4,5-dihydro-1,3-thiazole-2-thiol

• ChemBase ID: 123288
• Molecular Formular: C3H5NS2
• Molecular Mass: 119.2085
• Monoisotopic Mass: 118.98634117
• SMILES: C1(=NCCS1)S
• Canonical SMILES: SC1=NCCS1
• 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: 4,5-dihydro-1,3-thiazole-2-thiol
• IUPAC Traditional name: 2-mercaptothiazoline
• Synonyms: 4,5-dihydrothiazole-2-thiol; 2-Thiazolinethiol; 2-Mercaptothiazoline; 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: 162217641
• PubChem CID: 2723699

CALCULATED PROPERTIES

• H Donor: 1
• LogD (pH = 5.5): 1.3856876
• LogD (pH = 7.4): 0.6605873
• Log P: 1.3505415
• Molar Refractivity: 32.1648 cm^3
• Polarizability: 12.432495 Å^3
• Polar Surface Area: 12.36 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 6.4008007
• H Acceptors: 1

PROPERTIES

Physical Property

• Melting Point: 103-107°C

Safety Information

• RTECS: XJ6122000
• European Hazard Symbols: X
• UN Number: UN2811
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 22
• Safety Statements: 36
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Hazard statements: H301
• GHS Precautionary statements: P280F-P309-P310

Product Information

• Purity: 98+%

REFERENCES

• Used in the chain-lengthening of alkyl halides by trans-iodopropenylenation: Org. Synth. Coll., 6, 704 (1988):
  
• Reaction with ɑ-bromo esters gives the S-alkoxycarbonylmethyl derivatives, which can be C-alkylated by alkyl halides, using NaH as base. Sulfur-free products can be obtained by reduction (Zn/AcOH) to give the substituted acetic acid, or by reaction with iodidomethane to give the corresponding ɑ-iodo ester: Tetrahedron Lett., 2677 (1977).