(4S,5R)-4-methyl-5-phenyl-1,3-oxazolidin-2-one

• ChemBase ID: 146427
• Molecular Formular: C10H11NO2
• Molecular Mass: 177.19984
• Monoisotopic Mass: 177.0789786
• SMILES: C[C@H]1[C@H](OC(=O)N1)c1ccccc1
• Canonical SMILES: C[C@@H]1NC(=O)O[C@@H]1c1ccccc1
• InChI: 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-/m0/s1
• InChIKey: PPIBJOQGAJBQDF-CBAPKCEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5R)-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S,5R)-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• Synonyms: (4S,5R)-(-)-4-Methyl-5-phenyl-2-oxazolidinone; (4S,5R)-4-Methyl-5-phenyloxazolidin-2-one; (4S,5R)-(-)-4-甲基-5-苯基-2-噁唑啉酮

Database IDs

• CAS Number: 16251-45-9
• MDL Number: MFCD00066226
• PubChem SID: 24860823; 162240623
• PubChem CID: 853161

CALCULATED PROPERTIES

• Acid pKa: 12.913281
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.8419691
• LogD (pH = 7.4): 1.8419679
• Log P: 1.8419691
• Molar Refractivity: 47.7188 cm^3
• Polarizability: 18.862381 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 121-123 °C(lit.)
• Optical Rotation: [α]25/D -168°, c = 2 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95+%; 99%
• Optical Purity: ee: 99% (HPLC)
• Empirical Formula (Hill Notation): C10H11NO2

DETAILS

Sigma Aldrich - 340529

Application
Versatile chiral auxiliary for asymmetric synthesis. For a review, see Aldrichimica Acta.1
Packaging
1, 5 g in glass bottle