2,2′-Bithiophene is the organic compound. It is a colorless solid, although commercial samples are often greenish.[3] 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.
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.[4]
Referencesedit
^ abPelletier, M.; Brisse, F. (1994). "Bithiophene at 133 K". Acta Crystallographica Section C Crystal Structure Communications. 50 (12): 1942–1945. doi:10.1107/S010827019301011X.
^ abChaloner, P. A.; Gunatunga, S. R.; Hitchcock, P. B. (1994). "Redetermination of 2,2′-bithiophene". Acta Crystallographica C. C50 (12): 1941–2. doi:10.1107/S0108270194001149.
^Kagan, J. (1991). "Naturally Occurring Di- and Trithiophenes. In: Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products". Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Vol. 56. pp. 87–169. doi:10.1007/978-3-7091-9084-5_2. ISBN978-3-7091-9086-9. PMID 2050313.
April 12, 2024
bithiophene, bithiophene, organic, compound, colorless, solid, although, commercial, samples, often, greenish, most, common, three, isomers, with, formula, c4h3s, other, isomers, have, connectivity, compound, typically, prepared, cross, coupling, starting, fro. 2 2 Bithiophene is the organic compound It is a colorless solid although commercial samples are often greenish 3 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 NamesPreferred IUPAC name 2 2 BithiopheneOther names 2 2 Bisthiophene 2 2 dithienyl 2 2 bithienyl 2 2 thienyl thiopheneIdentifiersCAS Number 492 97 73D model JSmol Interactive imageChemSpider 61428ECHA InfoCard 100 007 062EC Number 207 767 2PubChem CID 68120UNII 8CTS9HJ7L6 YCompTox Dashboard EPA DTXSID8060084InChI InChI 1S C8H6S2 c1 3 7 9 5 1 8 4 2 6 10 8 h1 6HKey OHZAHWOAMVVGEL UHFFFAOYSA NInChI 1 C8H6S2 c1 3 7 9 5 1 8 4 2 6 10 8 h1 6HKey OHZAHWOAMVVGEL UHFFFAOYABSMILES c1cc sc1 c2cccs2PropertiesChemical formula C 8H 6S 2Molar mass 166 26 g mol 1Appearance Colorless crystalsDensity 1 44 g cm3 1 Melting point 31 1 C 88 0 F 304 2 K 2 Boiling point 260 C 500 F 533 K 2 Structure 1 Crystal structure MonoclinicSpace group P21 cLattice constant a 7 873 A b 5 771 A c 8 813 Aa 90 b 107 07 g 90 Coordination geometry 2Except 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 3 unlike the situation for biphenyl Occurrence editA 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 4 References edit a b Pelletier M Brisse F 1994 Bithiophene at 133 K Acta Crystallographica Section C Crystal Structure Communications 50 12 1942 1945 doi 10 1107 S010827019301011X a b Haynes William M ed 2016 CRC Handbook of Chemistry and Physics 97th ed CRC Press p 3 58 ISBN 9781498754293 a b Chaloner P A Gunatunga S R Hitchcock P B 1994 Redetermination of 2 2 bithiophene Acta Crystallographica C C50 12 1941 2 doi 10 1107 S0108270194001149 Kagan J 1991 Naturally Occurring Di and Trithiophenes In Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products Vol 56 pp 87 169 doi 10 1007 978 3 7091 9084 5 2 ISBN 978 3 7091 9086 9 PMID 2050313 Retrieved from https en wikipedia org w index php title 2 2 27 Bithiophene amp oldid 1199623141, wikipedia, wiki, book, books, library,
