Benzofuran

Benzofuran
Benzofuran
Identifiers
CAS number 271-89-6 YesY
PubChem 9223
ChemSpider 8868 YesY
UNII LK6946W774 YesY
DrugBank DB04179
KEGG C14512 YesY
ChEBI CHEBI:35260 YesY
ChEMBL CHEMBL363614 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H6O
Molar mass 118.13 g mol−1
Melting point

-18 °C, 255 K, -0 °F

Boiling point

173 °C, 446 K, 343 °F

Hazards
LD50 500 mg/kg (mice).[1]
 YesY (verify) (what is: YesY/N?)
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 liquid 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

Production

Benzofuran is extracted from coal tar. It is also obtained by dehydrogenation of 2-ethylphenol.[1]

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:

Perkin rearrangement

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
  • Thunberginol F

References

  1. ^ a b Gerd Collin, Hartmut Höke "Benzofurans" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi: 10.1002/14356007.l03_l01
  2. ^ Albert W. Burgstahler and Leonard R. Worden “Coumarone” Organic Syntheses, Collected Volume 5, p.251 (1973). http://www.orgsyn.org/orgsyn/pdfs/CV5P0251.pdf
  3. ^ W. H. Perkin, J. Chem. Soc., 1870, 23, 368; 1871, 24, 37.
  4. ^ 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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Look at other dictionaries:

  • Benzofuran — Strukturformel Allgemeines Name Benzofuran Andere Namen …   Deutsch Wikipedia

  • Benzofuran — Ben|zo|fu|ran, hier Benzo[b]furan [↑ Benzo (2), ↑ b (4) u. ↑ Furan] Syn.: (systematisch:) 1 Benzofuran, (veraltet:) Cumaron: eine fl. bicycl. Verb. aus einem Furanring mit ankondensiertem Benzolring, die zur Herst. von Copolymeren mit Inden… …   Universal-Lexikon

  • benzofuran — /ben zoh fyoor an, fyeuh ran /, n. Chem. coumarone. [1945 50; BENZO + FURAN] * * * …   Universalium

  • benzofuran — noun Any of a class of bicyclic heterocycles consisting of a benzene ring fused with one of furan. Syn: cumaron, coumarone …   Wiktionary

  • benzofuran — ben·zo·furan …   English syllables

  • benzofuran — ben•zo•fu•ran [[t]ˌbɛn zoʊˈfyʊər æn, fyəˈræn[/t]] n. chem. coumarone • Etymology: 1945–50 …   From formal English to slang

  • benzofuran — noun a colorless oily compound extracted from coal tar and used in manufacturing synthetic resins • Syn: ↑coumarone, ↑cumarone • Hypernyms: ↑compound, ↑chemical compound * * * “+ noun ( s) …   Useful english dictionary

  • (-)-1-(Benzofuran-2-yl)-2-propylaminopentane — Drugbox IUPAC name = (2 R ) 1 (1 Benzofuran 2 yl) N propylpentan 2 amine width= 200 CAS number= 260550 89 8 ATC prefix= ATC suffix= PubChem=9859674 DrugBank= C=16 | H=23 | N=1 | O=1 molecular weight = 245.37 bioavailability= metabolism =… …   Wikipedia

  • 2-Benzofuran-1,3-dion — Strukturformel Allgemeines Name Phthalsäureanhydrid Andere Namen …   Deutsch Wikipedia

  • 1-benzofuran — 1 benzfuranas statusas T sritis chemija apibrėžtis Heterociklinis junginys. formulė C₈H₆O atitikmenys: angl. coumarone; 1 benzofuran rus. кумарон; 1 бензофуран ryšiai: sinonimas – kumaronas …   Chemijos terminų aiškinamasis žodynas

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