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

• ChemBase ID: 70023
• Molecular Formular: C9H9NO2
• Molecular Mass: 163.17326
• Monoisotopic Mass: 163.06332853
• SMILES: O1C(=O)N[C@H](C1)c1ccccc1
• Canonical SMILES: O=C1OC[C@@H](N1)c1ccccc1
• InChI: InChI=1S/C9H9NO2/c11-9-10-8(6-12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,11)/t8-/m1/s1
• InChIKey: QDMNNMIOWVJVLY-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-phenyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S)-4-phenyl-1,3-oxazolidin-2-one
• Synonyms: (S)-(+)-4-Phenyl-2-oxazolidinone; (S)-(+)-4-Phenyl-2-oxazolidinone; (4S)-(+)-4-Phenyl-1,3-oxazolidin-2-one; (S)-4-Phenyloxazolidin-2-one; (S)-(+)-4-苯基-2-噁唑烷酮; (S)-(+)-4-苯基-2-恶烷唑

Database IDs

• CAS Number: 99395-88-7
• MDL Number: MFCD00043396
• Beilstein Number: 131918
• PubChem SID: 162035748; 24863459; 24887377
• PubChem CID: 730424

CALCULATED PROPERTIES

• Acid pKa: 12.515766
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.425394
• LogD (pH = 7.4): 1.4253912
• Log P: 1.425394
• Molar Refractivity: 43.3 cm^3
• Polarizability: 17.026276 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 129-132 °C; 129-132 °C(lit.); 129-132°C; 130-132°C
• Optical Rotation: [α]20/D +48°, c = 2 in chloroform; [α]20/D +49±2°, c = 2% in chloroform stab. with amylenes; +52 (c=2 in chloroform)

Safety Information

• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 95+%; 98%
• Grade: puriss.
• Empirical Formula (Hill Notation): C9H9NO2

DETAILS

Sigma Aldrich - 376698

Application
Versatile chiral auxiliary for asymmetric synthesis which is easily recycled under mild conditions, thus enhancing its commercial potential. For a recent review, see Aldrichimica Acta .1
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 78875

Other Notes
Chiral auxiliary used for the enantioselective synthesis of β-lactams1,2,3,4; Used as recyclable derivatizing agent for the chromatographic resolution of primary amines via allophanates5