Ensiklopedia Dunia

Technopedia Center

Faculty of Engineering and Computer Science
S1 Informatics S1 Information Systems S1 Information Technology S1 Computer Engineering S1 Electrical Engineering S1 Civil Engineering

faculty of Economics and Business
S1 Management S1 Accountancy

Faculty of Letters and Educational Sciences
S1 English literature S1 English language education S1 Mathematics education S1 Sports Education

Benzofuran - Wikipedia

From Wikipedia, the free encyclopedia

Benzofuran

Names

Preferred IUPAC name

1-Benzofuran^[1]

Other names

Benzofuran^[1]
Coumarone
Benzo[b]furan

Identifiers

CAS Number

271-89-6^Y

3D model (JSmol)

Interactive image

Beilstein Reference

107704

ChEBI

CHEBI:35260^Y

ChEMBL

ChEMBL363614^Y

ChemSpider

8868^Y

DrugBank

DB04179^Y

ECHA InfoCard

100.005.439

EC Number

205-982-6

Gmelin Reference

260881

KEGG

C14512^Y

PubChem CID

9223

RTECS number

DF6423800

UNII

LK6946W774^Y

UN number

1993

CompTox Dashboard (EPA)

DTXSID6020141

InChI

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

SMILES

o2c1ccccc1cc2

Properties

C₈H₆O

118.135 g·mol⁻¹

−18 °C (0 °F; 255 K)

173 °C (343 °F; 446 K)

Hazards

GHS labelling:

Pictograms

Signal word

Warning

Hazard statements

H226, H351, H412

Precautionary statements

P201, P202, P210, P233, P240, P241, P242, P243, P273, P280, P281, P303+P361+P353, P308+P313, P370+P378, P403+P235, P405, P501

Lethal dose or concentration (LD, LC):

LD₅₀ (median dose)

500 mg/kg (mice).^[2]

Related compounds

Benzothiophene, Indole, Indene, 2-Cumaranone

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

verify (what is ^YN ?)

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 structural nucleus (parent compound) of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.

Production

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

Laboratory methods

Benzofurans can be prepared by various methods in the laboratory. Notable examples include:

O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration (cyclication) of the resulting ether and decarboxylation.^[3]

Perkin rearrangement, where a coumarin is reacted with a hydroxide:^[4]^[5]^[6]

Diels–Alder reaction^{[clarification needed]} of nitro vinyl furans with various dienophiles:^[7]

Cycloisomerization of alkyne ortho-substituted phenols:^[8]

Related compounds

Substituted benzofurans
Dibenzofuran, an analog with a second fused benzene ring.
Furan, an analog without the fused benzene ring.
Indole, an analog with a nitrogen instead of the oxygen atom.
Benzothiophene, an analog with a sulfur instead of the oxygen atom.
Isobenzofuran, the isomer with oxygen in the adjacent position.
Aurone
Thunberginol F

References

^ ^a ^b "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 218. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ ^a ^b Collin, G.; Höke, H. (2007). "Benzofurans". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.l03_l01. ISBN 978-3527306732.
^ Burgstahler, A. W.; Worden, L. R. (1966). "Coumarone" (PDF). Organic Syntheses. 46: 28; Collected Volumes, vol. 5, p. 251.
^ Perkin, W. H. (1870). "XXIX. On some New Bromine Derivatives of Coumarin". Journal of the Chemical Society. 23: 368–371. doi:10.1039/JS8702300368.
^ Perkin, W. H. (1871). "IV. On some New Derivatives of Coumarin". Journal of the Chemical Society. 24: 37–55. doi:10.1039/JS8712400037.
^ Bowden, K.; Battah, S. (1998). "Reactions of Carbonyl Compounds in Basic Solutions. Part 32. The Perkin Rearrangement". Journal of the Chemical Society, Perkin Transactions 2. 1998 (7): 1603–1606. doi:10.1039/a801538d.
^ Kusurkar, R. S.; Bhosale, D. K. (1990). "Novel Synthesis of Benzosubstituted Benzofurans Via Diels-Alder Reaction". Synthetic Communications. 20 (1): 101–109. doi:10.1080/00397919008054620.
^ Fürstner, Alois & Davies, Paul (2005). "Heterocycles by PtCl2-Catalyzed Intramolecular Carboalkoxylation or Carboamination of Alkynes". Journal of the American Chemical Society. 127 (43): 15024–15025. doi:10.1021/ja055659p. hdl:11858/00-001M-0000-0025-AA5A-1. PMID 16248631.

Simple aromatic rings

1 ring

Three-membered	Borirene Cyclopropenone
Five-membered	Furan Pyrrole Imidazole Thiophene Phosphole Pyrazole Oxazole Isoxazole Thiazole Isothiazole Triazole Tetrazole Pentazole
Six-membered	Benzene Pyridine Pyrazine Pyrimidine Pyridazine Triazine Tetrazine Pentazine Hexazine
Seven-membered	Borepin Tropone
Nine-membered	Azonine
18-membered	Cyclooctadecanonaene

2 rings

Five + Five	Diazapentalene Thienothiophene Trithiapentalene
Five + Six	Benzofuran Isobenzofuran Indole Isoindole Benzothiophene Benzo(c)thiophene Benzophosphole Benzimidazole Purine Indazole Benzoxazole Benzisoxazole Benzothiazole 5-Aza-7-deazapurine
Six + Six	Naphthalene Quinoline Isoquinoline Quinoxaline Quinazoline Cinnoline Phthalazine
Five + Seven	Azulene

Categories:

Hidden categories: