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

• ChemBase ID: 77301
• Molecular Formular: C10H11NOS
• Molecular Mass: 193.26544
• Monoisotopic Mass: 193.05613498
• SMILES: N1[C@@H](COC1=S)Cc1ccccc1
• Canonical SMILES: S=C1OC[C@H](N1)Cc1ccccc1
• InChI: InChI=1S/C10H11NOS/c13-10-11-9(7-12-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,13)/t9-/m1/s1
• InChIKey: WJSUXYCBZFLXIK-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-benzyl-1,3-oxazolidine-2-thione
• IUPAC Traditional name: (4R)-4-benzyl-1,3-oxazolidine-2-thione
• Synonyms: (S)-4-Benzyl-1,3-oxazolidine-2-thione; (R)-4-Benzyloxazolidine-2-thione; (R)-4-Benzyloxazolidine-2-thione; (R)-4-苄基噁唑烷-2-硫酮

Database IDs

• CAS Number: 190970-58-2
• MDL Number: MFCD06658222; MFCD06658221
• PubChem SID: 162042174; 24844948
• PubChem CID: 5324406

CALCULATED PROPERTIES

• Acid pKa: 8.69626
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 2.6036801
• LogD (pH = 7.4): 2.5850039
• Log P: 2.603925
• Molar Refractivity: 56.0459 cm^3
• Polarizability: 22.257917 Å^3
• Polar Surface Area: 21.26 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 63-67 °C

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: ≥96.0% (HPLC); 97%
• Optical Purity: enantiomeric excess: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C10H11NOS

DETAILS

Sigma Aldrich - 00749

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