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298891 Sigma-Aldrich

(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone

99%

Synonym: (4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone

  • CAS Number 77943-39-6

  • Empirical Formula (Hill Notation) C10H11NO2

  • Molecular Weight 177.20

  •  Beilstein/REAXYS Number 1211705

  •  MDL number MFCD00010845

  •  PubChem Substance ID 24858003

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Auxiliaries, Oxazolidinone Derivatives
Quality Level   100
assay   99%
optical activity   [α]18/D +168°, c = 2 in chloroform
optical purity   ee: 98% (GLC)
mp   121-123 °C (lit.)
SMILES string   C[C@H]1NC(=O)O[C@H]1c2ccccc2
InChI   1S/C10H11NO2/c1-7-9(13-10(12)11-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H,11,12)/t7-,9-/m1/s1
InChI key   PPIBJOQGAJBQDF-VXNVDRBHSA-N

Description

Application

Evan′s chiral auxiliary (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone reacts with carboxylic acids to produce corresponding acyl derivatives in the presence of a diisopropylcarbodiimide reagent. It can also employed in the preparation of N-sulfinyloxazolidinone reagent (chiral sulfinyl transfer reagent), which reacts with nucleophiles such as Grignard reagents, enolates, and metalated amides to produce the chiral sulfoxides, sulfinate esters, and sulfonamides.

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

HPLC Analysis of 4-Methyl-5-Phenyl-2-Oxazolidone Enantiomers on Astec® CHIROBIOTIC® TAG

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of 4-Methyl-5-Phenyl-2-Oxazolidone Enantiomers on Astec® CHIROBIOTIC® TAG
Keywords: Chromatography, High performance liquid chromatography

Peer-Reviewed Papers
15

References

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