1,3-thiazolidine-2-thione

• ChemBase ID: 146562
• Molecular Formular: C3H5NS2
• Molecular Mass: 119.2085
• Monoisotopic Mass: 118.98634117
• SMILES: C1CSC(=S)N1
• Canonical SMILES: S=C1NCCS1
• InChI: InChI=1S/C3H5NS2/c5-3-4-1-2-6-3/h1-2H2,(H,4,5)
• InChIKey: WGJCBBASTRWVJL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-thiazolidine-2-thione
• IUPAC Traditional name: 2-mercaptothiazoline
• Synonyms: 2-Mercapto-2-thiazoline; 2-Thiazoline-2-thiol; Thyroidan; WR 305; 2-Mercaptothiazoline; 2-Thiazolidinethione; 1,3-Thiazolidine-2-thione; 2-Mercapto-4,5-dihydrothiazole; 2-Thiazoline-2-thiol; 2-Thiothiazolidone; 4,5-Dihydro-2-mercaptothiazole; 4,5-Dihydrothiazole-2-thiol; Metabasal; NSC 680; Sancelent 2MT; Tetrahydrothiazole-2-thione; 2-巯基-2-噻唑啉; 2-巯基噻唑啉

Database IDs

• CAS Number: 96-53-7
• EC Number: 202-512-1
• MDL Number: MFCD00126013
• Beilstein Number: 106332
• PubChem SID: 24897083; 162240756; 24882953
• PubChem CID: 2723699

CALCULATED PROPERTIES

• Acid pKa: 7.5571294
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 1.0226105
• LogD (pH = 7.4): 0.8296247
• Log P: 1.0259676
• Molar Refractivity: 33.507 cm^3
• Polarizability: 13.19219 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 100-105 °C; 100-105 °C(lit.); 95-99°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: XJ6122000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥97.0% (T); 98%
• Grade: technical
• Empirical Formula (Hill Notation): C3H5NS2

DETAILS

Sigma Aldrich - M6204

Packaging
100, 500 g in poly bottle
Application
Tool for highly selective chiral syntheses of penam- and carbapenam-type β-lactam antibiotics.1,2

Sigma Aldrich - 63860

Other Notes
Reagent for the iodomethylation of alkyl halides1; Educt for the preparation of active derivatives of carboxylic acids; these may be reduced to the aldehydes2,3; or aminolyzed to amides, e.g. chemoselective acylation of amino acids, e.g. selective prepn. of Ndelta-Z-lysine from lysine4

Toronto Research Chemicals - M225550

2-Mercaptothiazoline is an antithyroid agent that strongly reduces thyroid hormone levels. 2-Mercaptothiazoline is also used as an intermediate in the preparation of pesticides and other biologically active compounds.

REFERENCES

• Thomes, J. et al.: Jap. J. Pharmacol., 58, 201 (1992)
• Buxeraud, J. et al.: Eur. J. Med. Chem., 20, 43 (1992)
• Cheng, J. et al.: Nongyao, 38, 12 (1992)