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175501

Sigma-Aldrich

Boron trifluoride diethyl etherate

for synthesis

Synonym(s):

Boron trifluoride ethyl etherate

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About This Item

Linear Formula:
BF3 · O(C2H5)2
CAS Number:
109-63-7
Molecular Weight:
141.93
Beilstein/REAXYS Number:
3909607
EC Number:
203-689-8
MDL number:
MFCD00013194
UNSPSC Code:
12352106
PubChem Substance ID:
24850505
NACRES:
NA.22

grade

for synthesis

Quality Level

200

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

137.3 °F - closed cup

flash_point_c

58.5 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2236
SHBP0363
STBK3206
SHBN4461
SHBN3098

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European Journal of Organic Chemistry, 5378-5378 (2006)
Meng-Yang Chang et al.
Organic letters, 12(6), 1176-1179 (2010-03-03)
An easy and straightforward synthesis of 6,10b-diarylhexahydrobenzo[f]isoquinoline by the repeated treatment of boron trifluoride etherate (BF(3) x OEt(2)) is reported. The overall transformation from 4-arylpiperidin-3-one to benzo[f]isoquinoline proceeds via ring contraction, chain elongation, and intramolecular electrophilic cyclization in moderate yields.
(1-Alkynyl)dicarbonylcyclopentadienyliron complexes as electron-rich alkynes in organic synthesis: BF3-mediated [2+2] cycloaddition/ring-opening providing (2-alkenyl-1-imino)iron complexes.
Ryotaro Nakaya et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(31), 8559-8561 (2011-06-23)
Kevin M McQuaid et al.
Journal of the American Chemical Society, 131(2), 402-403 (2008-12-23)
C-H bond functionalization enables strategically new approaches to the synthesis of complex organic molecules including biologically active compounds, research probes and functional organic materials. To address the shortcomings of transition metal catalyzed processes, we have developed a new approach to
U C Reddy et al.
The Journal of organic chemistry, 74(6), 2605-2608 (2009-02-17)
A diastereoselective one-pot, three-component Prins-Friedel-Crafts reaction was developed for the synthesis of 4-aryltetrahydropyran derivatives from the reaction of carbonyl compounds with homoallylic alcohol in the presence of arene promoted by boron trifluoride etherate.
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