173604-33-6

Basic information

• Product Name: (R)-(+)-4-(DIPHENYLMETHYL)-2-OXAZOLIDIN&
• Synonyms: (R)-(+)-4-(DIPHENYLMETHYL)-2-OXAZOLIDIN&;(R)-4-Methyldiphenyl-2-oxazolidinone;(R)-4-Methyl-3,4-diphenyloxazolidin-2-one;(R)-4-Benzhydryloxazolidin-2-one
• CAS NO: 173604-33-6
• Molecular Formula: C₁₆H₁₅NO₂
• Molecular Weight: 253.3
• Product Categories: Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 173604-33-6.mol

Chemical Properties

• Melting Point: 145-148 °C(lit.)
• Boiling Point: 472.603 °C at 760 mmHg
• Flash Point: 239.622 °C
• Appearance: /
• Density: 1.181 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: 2-8°C
• PKA: 12.29±0.40(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: (R)-(+)-4-(DIPHENYLMETHYL)-2-OXAZOLIDIN&(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-4-(DIPHENYLMETHYL)-2-OXAZOLIDIN&(173604-33-6)
• EPA Substance Registry System: (R)-(+)-4-(DIPHENYLMETHYL)-2-OXAZOLIDIN&(173604-33-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 173604-33-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-4-(Diphenylmethyl)-2-oxazolidinone is used as an organic chemical synthesis intermediate for the development of various pharmaceutical compounds. Its unique structure and chirality make it a promising candidate for the synthesis of enantiomerically pure drugs, which can have improved therapeutic effects and reduced side effects compared to their racemic counterparts.
Used in Chemical Research:
In the field of chemical research, (R)-(+)-4-(Diphenylmethyl)-2-oxazolidinone serves as a valuable intermediate for the synthesis of complex organic molecules and the study of asymmetric reactions. Its reactivity and structural features allow chemists to explore new synthetic pathways and develop innovative methodologies for the preparation of biologically active compounds and other specialty chemicals.
Used in Material Science:
(R)-(+)-4-(Diphenylmethyl)-2-oxazolidinone can also be utilized in material science for the development of novel polymers and materials with specific properties. Its incorporation into polymer backbones can lead to materials with improved mechanical, thermal, or biological properties, depending on the desired application.
Overall, (R)-(+)-4-(Diphenylmethyl)-2-oxazolidinone is a versatile and valuable intermediate in various fields, including pharmaceuticals, chemical research, and material science, due to its unique structure, reactivity, and potential for the development of enantiomerically pure compounds.

InChI:InChI=1/C16H15NO2/c18-16-17-14(11-19-16)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14-15H,11H2,(H,17,18)/t14-/m0/s1

Upstream product

• 173604-32-5 (S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one 
• 87727-28-4 (S)-2-tert-butyl-dimethyl-silanyloxy propanal 
• 176839-76-2 4-((R)-4-Benzhydryl-2-oxo-oxazolidin-3-yl)-4-oxo-butyric acid methyl ester 
• 74262-56-9 (2R)-2-(tert-butyldimethylsilyloxy)propanal 
• 312624-01-4 4-(diphenylmethyl)-2-oxazolidinone 
• 204851-65-0 (R)-2-Hydroxymethyl-3,3-diphenyl-propionic acid 

Downstream Products

• 183116-89-4 (R)-4-Benzhydryl-3-hexadecanoyl-oxazolidin-2-one 
• 175272-35-2 (4R,2'S)-N-(α-bromopropionyl)-2-oxazolidinone 
• 175023-96-8 (4R,2'R)-N-(α-bromopropionyl)-2-oxazolidinone 
• 187929-04-0 (E)-(4R)-3-(3-ethoxycarbonyl-2-propenoyl)-4-diphenyl-methyl-2-oxazolidinone 
• 898827-26-4 (R)-4-Benzhydryl-3-(2-methoxy-6-methyl-phenylethynyl)-oxazolidin-2-one 
• 1417575-40-6 C₁₉H₁₉NO₃ 
• 173604-34-7 (R)-4-Benzhydryl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 
• 1416129-73-1 C₂₃H₂₃NO₃ 
• 1253413-37-4 C₂₄H₂₃NO₅ 
• 155836-48-9 tert-butyl [(2R)-3-hydroxy-1,1-diphenylpropan-2-yl]carbamate 
• 143060-31-5 N-(tert-butoxycarbonyl)-3,3-diphenyl-D-alanine 
• 183253-63-6 (R)-4-Benzhydryl-3-{(R)-2-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-octadecanoyl}-oxazolidin-2-one 
• 183253-62-5 (R)-4-Benzhydryl-3-{(R)-2-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-hexadecanoyl}-oxazolidin-2-one 
• 183253-61-4 (R)-4-Benzhydryl-3-{(R)-2-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-7-methyl-octanoyl}-oxazolidin-2-one 

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

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).

A new route to 3-amino sugars. A concise synthesis of L-daunosamine and D-ristosamine derivatives

An asymmetric aldol strategy has been developed for the synthesis of L- daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O- TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two- step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similary, lactone 32 was converted to N- benzoylristosamide 42 with an overall yield of 18% starting from 12.

Synthesis of N-BOC-D-Diphenylalanine from L-Serine Methyl Ester Hydrochloride

A convenient six step synthesis of N-BOC-D-diphenylalanine from L-serine methyl ester hydrochloride is described.The preparation of a novel chiral auxiliary, an oxazolidinone derived from D-diphenylalaninol, is also described.