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thiophene
Sign in to saveAlso known as Thiophen, thiofuran, Thiotetrole, Divinylene sulfide, Thio-Furan, Thiaphene, Thiole, Thiofurfuran
Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reactions, it resembles benzene. Compounds analogous to thiophene include furan (C4H4O), selenophene (C4H4Se) and pyrrole (C4H4NH), which each vary by the heteroatom in the ring.
Chemical data
- Formula
- C4H4S
- Molecular weight
- 84.14 g/mol
- IUPAC name
- thiophene
- SMILES
- C1=CSC=C1
- InChIKey
- YTPLMLYBLZKORZ-UHFFFAOYSA-N
- XLogP
- 1.8
- Polar surface area
- 28.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 84.003
Show 8 more facts
- Commons category
- Thiophene
- chemical formula
- C₄H₄S
- canonical SMILES
- C1=CSC=C1
- MCN code
- 2934.99.41
- melting point
- -39.4
- boiling point
- 84.0
- ionization energy
- 8.87
- electric dipole moment
- 0.55
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Article
16 sectionsContents
- Isolation and occurrence
- On Mars
- Synthesis and production
- Properties and structure
- Reactivity
- Oxidation
- Alkylation
- Desulfurization
- Polymerization
- Coordination chemistry
- Thiophene derivatives
- Thienyl
- Ring-fused thiophenes
- Uses
- References
- External links
Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reactions, it resembles benzene. Compounds analogous to thiophene include furan (C4H4O), selenophene (C4H4Se) and pyrrole (C4H4NH), which each vary by the heteroatom in the ring.
==Isolation and occurrence== Thiophene was discovered by Viktor Meyer in 1882 as a contaminant in benzene. It was observed that isatin (an indole) forms a blue dye if it is mixed with sulfuric acid and crude benzene. The formation of the blue indophenin had long been believed to be a reaction of benzene itself. Viktor Meyer was able to isolate thiophene as the actual substance responsible for this reaction.