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Sigma-Aldrich

Boron trifluoride diethyl etherate

for synthesis

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Synonym(s):
Boron trifluoride ethyl etherate
Linear Formula:
BF3 · O(C2H5)2
CAS Number:
Molecular Weight:
141.93
Beilstein/REAXYS Number:
3909607
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22

grade

for synthesis

Quality Level

vapor density

4.9 (vs air)

vapor pressure

4.2 mmHg ( 20 °C)

form

liquid

expl. lim.

36 %

reaction suitability

core: boron
reagent type: Lewis acid
reagent type: catalyst

refractive index

n20/D 1.344 (lit.)

bp

126-129 °C (lit.)

mp

−58 °C (lit.)

density

1.15 g/mL (lit.)

storage temp.

2-8°C

SMILES string

CC[O+](CC)[B-](F)(F)F

InChI

1S/C4H10BF3O/c1-3-9(4-2)5(6,7)8/h3-4H2,1-2H3

InChI key

MZTVMRUDEFSYGQ-UHFFFAOYSA-N

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General description

Boron trifluoride diethyl etherate or boron trifluoride-ether complex is an organic compound widely used as a convenient source of boron trifluoride (BF3) in organic synthesis. It is also used as a Lewis acid for the activation of electrophiles.

Application

Catalyst used in the preparation of cyclopentyl- and cycloheptyl[b]indoles from aryl cyclopropyl ketones via [3+2] cycloaddition.
Lewis acid reagent with broad application

Packaging

The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

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Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT RE 1 Inhalation

target_organs

Kidney

wgk_germany

WGK 1

flash_point_f

closed cup

flash_point_c

closed cup

ppe

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


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European Journal of Organic Chemistry, 5378-5378 (2006)
Devendra J Vyas et al.
The Journal of organic chemistry, 75(19), 6720-6723 (2010-09-10)
The BF(3)·OEt(2)-mediated allylation of isatin with an α-chiral allylic stannane is diastereo- and enantioselective. Conversely, allylation of any substituted isatin employing the identical protocol is not diastereoselective at all and only enantioselective for the major diastereomer having syn relative configuration.
Yong-Gang Xiang et al.
Chemical communications (Cambridge, England), (45)(45), 7045-7047 (2009-11-12)
The synergistic action of BF(3).OEt(2) and SmI(2) allowed a series of intermolecular cross-couplings of readily available N-acyl N,O-acetals with alpha,beta-unsaturated compounds to be performed in high yields, which was applied to the stereoselective synthesis of pyrrolizidine alkaloid (+)-xenovenine.
Bjart Frode Lutnaes et al.
Journal of the American Chemical Society, 126(29), 8981-8990 (2004-07-22)
A series of charge-delocalized carotenoid mono- and dications have been prepared by treatment of selected carotenoids with Brønsted and Lewis acids. The detailed structures of the carbocations were established by NMR studies in the temperature range from -10 to -20
Brajendra K Sharma et al.
Journal of agricultural and food chemistry, 56(9), 3049-3056 (2008-04-11)
Vegetable oils are promising candidates as substitutes for petroleum base oils in lubricant applications, such as total loss lubrication, military applications, and outdoor activities. Although vegetable oils have some advantages, they also have poor oxidation and low temperature stability. One

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