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Key Documents

209929

Sigma-Aldrich

2-Ethoxytetrahydrofuran

99%

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About This Item

Empirical Formula (Hill Notation):
C6H12O2
CAS Number:
Molecular Weight:
116.16
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

assay

99%

form

liquid

refractive index

n20/D 1.414 (lit.)

bp

170-172 °C (lit.)

density

0.908 g/mL at 25 °C (lit.)

SMILES string

CCOC1CCCO1

InChI

1S/C6H12O2/c1-2-7-6-4-3-5-8-6/h6H,2-5H2,1H3

InChI key

JQYYUWHWGCJWTN-UHFFFAOYSA-N

General description

2-Ethoxytetrahydrofuran undergoes Ln(OTf)3-catalyzed-Povarov coupling reaction with anilines and cyclopentadiene to yield tetrahydroquinolines. Transacetalization of 2-ethoxytetrahydrofuran with various alcohols catalyzed by Fe(ClO4)3 has been reported.

Application

2-Ethoxytetrahydrofuran was used to investigate quantitative, regioselective, O-acylative cleavage of tetrahydrofurans using organic acid halides in the presence of Bi(III) halides.

pictograms

Flame

signalword

Danger

hcodes

Hazard Classifications

Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

60.8 °F - closed cup

flash_point_c

16 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Bi (III) halides as efficient catalysts for the O-acylative cleavage of tetrahydrofurans: an expeditious entry to tetralins.
Coles SJ, et al.
Tetrahedron, 61(18), 4447-4452 (2005)
Lanthanide (III)-catalyzed multi-component aza-Diels-Alder reaction of aliphatic N-arylaldimines with cyclopentadiene.
Powell DA and Batey RA.
Tetrahedron Letters, 44(41), 7569-7573 (2003)
Fe3+-Catalyzed transacetalization of 2-alkoxytetrahydrofurans with alcohols.
Yamanaka D, et al.
Tetrahedron Letters, 49(1), 53-56 (2008)

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