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

• ChemBase ID: 77291
• Molecular Formular: C6H11NS2
• Molecular Mass: 161.28824
• Monoisotopic Mass: 161.03329136
• SMILES: N1[C@H](C(C)C)CSC1=S
• Canonical SMILES: CC([C@@H]1CSC(=S)N1)C
• InChI: InChI=1S/C6H11NS2/c1-4(2)5-3-9-6(8)7-5/h4-5H,3H2,1-2H3,(H,7,8)/t5-/m0/s1
• InChIKey: CWIZUGZKLJDJLE-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-(propan-2-yl)-1,3-thiazolidine-2-thione
• IUPAC Traditional name: (4R)-4-isopropyl-1,3-thiazolidine-2-thione
• Synonyms: (4S)-4-(Prop-2-yl)-1,3-thiazolidine-2-thione; (4S)-4-Isopropyl-1,3-thiazolidine-2-thione; (R)-4-Isopropylthiazolidine-2-thione; (R)-4-Isopropylthiazolidine-2-thione; (R)-4-异丙基噻唑烷-2-硫酮

Database IDs

• CAS Number: 110199-16-1
• MDL Number: MFCD03844797; MFCD06658213
• PubChem SID: 162042164; 24845843
• PubChem CID: 13922954

CALCULATED PROPERTIES

• Acid pKa: 7.4438057
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 2.3256862
• LogD (pH = 7.4): 2.0929728
• Log P: 2.3300378
• Molar Refractivity: 46.9214 cm^3
• Polarizability: 18.727148 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 69-71 °C
• Optical Rotation: [α]20/D +37±3°, 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); 95+%
• Optical Purity: ee: ≥99:1 (LC)
• Empirical Formula (Hill Notation): C6H11NS2

DETAILS

Sigma Aldrich - 05329

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