thiophene-2-thiol

• ChemBase ID: 87147
• Molecular Formular: C4H4S2
• Molecular Mass: 116.20456
• Monoisotopic Mass: 115.97544213
• SMILES: s1cccc1S
• Canonical SMILES: Sc1cccs1
• InChI: InChI=1S/C4H4S2/c5-4-2-1-3-6-4/h1-3,5H
• InChIKey: SWEDAZLCYJDAGW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: thiophene-2-thiol
• IUPAC Traditional name: thiophene-2-thiol
• Synonyms: 2-Mercaptothiophene; 2-Thiothiophene; 2-Sulphanylthiophene; Thiophene-2-thiol; Thienylmercaptan; 2-Thiophenethiol; 2-Thienyl mercaptan; Thiophene-2-thiol, contains dimer; 2-巯基噻吩; 噻吩-2-硫醇; 2-噻吩硫醇; 2-硫醇噻吩, 含二聚物

Database IDs

• CAS Number: 7774-74-5
• EC Number: 231-881-1
• MDL Number: MFCD00051666
• Beilstein Number: 104650
• PubChem SID: 24901457; 162074263
• PubChem CID: 522674
• FEMA ID: 3062
• Council of Europe Number: 478
• Flavis Number: 15.001

CALCULATED PROPERTIES

• Acid pKa: 5.8528934
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 1.8605711
• LogD (pH = 7.4): 0.81928843
• Log P: 2.0128908
• Molar Refractivity: 30.3335 cm^3
• Polarizability: 12.033643 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 129 °C(lit.); 62-65°C/2mm; 62-65°C/12mm
• Flash Point: 149 °F; 65 °C; 65.6°C
• Density: 1.230; 1.247; 1.252 g/mL at 25 °C(lit.)
• Refractive Index: 1.6170; n20/D 1.62(lit.)
• Hydrophobicity(logP): 2.281
• Organoleptic: caramel; coffee

Safety Information

• Storage Warning: Air & Light Sensitive; Harmful/Irritant/Stench/Air Sensitive/Light Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: X; Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 20/22-36/37/38; 36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H332-H315-H319-H335-H227; H315-H319-H335
• GHS Precautionary statements: P210-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Regulation Compliance: FDA 21 CFR (172.515)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: 95%; 97% as monomer
• Grade: Halal; Kosher
• Empirical Formula (Hill Notation): C4H4S2

DETAILS

Sigma Aldrich - W306207

Packaging
1 kg in glass bottle
1 sample in glass bottle
25, 100 g in glass bottle

REFERENCES

• The nature of the unusual reversible dimerization reaction which occurs on standing has been studied: J. Org. Chem., 54, 3224 (1989); Doklady Akad. Nauk., 305, 624 (1989):
  
• Reaction with 2-bromothiophene in the presence of a Cu catalyst and KOH in DMF gives 2,2'-dithienyl sulfide: Org. Synth. Coll., 6, 558 (1988); with 2-iodothiophene, the product is obtained in high yield in the absence of catalyst, base or solvent: Tetrahedron Lett., 36, 8439 (1995).
• Review of thiophenethiols: Russ. Chem. Rev., 60, 1309 (1991).