23190-16-1

Basic information

• Product Name: (1R,2S)-2-Amino-1,2-diphenylethanol
• Synonyms: (1R,2S)-(-)-2-AMINO-1,2-DIPHENYLETHANOL;(1R,2S)-2-AMINO-1,2-DIPHENYLETHANOL;(1R,2S)-(-)-DIPHENYL-2-AMINOETHANOL;(1R,2S)-(-)-ERYTHRO-2-AMINO 1,2-DIPHENYLETHANOL;BENZENEETHANOL, B-AMINO-A-PHENYL-, (AR,BS)-;(1R,2S)-(-)-amino-1,2,-diphenylethanol;(1R,2S)-(-)-2-Amino-1,2-dipenylethanol;(1R,2S)-(-)-1,2-DIPHENYLHYDROXYETHYLAMINE
• CAS NO: 23190-16-1
• Molecular Formula: C₁₄H₁₅NO
• Molecular Weight: 213.27
• Product Categories: chiral;Chiral reagent;Amino Alcohols (Chiral);Chiral Building Blocks;for Resolution of Acids;Optical Resolution;Synthetic Organic Chemistry;Amino Alcohols & Deriv.;CHIRAL CHEMICALS;Chiral Compound;Amino Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 23190-16-1.mol
• Article Data: 56

Chemical Properties

• Melting Point: 142-144 °C(lit.)
• Boiling Point: 261 °C at 760 mmHg
• Flash Point: 125.3 °C
• Appearance: white to light-yellow/Powder
• Density: 1.148 g/cm₃
• Vapor Pressure: 2.88E-06mmHg at 25°C
• Refractive Index: -7 ° (C=0.6, EtOH)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethanol, Methanol
• PKA: 11.70±0.45(Predicted)
• BRN: 2806218
• CAS DataBase Reference: (1R,2S)-2-Amino-1,2-diphenylethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-2-Amino-1,2-diphenylethanol(23190-16-1)
• EPA Substance Registry System: (1R,2S)-2-Amino-1,2-diphenylethanol(23190-16-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 23190-16-1(Hazardous Substances Data)

Usage

Description

(1R,2S)-2-Amino-1,2-diphenylethanol, also known as a hydroxylated 1,2-diphenethylamine derivative, is a chiral molecule with distinct stereochemistry. It exhibits affinity for the NMDA receptor and is characterized by its white to light yellow crystal powder appearance. (1R,2S)-2-Amino-1,2-diphenylethanol is known for its unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
(1R,2S)-2-Amino-1,2-diphenylethanol is used as a chiral auxiliary for Pd(II)-assisted chiral tandem alkylation and carbonylative coupling reactions. Its stereoselective nature makes it a valuable tool in the synthesis of complex organic molecules, particularly in the development of pharmaceutical compounds.
Used in Neuroscience Research:
As a compound with affinity for the NMDA receptor, (1R,2S)-2-Amino-1,2-diphenylethanol is used in neuroscience research to study the function and role of NMDA receptors in the central nervous system. This can lead to a better understanding of neurological disorders and the development of potential therapeutic agents.
Used in Chemical Synthesis:
(1R,2S)-2-Amino-1,2-diphenylethanol is also used as a key intermediate in the synthesis of various organic compounds, particularly those with chiral centers. Its unique structure allows for the creation of novel molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C14H15NO/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14,16H,15H2/t13-,14+/m0/s1

Upstream product

• 530-36-9 threo-1,2-diphenyl-2-aminoethan-1-ol 
• 618-65-5 helicin 
• 441-38-3 benzoin oxime 
• 574-15-2 benzilmonoxime 
• 780-25-6 N-benzylidene benzylamine 
• 169899-58-5 2-(1-hydroxy-1-phenylmethyl)-4,5-dimethylthiazole 
• 5908-41-8 benzoyltrimethylsilane 
• 131350-15-7 N-[(1R,2S)-2-hydroxy-1,2-diphenylethyl]formamide 
• 77539-19-6 2-benzyloxyimino-1,2-diphenylethane-1-one 
• 23412-95-5 dl-erythro-1,2-diphenyl-2-hydroxyethylamine 
• 120443-82-5 (R)-2-phenyl-2-(trimethylsiloxy)acetonitrile 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 572-45-2 benzil dioxime 
• 26114-25-0 cis-2,3-diphenylaziridine 

Downstream Products

• 92552-75-5 4,5-diphenyl-2-oxazolidinone 
• 6275-45-2 dichloro-acetic acid-(α'-hydroxy-bibenzyl-α-ylamide) 
• 530-36-9 (1R,2R)-2-amino-1,2-diphenylethane-1-ol 
• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 530-36-9 (1S,2S)-2-amino-1,2-diphenylethanol 
• 530-36-9 2-amino-1,2-diphenylethanol 
• 6287-74-7 (+/-)-erythro-α'-(2-diethylamino-ethylamino)-bibenzyl-α-ol 
• 23364-44-5 (1S,2R)-2-Amino-1,2-diphenylethanol 
• 530-36-9 threo-1,2-diphenyl-2-aminoethan-1-ol 
• 49855-40-5 (+/-)-erythro-α'-chloro-bibenzylyl-(α)-amine 
• 49855-40-5 (+/-)-threo-α'-chloro-bibenzylyl-(α)-amine 
• 780-25-6 N-benzylidene benzylamine 
• 100-52-7 benzaldehyde 
• 100-46-9 benzylamine 

Relevant articles and documents

Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols

This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of α-iminoketones for accessing chiral vicinal amino alcohols, which are privileged motifs in pharmaceuticals, agrochemicals, fine chemicals, chiral auxiliaries, organocatalysts, etc. Compared with existing methods, this methodology has the following advantages, such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields (90 to 96%) and stereoselectivities (up to >99:1 dr; >99.9% ee). In addition, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.

NOVEL METHOD FOR PREPARING (2R)-2-(2-METHOXYPHENYL)-2-(OXANE-4-YLOXY)ETHANE-1-OL COMPOUND, AND INTERMEDIATE USED THEREIN

A novel method for preparing a compound of Chemical Formula 1 is disclosed. The method includes a step of obtaining a compound of Chemical Formula 1 by performing a reduction reaction on a compound of Chemical Formula 2; and an intermediate used therein. According to the preparation method of the present invention, the compound of Chemical Formula 1, which is useful for the production of an acetyl-CoA carboxylase (ACC) inhibitor, can be mass-produced more simply and efficiently than that of a conventional method:

Large-scale preparation of key building blocks for the manufacture of fully synthetic macrolide antibiotics

Key building blocks for the production of fully synthetic macrolides have been scaled-up in first time pilot plant and kilo-lab campaigns. These building blocks have supported the discovery of new macrolide antibiotics as well as ongoing preclinical studies.