2,2'-Bithiophene

2,2'-Bithiophene is the organic compound. It is a colorless solid, although commercial samples are often greenish.[1] It is the most common of the three isomers with formula (C4H3S)2. The other two isomers have the connectivity 2,3'- and 3,3'-. The compound is typically prepared by cross-coupling starting from 2-halothiophenes.

2,2'-Bithiophene
Names
Other names
2,2'-bisthiophene, 2,2'-dithienyl, 2,2'-bithienyl, 2-(2-thienyl)thiophene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.062
EC Number
  • 207-767-2
Properties
C8H6S2
Molar mass 166.26 g·mol−1
Density 1.44 g/cm3
Melting point 33 °C (91 °F; 306 K)
Boiling point 260 °C (500 °F; 533 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

X-ray crystallography shows that the two rings are coplanar,[1] unlike the situation for biphenyl.

Occurrence

A number of bi- as well as terthiophenes exist naturally, invariably with substituents at the positions flanking sulfur. In terms of the biosynthesis, bithiophenes are proposed to be derived from polyacetylenic precursors, which in turn are the products of dehydrogenation of oleic acid. According to some hypotheses, these polyalkynes form labile 1,2-dithiins via a reaction with H2S2 or its equivalent.[2]

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References
  1. Chaloner, P. A.; Gunatunga, S. R.; Hitchcock, P. B. (1994). "Redetermination of 2,2'-bithiophene". Acta Crystallographica C. C50: 1941–2. doi:10.1107/S0108270194001149.
  2. Kagan, J. (1991). "Naturally occurring di- and trithiophenes". Progress in the Chemistry of Organic Natural Products. 56: 87–169..
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