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

• ChemBase ID: 77295
• Molecular Formular: C10H11NS2
• Molecular Mass: 209.33104
• Monoisotopic Mass: 209.03329136
• SMILES: N1[C@@H](Cc2ccccc2)CSC1=S
• Canonical SMILES: S=C1SC[C@@H](N1)Cc1ccccc1
• InChI: InChI=1S/C10H11NS2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m0/s1
• InChIKey: SLDUGQISGRPGAW-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-benzyl-1,3-thiazolidine-2-thione
• IUPAC Traditional name: (4S)-4-benzyl-1,3-thiazolidine-2-thione
• Synonyms: (S)-4-Benzyl-1,3-thiazolidine-2-thione; (S)-4-Benzylthiazolidine-2-thione; (S)-4-Benzylthiazolidine-2-thione; (S)-4-苄基噻唑啉-2-硫酮

Database IDs

• CAS Number: 171877-39-7
• MDL Number: MFCD06658216
• PubChem SID: 162042168; 24845912
• PubChem CID: 11458470

CALCULATED PROPERTIES

• Acid pKa: 7.441936
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 3.0944986
• LogD (pH = 7.4): 2.8610902
• Log P: 3.098869
• Molar Refractivity: 62.5448 cm^3
• Polarizability: 24.66528 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -122±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: ≥97.0% (GC); 95+%
• Optical Purity: enantiomeric ratio: ≥99:1 (LC)
• Empirical Formula (Hill Notation): C10H11NS2

DETAILS

Sigma Aldrich - 06357

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