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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:
111928
EC Number:
207-817-3
MDL number:
MFCD00005855
UNSPSC Code:
12352100
PubChem Substance ID:
24851085
NACRES:
NA.22

Quality Level

100

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

152.6 °F - closed cup

Flash Point(C)

67 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Catalytic hydrodeoxygenation of benzofuran and o-ethylphenol.
Lee C-L and Ollis DF.
J. Catal., 87(2), 325-331 (1984)
Guo-Hua Chu et al.
Bioorganic & medicinal chemistry letters, 15(23), 5114-5119 (2005-10-06)
Two novel chemical classes of kappa opioid receptor agonists, chroman-2-carboxamide derivatives and 2,3-dihydrobenzofuran-2-carboxamide derivatives, were synthesized. These agents exhibited high and selective affinity for the kappa opioid receptor.
Structures and stereochemical assignments of some novel chiral synthons derived from the biotransformation of 2, 3-dihydrobenzofuran and benzofuran by Pseudomonas putida.
Boyd DR, et al.
Tetrahedron Asymmetry, 4(6), 1307-1324 (1993)
Xiangtai Meng et al.
Organic letters, 11(1), 137-140 (2008-12-05)
A new bifunctional phosphine catalyst, (2'-hydroxy-biphenyl-2-yl)-diethylphosphane (LBBA-1), was developed for the highly stereoselective synthesis of cis-2,3-dihydrobenzofurans via an aza-Morita-Baylis-Hillman/umpolung addition domino reaction of salicyl N-thiophosphinyl imines with electron-deficient allenes. Dual activation of both nucleophile and electrophile by the bifunctional catalyst
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.
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