60539-17-5

Basic information

• Product Name: 2-Amino-1,1,2-triphenylethanol
• Synonyms: Benzeneethanol, b-aMino-a,a-diphenyl-
• CAS NO: 60539-17-5
• Molecular Formula: C₂₀H₁₉NO
• Molecular Weight: 289.37
• Mol File: 60539-17-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 456°C at 760 mmHg
• Flash Point: 229.6°C
• Appearance: /
• Density: 1.162g/cm³
• Vapor Pressure: 4.17E-09mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: 2-Amino-1,1,2-triphenylethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-1,1,2-triphenylethanol(60539-17-5)
• EPA Substance Registry System: 2-Amino-1,1,2-triphenylethanol(60539-17-5)

Safety Data

• Hazardous Substances Data: 60539-17-5(Hazardous Substances Data)

Usage

Also known as

(1R,2R)-2-amino-1,1,2-triphenylethanol or BPP

Properties

Chiral compound, non-selective beta-adrenergic antagonist

Usage

Ligand in asymmetric synthesis, precursor in synthesis of biologically active compounds

Chemical structure

Phenylethanolamine backbone with three phenyl groups attached to carbon atom, amino group attached to adjacent carbon atom

Potential applications

Pharmaceutical and chemical industries, chiral nature, building block for synthesis of complex molecules

InChI:InChI=1/C20H19NO/c21-19(16-10-4-1-5-11-16)20(22,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19,22H,21H2

Upstream product

• 119-61-9 benzophenone 
• 100-46-9 benzylamine 
• 873977-89-0 hippuric acid-(2-hydroxy-1,2,2-triphenyl-ethylamide) 
• 690629-64-2 N-benzylidene-2-methoxy-1-phenylethanamine 
• 1395342-20-7 2-(2-methoxy-1-phenylethylamino)-1,1,2-triphenylethanol 
• 100-52-7 benzaldehyde 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 
• 100-58-3 phenylmagnesium bromide 
• 875-74-1 (R)-phenylglycine 
• 108-86-1 bromobenzene 
• 157556-88-2 (S)-2,2,3-triphenyloxirane 
• 1395342-04-7 (R)-2-((S)-2-methoxy-1-phenylethylamino)-1,1,2-triphenylethanol 
• 862776-58-7 (S)-N-benzylidene-2-methylpropane-2-sulfinamide 

Downstream Products

• 62183-23-7 4,5,5-triphenyl-oxazolidin-2-one 
• 873977-89-0 hippuric acid-(2-hydroxy-1,2,2-triphenyl-ethylamide) 
• 119-61-9 benzophenone 
• 100-46-9 benzylamine 
• 21901-74-6 N-(2-hydroxy-1,2,2-triphenyl-ethyl)-acetamide 
• 153887-73-1 5-hydro-2,3-benzo-7-diphenil-8-1,4,6-threeoxa-9-aza-5-phospaspiro-<4.4>nonane 
• 156481-74-2 (R)-4-phenyl-5,5-diphenyl-oxazolidin-2-one 
• 1733-63-7 1,2,2-triphenylethan-1-one 

Relevant articles and documents

Addition of the Lithium Anion of Diphenylmethanol Methyl/Methoxymethyl Ether to Nonracemic Sulfinimines: Two-Step Asymmetric Synthesis of Diphenylprolinol Methyl Ether and Chiral (Diphenylmethoxymethyl)amines

Addition of the lithium anion generated from diphenylmethanol methyl and methoxymethyl ether to nonracemic sulfinimines afforded the corresponding addition products in excellent diastereoselctivity and yields. Deprotection of the MOM as well as sulfinyl groups rendered the enantiopure (diphenylhydroxymethyl)amines in excellent yields. The procedure was applied for a two-step synthesis of diphenylprolinol, a privileged ligand in asymmetric catalysis.

Titanium-mediated cross-coupling reactions of imines with ketones or aldehydes: An efficient route for the synthesis of 1,2-amino alcohols

The cross-coupling reactions of imines with ketones using Ti(O iPr)4/c-C5H9MgCl reagent lead to 1,2-amino alcohols after hydrolysis. The coupling reactions with aldehydes could also afford 1,2-amino alcohols, however, in some cases, aziridines were obtained as major products in a stereoselective manner.

Synthesis of heavily substituted 1,2-amino alcohols in enantiomerically pure form

A simple and convenient methodology for the preparation of optically pure 2-amino-2-aryl-1,1-diphenylethanols is presented. Allylamine was found to produce the ring-opening of triaryloxiranes in a regioselective and a stereospecific fashion. Removal of the allyl protecting group provided the free 1,2-amino alcohols in enantiomerically pure form.