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175501

Sigma-Aldrich

Boron trifluoride diethyl etherate

for synthesis

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

grade

for synthesis

Quality Level

vapor density

4.9 (vs air)

vapor pressure

4.2 mmHg ( 20 °C)

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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Related Categories

Packaging

5 mL in glass bottle
4×25, 100 mL in Sure/Seal™
4 L in glass bottle
1 L in Sure/Seal™
The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Application

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

Legal Information

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

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT RE 1 Inhalation

Target Organs

Kidney

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK Germany

WGK 1

Flash Point(F)

137.3 °F - closed cup

Flash Point(C)

58.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

European Journal of Organic Chemistry, 5378-5378 (2006)
Hui Xu et al.
Bioorganic & medicinal chemistry letters, 21(13), 4008-4012 (2011-06-03)
Twenty-one 4α-acyloxy-2-chloropodophyllotoxin derivatives (5a-u), whose C-4 spatial configuration was mainly stereocontrolled by the configuration of C-2 chlorine atom, were unexpectedly prepared by the reaction of 2-chloropodophyllotoxin with carboxylic acids in the presence of BF(3)·Et(2)O. Compared with ordinary esterifications of carboxylic...
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.
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....

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