(+)-Bis[(R)-1-phenylethyl]amine

Base Information

• Chemical Name: (+)-Bis[(R)-1-phenylethyl]amine
• CAS No.: 23294-41-9
• Molecular Formula: C₁₆H₁₉N
• Molecular Weight: 225.334
• Hs Code.: 2921499090
• UNII: 72S7Q417U4
• DSSTox Substance ID: DTXSID501310198
• Nikkaji Number: J484.981G
• Wikidata: Q27266092
• Mol file: 23294-41-9.mol

Synonyms:(+)-Bis[(R)-1-phenylethyl]amine;23294-41-9;Bis[(R)-1-phenylethyl]amine;(1R)-1-phenyl-N-[(1R)-1-phenylethyl]ethanamine;(R,R)-Whitesell amine;Bis((R)-alpha-methylbenzyl)amine;rel-Bis((R)-1-phenylethyl)amine;Benzenemethanamine, alpha-methyl-N-[(1R)-1-phenylethyl]-, (alphaR)-;(+)-Bis((R)-1-phenylethyl)amine;(R,R)-Bis(alpha-methylbenzyl)amine;72S7Q417U4;BIS[(1R)-1-PHENYLETHYL]AMINE;42287-48-9;(r,r)-bis-(1-phenylethyl)amin;(+)-Bis((R)-alpha-methylbenzyl)amine;(+)-Bis[(R)-alpha-methylbenzyl]amine;MFCD00243088;Benzenemethanamine, alpha-methyl-N-((1R)-1-phenylethyl)-, (alphaR)-;(R)-Bis((R)-1-phenylethyl)amine;starbld0008186;SCHEMBL1200137;UNII-72S7Q417U4;(+)-bis(alpha-methylbenzyl)amine;DTXSID501310198;rac-bis[(1R)-1-phenylethyl]amine;AMY25620;Bis(alpha-methylbenzyl)amine, (+)-;AKOS024256880;CS-11207;(+)-Bis[(R)-1-phenylethyl]amine, 99%;BIS((R)-.ALPHA.-METHYLBENZYL)AMINE;(+)-Bis[(R)-1-phenylethyl]amine, ChiPros?;(R,R)-BIS(.ALPHA.-METHYLBENZYL)AMINE;BIS(.ALPHA.-METHYLBENZYL)AMINE, (+)-;EN300-100621;(+)-BIS((R)-.ALPHA.-METHYLBENZYL)AMINE;EN300-7440429;(R-(R*,R*))-(+)-Bis(alpha-methylbenzyl)amine;J-015069;Q27266092;(R-(R*,R*))-(+)-BIS(.ALPHA.-METHYLBENZYL)AMINE;(alphaR)-alpha-Methyl-N-((1R)-1-phenylethyl)benzenemethanamine;(.ALPHA.R)-.ALPHA.-METHYL-N-((1R)-1-PHENYLETHYL)BENZENEMETHANAMINE;BENZENEMETHANAMINE, .ALPHA.-METHYL-N-((1R)-1-PHENYLETHYL)-, (.ALPHA.R)-

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

Chemical Property:

• Vapor Pressure: 0.00143mmHg at 25°C
• Melting Point: ~260 °C
• Refractive Index: n20/D 1.5523(lit.)
• Boiling Point: 296.5 °C at 760 mmHg
• PKA: 8.79±0.29(Predicted)
• Flash Point: 137.2 °C
• PSA: 12.03000
• Density: 0.995 g/cm³
• LogP: 4.48930
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility.: Insoluble in 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[(R)-1-phenylethyl]amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• 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[(R)-1-phenylethyl]amine play a very extensive role of making chirally optically active drugs and compounds. Also as intermediates. (+)-Bis[(R)-1-phenylethyl]amine can be used:In the synthesis of?β-amino acids.In the preparation of chiral C(19)-C(26) and C(27)-C(32) moieties of scytophycin C.To induce enantioselectivity in the deprotonation of prochiral ketones.As a starting material for the synthesis of chiral phenolate ligands through Mannich condensation reaction.In the synthesis of chiral phosphoramidite ligands.To prepare chiral cyclic isoimidium salts, which are further used to synthesize chiral lactones through Diels-Alder reaction.

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

There total 89 articles about (+)-Bis[(R)-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:

N,N-bis-[(S)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine

2,2'-Bis-hexyloxy-[1,1']binaphthalenyl-6,6'-dicarboxylic acid bis-[bis-((R)-1-phenyl-ethyl)-amide]

(R*,R*)-N-(1'-phenylethyl)-1-phenylethylamine

(1S,1'S)-bis(1-phenylethyl)amine

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.