23364-44-5

Basic information

• Product Name: (1S,2R)-2-Amino-1,2-diphenylethanol
• Synonyms: (1S,2R)-(-)-2-AMINO-1,2-DIPHENYLETHANOL;(1S,2R)-(+)-2-AMINO-1,2-DIPHENYLETHANOL;(1S,2R)-2-AMINO-1,2-DIPHENYLETHANOL;(1S,2R)-(+)-DIPHENYL-2-AMINOETHANOL;(1R,2S)-(-)-ERYTHRO-2-AMINO 1,2-DIPHENYLETHANOL;(1R,2S)-(-)-DIPHENYL-2-AMINOETHANOL;BENZENEETHANOL, B-AMINO-A-PHENYL-, (AR,BS)-;BENZENEETHANOL, B-AMINO-A-PHENYL-, (AS,BR)-
• CAS NO: 23364-44-5
• Molecular Formula: C₁₄H₁₅NO
• Molecular Weight: 213.27
• EINECS: 1806241-263-5
• 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 chemicals;Chiral Compound;Benzene derivatives;Amino Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 23364-44-5.mol

Chemical Properties

• Melting Point: 142-144 °C(lit.)
• Boiling Point: 374.3 ºC at 760 mmHg
• Flash Point: 180.2 ºC
• Appearance: White to beige/Crystalline 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: very faint turbidity in Methanol
• PKA: 11.70±0.45(Predicted)
• BRN: 1212828
• CAS DataBase Reference: (1S,2R)-2-Amino-1,2-diphenylethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-2-Amino-1,2-diphenylethanol(23364-44-5)
• EPA Substance Registry System: (1S,2R)-2-Amino-1,2-diphenylethanol(23364-44-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• F: 9
• Hazardous Substances Data: 23364-44-5(Hazardous Substances Data)

Usage

Uses

(1S,2R)-2-Amino-1,2-diphenylethanol is used in various applications across different industries due to its unique properties and reactivity. Here are some of its uses:
1. Used in Catalyst Preparation:
(1S,2R)-2-Amino-1,2-diphenylethanol is used as a precursor to prepare vanadium(V) Schiff base complexes. These complexes serve as catalysts in the oxidation of sulfides and olefins, which are important reactions in the chemical industry for the synthesis of various products.
2. Used in Chiral Selectors for HPLC:
(1S,2R)-2-Amino-1,2-diphenylethanol is used to prepare chiral selectors, which are then immobilized on aminated silica gel. The resulting chiral stationary phase is applied in high-performance liquid chromatography (HPLC) for the separation of enantiomers, which is crucial in pharmaceutical research and development.
3. Used in Heterogeneous Catalysis:
(1S,2R)-2-Amino-1,2-diphenylethanol can be immobilized on the frame of α-zirconium phosphate to yield layered zirconium phosphonates. These materials are used in heterogeneous catalysis, providing an alternative to homogeneous catalysts and offering advantages such as ease of separation and reuse.
4. Used as a Chiral Auxiliary in Organic Synthesis:
(1S,2R)-2-Amino-1,2-diphenylethanol is employed as a chiral auxiliary in the preparation of homopropargylic alcohols from aliphatic and aromatic aldehydes. The use of (1S,2R)-2-Amino-1,2-diphenylethanol in this context helps to control the stereochemistry of the resulting products, which is essential for the development of enantiomerically pure pharmaceuticals and other chiral compounds.

