191090-29-6

Basic information

• Product Name: (S)-(-)-5 5-DIPHENYL-4-METHYL-2-OXAZOLI&
• Synonyms: (S)-(-)-5 5-DIPHENYL-4-METHYL-2-OXAZOLI&;(S)-(-)-5,5-DIPHENYL-4-METHYL-2-OXAZOLID;(S)-4-Methyl-5,5-diphenyloxazolidin-2-one;(S)-5,5-Diphenyl-4-methyl-2-oxazolidinone,99%e.e.;(4S)-4-methyl-5,5-diphenyl-1,3-oxazolidin-2-one
• CAS NO: 191090-29-6
• Molecular Formula: C₁₆H₁₅NO₂
• Molecular Weight: 253.299
• Product Categories: Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 191090-29-6.mol

Chemical Properties

• Melting Point: 263-267 °C(lit.)
• Boiling Point: 464.953 °C at 760 mmHg
• Flash Point: 234.995 °C
• Appearance: /
• Density: 1.156 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: (S)-(-)-5 5-DIPHENYL-4-METHYL-2-OXAZOLI&(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-5 5-DIPHENYL-4-METHYL-2-OXAZOLI&(191090-29-6)
• EPA Substance Registry System: (S)-(-)-5 5-DIPHENYL-4-METHYL-2-OXAZOLI&(191090-29-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 191090-29-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-(-)-5,5-Diphenyl-4-methyl-2-oxazol is utilized as a key intermediate in organic synthesis for the development of complex organic molecules. Its oxazol ring allows for the formation of new carbon-carbon bonds, making it a valuable component in the synthesis of various compounds.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of asymmetric synthesis, (S)-(-)-5,5-Diphenyl-4-methyl-2-oxazol serves as a chiral auxiliary. This role is crucial for inducing specific stereochemistry during the synthesis process, leading to the production of enantiomerically pure compounds.
Used in Pharmaceutical Industry:
(S)-(-)-5,5-Diphenyl-4-methyl-2-oxazol finds applications in the pharmaceutical industry due to its ability to impart specific stereochemical properties to molecules. This feature is essential for the development of drugs with desired biological activities and selectivity.
Used in Agrochemicals:
(S)-(-)-5 5-DIPHENYL-4-METHYL-2-OXAZOLI& also has applications in agrochemicals, where its stereochemical properties can be leveraged to create molecules with targeted effects on pests or other agricultural concerns.
Used in Materials Science:
(S)-(-)-5,5-Diphenyl-4-methyl-2-oxazol is employed in materials science for the development of new materials with specific properties. (S)-(-)-5 5-DIPHENYL-4-METHYL-2-OXAZOLI&'s ability to influence stereochemistry can lead to the creation of materials with unique characteristics for various applications.

InChI:InChI=1/C16H15NO2/c1-12-16(19-15(18)17-12,13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-12H,1H3,(H,17,18)/t12-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 78603-91-5 (S)-2-amino-1,1-diphenylpropan-1-ol 
• 503-38-8 trichloromethyl chloroformate 
• 124-38-9 carbon dioxide 
• 98-59-9 p-toluenesulfonyl chloride 
• 42746-51-0 5,5-diphenyl-4-methyl-2-oxazolidinone 

Downstream Products

• 67659-37-4 (S)-1,1-diphenyl-2-aminopropane 
• 290351-99-4 (S)-2-Fluoro-1-methyl-2,2-diphenyl-ethylamine 

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).

Synthesis of chiral oxazolidin-2-ones by 1,2-amino alcohols, carbon dioxide and electrogenerated acetonitrile anion

An improved electrochemical synthesis of chiral oxazolidin-2-ones from chiral 1,2-amino alcohols is obtained by direct electrolysis of solutions of MeCN-TEAP containing the amino alcohol, with subsequent CO2 bubbling and addition of TsCl. This

A short synthesis of (S)-α-(diphenylmethyl)alkyl amines from amino acids

A range of (S)-α-(diphenylmethyl)alkyl amines were prepared from the corresponding (S)-α-amino acid ester hydrochlorides. These amines were derived by direct hydrogenation of their precursor oxazolidinones.

Synthesis of chiral oxazolidin-2-ones and imidazolidin-2-ones via DMAP- catalyzed isocyanation of amines with di-tert-butyl dicarbonate

Oxazolidin-2-ones and imidazolidin-2-ones are prepared under mild reaction conditions by DMAP-catalyzed isocyanation of 1,2-aminoalcohols and 1,2-diamines with di-tert-butyl dicarbonate and subsequent cyclization.