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216607

Sigma-Aldrich

Boron trifluoride diethyl etherate

purified by redistillation, ≥46.5% BF3 basis

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:
3909607
EC Number:
203-689-8
MDL number:
MFCD00013194
UNSPSC Code:
12352106
PubChem Substance ID:
57647937
NACRES:
NA.22

vapor density

4.9 (vs air)

vapor pressure

4.2 mmHg ( 20 °C)

form

liquid

purified by

redistillation

expl. lim.

36 %

concentration

≥46.5% boron trifluoride

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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Application

Catalyst in the synthesis of polyol chains. Reagent for the coupling of imines to allylstannanes and 4′-nitrobenzenesulfenanilide to alkenes and alkynes.

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

Signal Word

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The Journal of Organic Chemistry, 54, 4739-4739 (1989)
The Journal of Organic Chemistry, 54, 4982-4982 (1989)
Tetrahedron, 50, 12395-12395 (1994)
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)
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