(4S)-4-phenyl-1,3-thiazolidine-2-thione

• ChemBase ID: 77293
• Molecular Formular: C9H9NS2
• Molecular Mass: 195.30446
• Monoisotopic Mass: 195.01764129
• SMILES: N1[C@@H](c2ccccc2)CSC1=S
• Canonical SMILES: S=C1SC[C@@H](N1)c1ccccc1
• InChI: InChI=1S/C9H9NS2/c11-9-10-8(6-12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,11)/t8-/m1/s1
• InChIKey: IEXSISKCCADMLK-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-phenyl-1,3-thiazolidine-2-thione
• IUPAC Traditional name: (4S)-4-phenyl-1,3-thiazolidine-2-thione
• Synonyms: (S)-4-Phenylthiazolidine-2-thione; (S)-4-Phenyl-1,3-thiazolidine-2-thione; (S)-4-Phenylthiazolidine-2-thione; (S)-4-苯基噻唑啉-2-硫酮

Database IDs

• CAS Number: 185137-29-5
• MDL Number: MFCD06658214
• PubChem SID: 24864789; 162042166
• PubChem CID: 11333042

CALCULATED PROPERTIES

• Acid pKa: 7.3330674
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 2.8046024
• LogD (pH = 7.4): 2.5286694
• Log P: 2.8102078
• Molar Refractivity: 57.7898 cm^3
• Polarizability: 22.816227 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +207±5°, c = 1% 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: ≥98.0% (GC); 97%
• Optical Purity: enantiomeric ratio: ≥99:1 (LC)
• Empirical Formula (Hill Notation): C9H9NS2

DETAILS

Sigma Aldrich - 39911

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