2-(thiophen-2-yl)thiophene

• ChemBase ID: 8514
• Molecular Formular: C8H6S2
• Molecular Mass: 166.26324
• Monoisotopic Mass: 165.99109219
• SMILES: c1cc(sc1)c1sccc1
• Canonical SMILES: c1csc(c1)c1cccs1
• InChI: InChI=1S/C8H6S2/c1-3-7(9-5-1)8-4-2-6-10-8/h1-6H
• InChIKey: OHZAHWOAMVVGEL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(thiophen-2-yl)thiophene
• IUPAC Traditional name: 2,2'-bithiophene
• Synonyms: 2,2′-Bithienyl; 2,2′-Dithienyl; 2,2′-Bithiophene; 2,2-Bithiophene; 2,2'-Bithiophene; 2,2'-Bithienyl; 2,2'-Dithienyl; 2,2'-Bithiophene; 2,2'-二噻吩; 2,2'-联噻吩; 联二噻吩; 2,2'-二噻吩

Database IDs

• CAS Number: 492-97-7
• EC Number: 207-767-2
• MDL Number: MFCD00005414
• Beilstein Number: 3039
• PubChem SID: 24854316; 160971821; 24849247
• PubChem CID: 68120

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.1747673
• LogD (pH = 7.4): 3.1747673
• Log P: 3.1747673
• Molar Refractivity: 44.974 cm^3
• Polarizability: 18.601217 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 30-33°C; 32-33 °C(lit.); 32-33°C; 32-34 °C
• Boiling Point: 260 °C(lit.); 260°C; 260°C
• Flash Point: >110°C(230°F); 110 °C; 110°C; 230 °F

Safety Information

• Storage Warning: IRRITANT; Irritant; Light Sensitive
• German water hazard class: 3
• TSCA Listed: true; 是
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: ≥97.0% (GC); 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C8H6S2

DETAILS

Sigma Aldrich - 241636

Application
Substrate used in a rhodium-catalyzed C-H arylation of heteroarenes with aryl iodides.1
Packaging
10 g in glass bottle

REFERENCES

• Can be converted to its 5-lithio- and 5,5'-dilithio derivatives by PhLi and n-BuLi respectively. Chemistry of this type has found applications in synthesis of: liquid crystal molecules: Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A, 218, 113 (1992); bithienoquinoid compounds as electron donors for organic conductors: Tetrahedron Lett., 33, 5405 (1992); conjugated thiophene oligomers as organic semiconductors: J. Am. Chem. Soc., 115, 8716 (1993); polythiophenes as conducting polymers: Synth. Met., 55, 420 (1993).