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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)

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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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

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

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

European Journal of Organic Chemistry, 5378-5378 (2006)
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
Pipas Saha et al.
Organic & biomolecular chemistry, 9(12), 4626-4634 (2011-04-23)
An efficient methodology for the synthesis of oxabicyclo[3.3.1]nonenes and substituted tetrahydropyrans has been developed in moderate yields from the reaction of geraniol with aldehydes and epoxides promoted by boron trifluoride etherate.
Kiyoshi Ikeda et al.
Bioorganic & medicinal chemistry, 11(14), 3073-3076 (2003-06-24)
A combined system of bismuth triflate [Bi(OTf)(3)] and boron trifluoride etherate (BF(3).OEt(2)) in dichloromethane is an efficient promoter for the glycosylation of N-acetylneuraminic acid derivatives. The co-existence of two acid catalysts such as Bi(OTf)(3)-BF(3).OEt(2) or Bi(OTf)(3)-PPA is confirmed to be
Tito Akindele et al.
Chemical & pharmaceutical bulletin, 58(2), 265-269 (2010-02-02)
Enantiomerically enriched sulfonamides were synthesized by the radical addition of an acetal to enantiomerically pure N-sulfinyl imines using dimethylzinc-air and boron trifluoride diethyl etherate. Higher levels of stereocontrol were observed by using a mesitylenesulfinyl group. Furthermore, an amine and an

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