From Wikipedia, the free encyclopedia Jump to: navigation, search Benzofuran IUPAC name[hide] 1-Benzofuran Other names[hide] Coumarone, benzo[b]furan Identifiers CAS number 271-89-6 Y PubChem 9223 ChemSpider 8868 Y KEGG C14512 Y ChEMBL CHEMBL363614 Y SMILES[show]
Boiling point 173 °C, 446 K, 343 °F
Y(what is this?) (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless solid is a component of coal tar. Benzofuran is the "parent" of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.
Contents[hide] [edit] Production Benzofuran is extracted from coal tar. It is also obtained by dehydrogenation of 2-ethylphenol.[1]
[edit] Laboratory methods Benzofuran can be prepared by O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration of the resulting ether.[2] In another method called the "Perkin rearrangement"[3][4] a coumarin is reacted with a hydroxide:
[edit] Related compounds
[edit] References
- o2c1ccccc1cc2
- InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H Y
Key: IANQTJSKSUMEQM-UHFFFAOYSA-N Y InChI=1/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
Key: IANQTJSKSUMEQM-UHFFFAOYAU
Boiling point 173 °C, 446 K, 343 °F
Y(what is this?) (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless solid is a component of coal tar. Benzofuran is the "parent" of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.
Contents[hide] [edit] Production Benzofuran is extracted from coal tar. It is also obtained by dehydrogenation of 2-ethylphenol.[1]
[edit] Laboratory methods Benzofuran can be prepared by O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration of the resulting ether.[2] In another method called the "Perkin rearrangement"[3][4] a coumarin is reacted with a hydroxide:
[edit] Related compounds
- Furan, an analog without the fused benzene ring.
- Indole, an analog with a nitrogen instead of the oxygen atom.
- Isobenzofuran, the isomer with oxygen in the adjacent position.
- Aurone
[edit] References
- ^ a b Gerd Collin, Hartmut Höke "Benzofurans" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi: 10.1002/14356007.l03_l01
- ^ Albert W. Burgstahler and Leonard R. Worden “Coumarone” Organic Syntheses, Collected Volume 5, p.251 (1973). http://www.orgsyn.org/orgsyn/pdfs/CV5P0251.pdf
- ^ W. H. Perkin, J. Chem. Soc., 1870, 23, 368; 1871, 24, 37.
- ^ Reactions of carbonyl compounds in basic solutions. Part 32.1 The Perkin rearrangement Keith Bowden and Sinan Battah J. Chem. Soc., Perkin Trans. 2, 1998, 1603 - 1606, doi:10.1039/a801538d
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