Thiophene
Thiophene
Sgurr nan Gillean
<catset>Category="Heterocyclic compounds"</catset><catset>Category="Simple aromatic rings"</catset><right><p><table border=1 cellpadding=2 cellspacing=0 style="margin-left:1em"><tr><th colspan=2 align=center bgcolor=cccccc><b>Thiophene</b></th></tr><tr><td><a href="IUPAC nomenclature">Chemical name</a></td><td>Thiophene</td></tr><tr><td><a href="Chemical formula">Chemical formula</a></td><td>C<sub>4</sub>H<sub>4</sub>S</td></tr><tr><td><a href="Molecular mass">Molecular mass</a></td><td>84.14 g/mol</td></tr><tr><td><a href="Density">Density</a></td><td>1.051 g/ml</td></tr><tr><td><a href="Melting point">Melting point</a></td><td>-38.2 °C</td></tr><tr><td><a href="Boiling point">Boiling point</a></td><td>84.4 °C</td></tr><tr><td><a href="CAS registry number">CAS number</a></td><td>110-02-1</td></tr><tr><td><a href="Simplified molecular input line entry specification">SMILES</a></td><td>C1=CC=CS1</td></tr><tr><td colspan=2 align=center>[image]</td></tr></table><p></right><p><b>Thiophene</b> is a <a href="Heterocyclic compound">heterocyclic</a> <a href="Aromaticity">aromatic</a> <a href="Organic compound">Organic compound</a>. It is a clear colorless <a href="Lachrymatory agent">lachrymatory</a> liquid with a strong and very unpleasant odor. Thiophene is often found naturally occurring in <a href="Petroleum">Petroleum</a> in concentrations up to several percent. It is used as a denaturant in denatured ethylic alcohol.<p>Thiophene is aromatic because one of the two lone electron pairs of the <a href="Sulfur">Sulfur</a> atom contributes to the <a href="Delocalized electron">delocalized</a> <a href="Pi bond">pi electron</a> system, in a manner analogous to the compound <a href="Furan">Furan</a>. The aromaticity of thiophene is only slightly lower than that of <a href="Benzene">Benzene</a>.<h2 style="margin: 0; padding-top: 0.5em; padding-bottom: 0.17em; border-bottom: 1px solid #aaaaaa; font-size: 150%;">See also</h2><ul><li> <a href="Pyrrole">Pyrrole</a>, an analog with a <a href="Nitrogen">Nitrogen</a> atom instead of the <a href="Sulfur">Sulfur</a> <a href="Atom">Atom</a>. <li> <a href="Furan">Furan</a>, an analog with an <a href="Oxygen">Oxygen</a> instead of the sulfur atom. <li> <a href="Simple aromatic ring">Simple aromatic rings</a> </ul>