(4R)-4-(propan-2-yl)-1,3-oxazolidine-2-thione

• ChemBase ID: 77297
• Molecular Formular: C6H11NOS
• Molecular Mass: 145.22264
• Monoisotopic Mass: 145.05613498
• SMILES: N1[C@H](C(C)C)COC1=S
• Canonical SMILES: CC([C@@H]1COC(=S)N1)C
• InChI: InChI=1S/C6H11NOS/c1-4(2)5-3-8-6(9)7-5/h4-5H,3H2,1-2H3,(H,7,9)/t5-/m0/s1
• InChIKey: CIRDXQWBLPPFPN-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-(propan-2-yl)-1,3-oxazolidine-2-thione
• IUPAC Traditional name: (4R)-4-isopropyl-1,3-oxazolidine-2-thione
• Synonyms: (R)-4-Isopropyl-2-oxazolidinethione; (S)-4-Isopropyl-1,3-oxazolidine-2-thione; (R)-4-异丙基-2-噁唑烷硫酮

Database IDs

• CAS Number: 1217463-35-8
• MDL Number: MFCD06658218; MFCD00051949
• PubChem SID: 162042170; 24846234
• PubChem CID: 16211136

CALCULATED PROPERTIES

• Acid pKa: 8.698133
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 1.8348501
• LogD (pH = 7.4): 1.8162519
• Log P: 1.8350937
• Molar Refractivity: 40.4225 cm^3
• Polarizability: 16.331398 Å^3
• Polar Surface Area: 21.26 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 48-52 °C
• Optical Rotation: [α]/D +22±2°, c = 0.4 in chloroform

Safety Information

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

Product Information

• Purity: ≥95.0% (HPLC)
• Optical Purity: enantiomeric ratio: ≥99:1 (HPLC)
• Empirical Formula (Hill Notation): C6H11NOS

DETAILS

Sigma Aldrich - 08914

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