(4R)-5,5-dimethyl-4-(propan-2-yl)-1,3-oxazolidin-2-one

• ChemBase ID: 145952
• Molecular Formular: C8H15NO2
• Molecular Mass: 157.2102
• Monoisotopic Mass: 157.11027873
• SMILES: CC(C)[C@@H]1C(OC(=O)N1)(C)C
• Canonical SMILES: CC([C@H]1NC(=O)OC1(C)C)C
• InChI: InChI=1S/C8H15NO2/c1-5(2)6-8(3,4)11-7(10)9-6/h5-6H,1-4H3,(H,9,10)/t6-/m1/s1
• InChIKey: QICFUFOXXNIZFF-ZCFIWIBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-5,5-dimethyl-4-(propan-2-yl)-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4R)-4-isopropyl-5,5-dimethyl-1,3-oxazolidin-2-one
• Synonyms: (R)-(+)-4-Isopropyl-5,5-dimethyl-2-oxazolidinone; (R)-(+)-4-异丙基-5,5-二甲基-2-噁唑烷酮

Database IDs

• CAS Number: 223906-38-5
• MDL Number: MFCD01321230
• PubChem SID: 162240152; 24868257
• PubChem CID: 10583042

CALCULATED PROPERTIES

• Acid pKa: 13.216943
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.6423758
• LogD (pH = 7.4): 1.6423752
• Log P: 1.6423758
• Molar Refractivity: 41.4886 cm^3
• Polarizability: 16.65312 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 86-87 °C(lit.)
• Flash Point: 20 °C; 68 °F
• Optical Rotation: [α]20/D +47°, c = 1 in H2O

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 11-36/37/38
• Safety Statements: 16-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C8H15NO2

DETAILS

Sigma Aldrich - 450669

Application
Versatile chiral auxiliary for asymmetric synthesis used in diastereoselective Michael additions.1
Packaging
250 mg in glass bottle