Reaction

Ligand used to make chiral oxaborolidines for the enantioselective alkynylation of aldehydes Ligand used in organoindium reagents for asymmetric Barbier-type allylations Ligand used in organoindium reagents for asymmetric Barbier-type propargylations

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/p+1/t13-,14+/m1/s1

Upstream product

• 64-17-5 ethanol 
• 87-69-4 L-Tartaric acid 
• 530-36-9 threo-1,2-diphenyl-2-aminoethan-1-ol 
• 572-45-2 benzil dioxime 
• 618-65-5 helicin 
• 70981-26-9 α'-benzylidenamino-bibenzyl-α-ol 
• 441-38-3 benzoin oxime 
• 574-15-2 benzilmonoxime 
• 1689-71-0 2,3-diphenyloxirane 
• 7677-24-9 trimethylsilyl cyanide 
• 100-52-7 benzaldehyde 
• 780-25-6 N-benzylidene benzylamine 
• 169899-58-5 2-(1-hydroxy-1-phenylmethyl)-4,5-dimethylthiazole 
• 801219-76-1 2-(diphenylphosphinamide)-1,2-diphenylethanone 

Downstream Products

• 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 
• 84388-60-3 N-(α'-hydroxy-bibenzyl-α-yl)-acetamide 
• 70981-26-9 α'-benzylidenamino-bibenzyl-α-ol 
• 664371-11-3 α'-salicylidenamino-bibenzyl-α-ol 
• 93008-68-5 (1S,2S)-2-acetoxy-1,2-diphenyl-ethylamine 
• 93008-68-5 (1R,2R)-2-acetoxy-1,2-diphenyl-ethylamine 
• 7431-13-2 threo-2-acetamido-1,2-diphenylethan-1-ol 
• 51675-69-5 2,2,3,3-tetramethyl-7,8-diphenyl-1,4,6-trioxa-9-aza-5λ⁵-phospha-spiro[4.4]nonane 
• 51675-90-2 4',5'-diphenyl-2λ⁵-spiro[benzo[1,3,2]dioxaphosphole-2,2'-[1,3,2]oxazaphospholidine] 
• 142452-47-9 2,3-Diphenyl-1-oxa-4-aza-spiro[4.5]decane 
• 142452-50-4 2-Benzyl-4,5-diphenyl-oxazolidine 

Relevant articles and documents

Site-Specific C(sp3)–H Aminations of Imidates and Amidines Enabled by Covalently Tethered Distonic Radical Anions

The utilization of N-centered radicals to synthesize nitrogen-containing compounds has attracted considerable attention recently, due to their powerful reactivities and the concomitant construction of C?N bonds. However, the generation and control of N-centered radicals remain particularly challenging. We report a tethering strategy using SOMO-HOMO-converted distonic radical anions for the site-specific aminations of imidates and amidines with aid of the non-covalent interaction. This reaction features a remarkably broad substrate scope and also enables the late-stage functionalization of bioactive molecules. Furthermore, the reaction mechanism is thoroughly investigated through kinetic studies, Raman spectroscopy, electron paramagnetic resonance spectroscopy, and density functional theory calculations, revealing that the aminations likely involve direct homolytic cleavage of N?H bonds and subsequently controllable 1,5 or 1,6 hydrogen atom transfer.

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides

The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.

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.

Chiral morphine quinoline compound preparation method and chiral amino acid preparation method of compound

The invention provides chiral morpholine compounds. The structural general formula of the chiral morpholine compounds is as shown in the description. The invention further comprises a preparation method of the chiral morpholine compounds. The chiral morpholine compounds are prepared by using benzoin as a starting material, performing reductive amination, and performing chemical resolution on enantiomers and acid-catalyzed ester condensation reaction. The invention further provides amino acid compounds prepared from the chiral morpholine compounds, and a preparation method and application of the amino acid compounds.

Stereoretentive Addition of N-tert-Butylsulfonyl-α-Amido Silanes to Aldehydes, Ketones, α,β-Unsaturated Esters, and Imines

Enantioenriched N-tert-butylsulfonyl-α-amido silanes were successfully reacted with aldehydes, ketones, imines, and α,β-unsaturated esters in the presence of a sub-stoichiometric amount of CsF (0.5 equiv) in 1,2-dimethoxyethane (DME) at -20 °C to afford the corresponding coupling products with up to 89 % enantiospecificity in a retentive manner. Keep your cool! Enantioenriched N-tert-butylsulfonyl-α-amido silanes were successfully reacted with aldehydes, ketones, imines, and α,β-unsaturated esters in the presence of a sub-stoichiometric amount of CsF (0.5 equiv) in 1,2-dimethoxyethane (DME) at -20 °C to afford the corresponding coupling products with up to 89 % enantiospecificity in a retentive manner.

