86286-50-2

Basic information

• Product Name: (4R,5S)-(+)-CIS-4,5-DIPHENYL-2-OXAZOLIDINONE
• Synonyms: (4R,5S)-(+)-CIS-4,5-DIPHENYL-2-OXAZOLIDINONE;(4R,5S)-4,5-Diphenyl-2-oxazolidinone;(4R,5S)-cis-4,5-Diphenyloxazolidin-2-one;(4R,5S)-(+)-cis-4,5-Diphenyl-2-oxazolidinone, ee: 98%;(4R,5S)-4,5-Diphenyl-2-oxazolidinone,99%e.e.;(4R,5S)-4,5-DIPHENYLOXAZOLIDIN-2-ONE;(4R,5S)-(+)-cis-4,5-Diphenyl-2-oxazolidinone, 98%, ee: 98%
• CAS NO: 86286-50-2
• Molecular Formula: C₁₅H₁₃NO₂
• Molecular Weight: 239.27
• Product Categories: Benzene derivatives;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 86286-50-2.mol
• Article Data: 32

Chemical Properties

• Melting Point: 227-230 °C(lit.)
• Boiling Point: 466.6 °C at 760 mmHg
• Flash Point: 236 °C
• Appearance: /
• Density: 1.192 g/cm³
• Vapor Pressure: 6.98E-09mmHg at 25°C
• Refractive Index: 1.59
• PKA: 11.56±0.60(Predicted)
• CAS DataBase Reference: (4R,5S)-(+)-CIS-4,5-DIPHENYL-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S)-(+)-CIS-4,5-DIPHENYL-2-OXAZOLIDINONE(86286-50-2)
• EPA Substance Registry System: (4R,5S)-(+)-CIS-4,5-DIPHENYL-2-OXAZOLIDINONE(86286-50-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 86286-50-2(Hazardous Substances Data)

Usage

Preparation

To a stirred suspension of commercially available (10.0 g, 47 mmol) and triethylamine (14.4 mL, 0.10 mol) in dichloromethane (100 mL), diphosgene (3.0 mL, 25 mmol) was added dropwise at 0 °C and the mixture was stirred for 1 h at the same temperature. After concentration in vacuo, the residue was poured into water to precipitate crystals. The crystals were collected by filtration, successively washed with 10% HCl and H2O, and dried in vacuo at 50–60 °C for 3 h to afford 593a as colorless crystals (10.9 g, 97%).

InChI:InChI=1/C15H13NO2/c17-15-16-13(11-7-3-1-4-8-11)14(18-15)12-9-5-2-6-10-12/h1-10,13-14H,(H,16,17)/t13-,14+/m1/s1

Upstream product

• 54705-34-9 (1RS,2SR)-2-chloro-1,2-diphenyl-ethylamine; hydrochloride 
• 497-19-8 sodium carbonate 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 1439-07-2 trans-Stilbene oxide 
• 530-36-9 2-amino-1,2-diphenylethanol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 530-36-9 threo-1,2-diphenyl-2-aminoethan-1-ol 
• 503-38-8 trichloromethyl chloroformate 
• 146405-41-6 [2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethylidene]-trimethylsilanyl-amine 
• 591-51-5 phenyllithium 
• 163667-14-9 2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 169899-58-5 2-(1-hydroxy-1-phenylmethyl)-4,5-dimethylthiazole 
• 5908-41-8 benzoyltrimethylsilane 
• 98837-46-8 N-benzylidenediphenylphosphinamide 

Downstream Products

• 55041-24-2 3-amino-4r,5t-diphenyl-oxazolidin-2-one 
• 42746-66-7 3-nitroso-4r,5t-diphenyl-oxazolidin-2-one 
• 86217-59-6 (4R,5S)-cis-4,5-Diphenyl-2-oxazolidone-3-carbamyl Chloride 
• 142977-50-2 (4R,5S)-3-(1-methoxyethyl)-4,5-diphenyl-2-oxazolidinone 
• 176692-16-3 (4R,5S)-3-(2-Bromo-acetyl)-4,5-diphenyl-oxazolidin-2-one 
• 211043-74-2 ethyl ((4R,5S)-2-oxo-4,5-diphenyloxazolidin-3-yl)acetate 
• 259097-06-8 benzyl {[(4R,5S),1S]2S}-2-chloro-2-[1-(2-oxo-4,5-diphenyl-3-oxazolidinyl)-spiropentyl]acetate 
• 494841-74-6 (4R,5S)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-4,5-diphenyl-oxazolidin-2-one 
• 880767-53-3 (4R,5S)-3-acetyl-4,5-diphenyloxazolidin-2-one 
• 23204-71-9 (4R,5R)-trans-4,5-diphenyl-2-oxazolidinone 
• 170080-05-4 (4S,5S)-4,5-diphenyl-2-oxazolidinone 

Relevant articles and documents

Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases

Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative

Copper-Catalyzed Enantioselective Reductive Cross-Coupling of Aldehydes and Imines

A copper-catalyzed enantioselective reductive cross-coupling using aromatic aldehydes and imines, producing chiral β-amino alcohols, is described. The catalytic formation of enantioenriched chiral α-alkoxyalkylcopper(I) species from aromatic aldehydes and the subsequent reaction with imine electrophiles are attractive features of this protocol.

Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations

We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2–CSP 4).