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183962

Sigma-Aldrich

2,3-Dihydrobenzofuran

99%

Synonym(s):

Coumaran

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About This Item

Empirical Formula (Hill Notation):
C8H8O
CAS Number:
496-16-2
Molecular Weight:
120.15
Beilstein/REAXYS Number:
111928
EC Number:
207-817-3
MDL number:
MFCD00005855
UNSPSC Code:
12352100
PubChem Substance ID:
24851085
NACRES:
NA.22

assay

99%

form

liquid

refractive index

n20/D 1.549 (lit.)

bp

188-189 °C (lit.)

solubility

alcohol: soluble
carbon disulfide: soluble
chloroform: soluble
diethyl ether: soluble

density

1.065 g/mL at 25 °C (lit.)

SMILES string

C1Cc2ccccc2O1

InChI

1S/C8H8O/c1-2-4-8-7(3-1)5-6-9-8/h1-4H,5-6H2

InChI key

HBEDSQVIWPRPAY-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544)

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General description

Biotransformation of 2,3-dihydrobenzofuran using intact cells of Pseudomonas putida UV4 has been investigated. 2,3-Dihydrobenzofuran is the intermediate formed during catalytic hydrodeoxygenation of benzofuran.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

152.6 °F - closed cup

flash_point_c

67 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
STBF0877V
07220CJ
S47192
13318BJ
06503AH

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2,3-Dihydrofuran

Prashant P Deshpande et al.
Journal of industrial microbiology & biotechnology, 35(8), 901-906 (2008-05-23)
Microbial hydroxylation of o-bromophenylacetic acid provided 2-bromo-5-hydroxyphenylacetic acid. This enabled a route to the key intermediate 4-bromo-2,3-dihydrobenzofuran for synthesizing a melatonin receptor agonist and sodium hydrogen exchange compounds. Pd-mediated coupling reactions of 4-bromo-2,3-dihydrobenzofuran provided easy access to the 4-substituted-2,3-dihydrobenzofurans.
Łukasz Albrecht et al.
Angewandte Chemie (International ed. in English), 50(52), 12496-12500 (2011-11-09)
Fine-tuning: Three types of optically active trans-2,3-disubstituted-2,3-dihydrobenzofurans having three contiguous stereogenic centers can be efficiently accessed by one-pot reaction cascades (see scheme; TMS = trimethylsilyl). High substitution diversity of the final products can be achieved from the same common precursors
Derrick L J Clive et al.
Chemical communications (Cambridge, England), (21)(21), 2151-2153 (2007-05-24)
(-)-Conocarpan (1) was synthesized by a method based on radical cyclization, and the absolute configuration was established by chemical degradation; the original 2R,3R-assignment to (+)-conocarpan should be reversed, as suggested by a later chiroptical study of model 2,3-dihydrobenzofurans.
Leticia Jiménez-González et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 12(34), 8762-8769 (2006-09-06)
2,3-Dihydrobenzofurans can be diastereoselectively prepared by condensation of aromatic aldehydes with 2,3-dihydrobenzoxasilepines under the catalysis of Ag(I) complexes, and in the presence of a source of fluoride ion. The application of this strategy by using chiral catalysts leads to a
H S Heine et al.
Chemico-biological interactions, 59(2), 219-230 (1986-09-01)
The effects of dietary administration of equimolar doses (5 mmol/kg body wt per day) of trimethylene oxide, trimethylene sulfide, coumaran, benzofuran, indole, and indole-3-carbinol on the activities of microsomal epoxide hydrolase and several other xenobiotic metabolizing enzymes were measured in
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