Highly enantioselective hydrogenation of o-alkoxy tetrasubstituted enamides catalyzed by a Rh/(R, S)-josiphos catalyst

Rh/(R,S)-JosiPhos complex-catalyzed asymmetric hydrogenation of o-alkoxy tetrasubstituted enamides has been achieved, and it furnished a set of β-amino alcohol analogues in high yields and excellent enantiomeric excesses (>99% conversion, up to 99% ee).This method provides valuable chiral building blocks in chiral pharmaceuticals and useful motifs for catalysts.

Enantioselective synthesis of diaryl aziridines using tetrahydrothiophene- based chiral sulfides as organocatalysts

This work describes catalytic and asymmetric aziridinations (15 examples, 95-98% ee) of benzyl bromide and imines via the imino Corey-Chaykovsky reaction using (thiolan-2-yl)diarylmethanol benzyl ether as an organocatalyst. The catalyst and analogues thereof were prepared through an expeditious and efficient synthetic route featuring a double nucleophilic substitution and Shi epoxidation as key steps.

Readily available ruthenium complex for efficient dynamic kinetic resolution of aromatic α-hydroxy ketones

A ruthenium complex formed from commercially available [Ru(p-cymene)Cl 2]2 and 1,4-bis(diphenylphosphino)butane catalyzes the racemization of aromatic α-hydroxy ketones very efficiently at room temperature. The racemization is fully compatible with a kinetic resolution catalyzed by a lipase from Pseudomonas stutzeri. This is the first example of dynamic kinetic resolution of α-hydroxy ketones at ambient temperature in which the metal and enzyme catalysts work in concert in one pot at room temperature to give quantitative yields of esters of α-hydroxy ketones with very high enantioselectivity.

HETEROARYL ACID MORPHOLINONE COMPOUNDS AS MDM2 INHIBITORS FOR THE TREATMENT OF CANCER

The present invention provides MDM2 inhibitor compounds of Formula (I), or the pharmaceutically acceptable salts thereof, wherein the variables are defined above, which compounds are useful as therapeutic agents, particularly for the treatment of cancers. The present invention also relates to pharmaceutical compositions that contain an MDM2 inhibitor of Formula (I).

Solvent-induced reversed stereoselectivity in reciprocal resolutions of mandelic acid and erythro -2-amino-1,2-diphenylethanol

Solvent-induced chirality switching in reciprocal optical resolution between mandelic acid (1) and erythro-2-amino-1,2-diphenylethanol (2) has been demonstrated. The stereochemistry of the deposited salts was controlled by changing the crystallization solvent from 1-PrOH or 1-BuOH to 1,4-dioxane. It was revealed from 1H NMR spectra, thermogravimetric analysis, and X-ray crystallography of the salts that an equimolar amount of the crystallization solvent was incorporated in each diastereomeric salt. On the basis of the crystal structures, it was found that both the hydrogen-bonding ability and the size of the solvent molecule played an important role. Differences in the formed hydrogen-bonding networks (columnar or sheetlike structure) and their packing manner were found to be crucial for the reversed stereoselectivity. Furthermore, pseudopolymorphic salt crystals that incorporated 1,4-dioxane were obtained during the enantioseparation of racemic 2, and their solid-state properties were examined by measurement of their IR spectra. This solvent-induced dual stereocontrol technique was successfully applied to the successive resolution process, eliminating the need to change the resolving agent for access to both enantiomers of 1 and 2.