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Merck

175501

Boron trifluoride diethyl etherate

synthesis grade, liquid

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
NACRES:
NA.22
PubChem Substance ID:
24850505
UNSPSC Code:
12352106
EC Number:
203-689-8
MDL number:
MFCD00013194
Beilstein/REAXYS Number:
3909607

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Product Name

Boron trifluoride diethyl etherate,

InChI key

MZTVMRUDEFSYGQ-UHFFFAOYSA-N

InChI

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

SMILES string

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

grade

synthesis grade

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.)

functional group

ether

storage temp.

2-8°C

Quality Level

200

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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

signalword

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

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
SHBT1700
SDBB3422
SHBS5621
SHBS5619
SDBB1791

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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)
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
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
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