(4R)-4-phenyl-1,3-oxazolidine-2-thione

• ChemBase ID: 77300
• Molecular Formular: C9H9NOS
• Molecular Mass: 179.23886
• Monoisotopic Mass: 179.04048491
• SMILES: N1C(=S)OC[C@H]1c1ccccc1
• Canonical SMILES: S=C1OC[C@H](N1)c1ccccc1
• InChI: InChI=1S/C9H9NOS/c12-9-10-8(6-11-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,12)/t8-/m0/s1
• InChIKey: LVIJIGQKFDZTNC-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-phenyl-1,3-oxazolidine-2-thione
• IUPAC Traditional name: (4R)-4-phenyl-1,3-oxazolidine-2-thione
• Synonyms: (4R)-4-Phenyl-2-thioxo-1,3-oxazolidine; (4R)-4-Phenyl-1,3-oxazolidine-2-thione; (R)-4-Phenyloxazolidine-2-thione; (R)-4-Phenyloxazolidine-2-thione; (R)-4-苯基噁唑烷-2-硫酮

Database IDs

• CAS Number: 171877-37-5
• MDL Number: MFCD06658220
• PubChem SID: 24844950; 162042173
• PubChem CID: 10845078

CALCULATED PROPERTIES

• Acid pKa: 8.587312
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 2.314949
• LogD (pH = 7.4): 2.2911336
• Log P: 2.3152637
• Molar Refractivity: 51.2909 cm^3
• Polarizability: 20.409678 Å^3
• Polar Surface Area: 21.26 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -75±5°, c = 0.2 in chloroform

Safety Information

• Storage Warning: Irritant/Air Sensitive/Store under Argon
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0%; 97%
• Optical Purity: enantiomeric ratio: 97.0:3.0 (LC)
• Empirical Formula (Hill Notation): C9H9NOS

DETAILS

Sigma Aldrich - 00762

Application
A highly selective and efficient chiral auxiliary1 which can be directly reduced to its corresponding aldehyde and the chiral auxiliary by reductive cleavage with diisobutylaluminum hydride.2
Evans-Type Oxazolidinethione And Thiazolidinethione Auxiliaries