(-)-Bis[(S)-1-phenylethyl]amine

Base Information

• Chemical Name: (-)-Bis[(S)-1-phenylethyl]amine
• CAS No.: 56210-72-1
• Molecular Formula: C₁₆H₁₉N
• Molecular Weight: 225.334
• Hs Code.: 2921199990
• UNII: 53L8SW1PN2,5D97T2Y7WU
• DSSTox Substance ID: DTXSID00426403
• Nikkaji Number: J629.745E
• Wikidata: Q72446754
• Mol file: 56210-72-1.mol

Synonyms:56210-72-1;(-)-Bis[(S)-1-phenylethyl]amine;bis[(s)-1-phenylethyl]amine;(1S)-1-phenyl-N-[(1S)-1-phenylethyl]ethanamine;Bis((S)-1-phenylethyl)amine;53L8SW1PN2;5D97T2Y7WU;(S,S)-Di(1-phenylethyl)amine;21003-56-5;(-)-Bis((S)-1-phenylethyl)amine;(S,S)-N,N-Bis(1-phenylethyl)amine;(1S)-1-Phenyl-N-((1S)-1-phenylethyl)ethanamine;(-)-Bis((S)-alpha-methylbenzyl)amine;(-)-Bis[(S)-alpha-methylbenzyl]amine;(S)-bis((S)-1-phenylethyl)amine;(S-(R*,R*))-(-)-Bis(alpha-methylbenzyl)amine;[S-(R*,R*)]-(-)-Bis(alpha-methylbenzyl)amine;MFCD00243087;Bis(alpha-methylbenzyl)amine, (+/-)-;UNII-53L8SW1PN2;UNII-5D97T2Y7WU;SCHEMBL3749295;DTXSID00426403;(S,S)-Bis(alpha-methylbenzyl)amine;AC1176;Bis(alpha-methylbenzyl)amine, (-)-;AKOS015915735;(-)-alpha,alpha'-Dimethyldibenzylamine;(S,S)-alpha,alpha'-Dimethyldibenzylamine;CS-11520;(-)-Bis[(S)-1-phenylethyl]amine, 99%;CS-0108759;(-)-Bis[(S)-1-phenylethyl]amine, ChiPros?;(S,S)-BIS(.ALPHA.-METHYLBENZYL)AMINE;BIS(.ALPHA.-METHYLBENZYL)AMINE, (-)-;(-)-BIS((S)-.ALPHA.-METHYLBENZYL)AMINE;Dibenzylamine, alpha,alpha'-dimethyl-, (+/-)-;A905791;BIS(.ALPHA.-METHYLBENZYL)AMINE, (+/-)-;(-)-.ALPHA.,.ALPHA.'-DIMETHYLDIBENZYLAMINE;(S,S)-.ALPHA.,.ALPHA.'-DIMETHYLDIBENZYLAMINE;(S)--Methyl-N-[(1S)-1-phenylethyl]benzenemethanamine;(|AS)-|A-Methyl-N-[(1S)-1-phenylethyl]benzenemethanamine;(S-(R*,R*))-(-)-BIS(.ALPHA.-METHYLBENZYL)AMINE;DIBENZYLAMINE, .ALPHA.,.ALPHA.'-DIMETHYL-, (+/-)-;Benzenemethanamine, alpha-methyl-N-(1-phenylethyl)-, (R*,R*)-;BENZENEMETHANAMINE, .ALPHA.-METHYL-N-(1-PHENYLETHYL)-, (R*,R*)-;Benzenemethanamine, alpha-methyl-N-((1R)-1-phenylethyl)-, (alphaR)-rel-;Benzenemethanamine, alpha-methyl-N-((1S)-1-phenylethyl)-, (alphaS)-;BENZENEMETHANAMINE, .ALPHA.-METHYL-N-((1R)-1-PHENYLETHYL)-, (.ALPHA.R)-REL-;BENZENEMETHANAMINE, .ALPHA.-METHYL-N-((1S)-1-PHENYLETHYL)-, (.ALPHA.S)-

Chemical Property of (-)-Bis[(S)-1-phenylethyl]amine

Chemical Property:

• Vapor Pressure: 0.00143mmHg at 25°C
• Melting Point: ~260 °C
• Refractive Index: n20/D 1.5525(lit.)
• Boiling Point: 86 ºC (0.05 mmHg)
• PKA: 8.79±0.29(Predicted)
• Flash Point: 113 ºC
• PSA: 12.03000
• Density: 0.987
• LogP: 4.48930
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility.: Immiscible with water.
• 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[(S)-1-phenylethyl]amine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)NC(C)C2=CC=CC=C2
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)N[C@@H](C)C2=CC=CC=C2
• Uses: (-)-Bis[(S)-1-phenylethyl]amine is used as a chiral resolution reagent in organic synthesis.

Technology Process of (-)-Bis[(S)-1-phenylethyl]amine

There total 89 articles about (-)-Bis[(S)-1-phenylethyl]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:

ethyl (S,S)-(-)-N,N-bis(α-methylbenzyl)glycinate

ethyl (R,R)-(+)-N,N-bis(α-methylbenzyl)glycinate

(S)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-[(1R)-1-phenethyl]amine

diphenyl-N,N-bis-((S,S)-1-phenyl-ethyl)phosphinamine

Refernces

• 1、 -. "Method for synthesizing chiral phosphite ligand based on R - 2 - phenylethylamine". . . Retrieved 2021/10/27.
• 2、 -. "Preparation method of chiral amine compounds". Paragraph 0018. . Retrieved 2018/09/13.