3-hydroxy-4-methyl-2,3-dihydro-1,3-thiazole-2-thione

• ChemBase ID: 75081
• Molecular Formular: C4H5NOS2
• Molecular Mass: 147.2186
• Monoisotopic Mass: 146.98125579
• SMILES: s1c(=S)n(c(c1)C)O
• Canonical SMILES: Cc1csc(=S)n1O
• InChI: InChI=1S/C4H5NOS2/c1-3-2-8-4(7)5(3)6/h2,6H,1H3
• InChIKey: LOKDIDVKVVVVHK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-hydroxy-4-methyl-2,3-dihydro-1,3-thiazole-2-thione
• IUPAC Traditional name: 3-hydroxy-4-methyl-1,3-thiazole-2-thione
• Synonyms: 2-Mercapto-4-methylthiazole N-oxide; 3-Hydroxy-4-methyl-1,3-thiazole-2(3H)-thione; 2-Mercapto-4-methylthiazole 3-oxide; 3-Hydroxy-4-methyl-2(3H)-thiazolethione; 2-巯-4-甲基噻唑 3-氧化物; 3-羟基-4-甲基-2(3H)-噻唑硫酮

Database IDs

• CAS Number: 49762-08-5
• MDL Number: MFCD00077793
• Beilstein Number: 1210145
• PubChem SID: 24862354; 162039999
• PubChem CID: 341593

CALCULATED PROPERTIES

• Acid pKa: 7.254169
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.4472195
• LogD (pH = 7.4): 1.0772785
• Log P: 1.45477
• Molar Refractivity: 40.5061 cm^3
• Polarizability: 15.425732 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 92-94 °C; 92-94 °C(lit.); 92-94°C

Safety Information

• Storage Warning: Harmful/Irritant/Light Sensitive/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (UV); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C4H5NOS2

DETAILS

Sigma Aldrich - 363197

Packaging
1 g in glass bottle
Application
Useful in the Barton reaction for the generation of carbon radicals through decarboxylative rearrangement of the corresponding esters.1

Sigma Aldrich - 55873

Other Notes
Esters of carboxylic acids with this thiazolethione undergo smooth radical decarboxylation to alkyl radicals which can be trapped in a synthetically useful manner1,2,3,4