganic and Organic Nitrogen Sources for Dual Asymmetric Reductive Amination Reactions". supporting information. p. 27307 - 27311. Retrieved 2021/11/17.
• 5、 Muratov, Karim,Afanasyev, Oleg I.,Kuchuk, Ekaterina,Runikhina, Sofiya,Chusov, Denis. "One-Pot Synthesis of Symmetrical Tertiary and Secondary Amines from Carbonyl Compounds, Ammonium Carbonate and Carbon Monoxide as a Reductant". supporting information. p. 6557 - 6560. Retrieved 2019/10/22.