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

• ChemBase ID: 70464
• 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-/m0/s1
• InChIKey: QDMNNMIOWVJVLY-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-phenyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4R)-4-phenyl-1,3-oxazolidin-2-one
• Synonyms: (R)-4-Phenyloxazolidin-2-one; (R)-(-)-4-Phenyl-2-oxazolidinone; (R)-(-)-4-Phenyl-2-oxazolidinone; (4R)-4-Phenyl-1,3-oxazolidin-2-one; (R)-(-)-4-苯基-2-噁唑烷酮; (R)-(-)-4-苯基-2-恶唑琳酮

Database IDs

• CAS Number: 90319-52-1
• MDL Number: MFCD00192393
• Beilstein Number: 4308995
• PubChem SID: 162036180; 24865089
• PubChem CID: 730425

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

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 127-129°C; 129-132°C; 131-133 °C(lit.)
• Optical Rotation: [α]25/D -48°, c = 2 in chloroform; -55 (c=2 in chloroform)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT; N/A
• 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: 95+%; 98%
• Empirical Formula (Hill Notation): C9H9NO2

DETAILS

Sigma Aldrich - 402451

Packaging
1, 5 g in glass bottle
Application
Used for α-amino acid synthesis1 and the preparation of β-lactam antibiotics.2