[(4S,5S)-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol

• ChemBase ID: 150717
• Molecular Formular: C11H13NO2
• Molecular Mass: 191.22642
• Monoisotopic Mass: 191.09462866
• SMILES: CC1=N[C@H]([C@@H](O1)c1ccccc1)CO
• Canonical SMILES: OC[C@@H]1N=C(O[C@H]1c1ccccc1)C
• InChI: InChI=1S/C11H13NO2/c1-8-12-10(7-13)11(14-8)9-5-3-2-4-6-9/h2-6,10-11,13H,7H2,1H3/t10-,11-/m0/s1
• InChIKey: NTCJMVHDZUBYNA-QWRGUYRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4S,5S)-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol
• IUPAC Traditional name: [(4S,5S)-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol
• Synonyms: (4S,5S)-(-)-4-Hydroxymethyl-2-methyl-5-phenyloxazoline; (4S,5S)-(-)-2-Methyl-5-phenyl-2-oxazoline-4-methanol; (4S,5S)-(-)-4-羟甲基-2-甲基-5-苯基噁唑啉; (4S,5S)-(-)-2-甲基-5-苯基-2-噁唑啉-4-甲醇

Database IDs

• CAS Number: 53732-41-5
• EC Number: 258-730-2
• MDL Number: MFCD00064825
• Beilstein Number: 1212843
• PubChem SID: 162244878; 24851283
• PubChem CID: 719469

CALCULATED PROPERTIES

• Acid pKa: 14.728958
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.1078016
• LogD (pH = 7.4): 1.1081945
• Log P: 1.1081996
• Molar Refractivity: 52.9118 cm^3
• Polarizability: 20.838717 Å^3
• Polar Surface Area: 41.82 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 61-65 °C(lit.); 63-67 °C
• Optical Rotation: [α]20/D -160±5°, c = 10.8% in chloroform; [α]20/D -172°, c = 10.8 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: ≥98.0% (sum of enantiomers, GC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C11H13NO2

DETAILS

Sigma Aldrich - 187666

Application
Reagent for the asymmetric reduction of ketones to secondary alcohols.
Packaging
1 g in glass bottle

Sigma Aldrich - 68701

Other Notes
Chiral auxiliary for the asymmetric addition of diethylzinc to aldehydes1