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655228

Sigma-Aldrich

Potassium vinyltrifluoroborate

95%

Synonym(s):

Potassium (ethenyl)trifluoroborate

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About This Item

Linear Formula:
CH2=CHBF3K
CAS Number:
13682-77-4
Molecular Weight:
133.95
MDL number:
MFCD02093335
UNSPSC Code:
12352103
PubChem Substance ID:
24884089
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

Assay

95%

form

solid

SMILES string

[K+].F[B-](F)(F)C=C

InChI

1S/C2H3BF3.K/c1-2-3(4,5)6;/h2H,1H2;/q-1;+1

InChI key

ZCUMGICZWDOJEM-UHFFFAOYSA-N

General description

Potassium vinyltrifluoroborate is a versatile organometallic reagent used as a vinylating agent in the presence of palladium catalysts.[1]

Potassium vinyltrifluoroborate is an air- and water-stable potassium organotrifluoroborate that can be utilized in coupling reactions under relatively mild conditions.[2][3][4][5]

Application

Organotrifluoroborate involved in:
  • Suzuki Miyaura cross-coupling reactions and polymerization reactions
  • Synthesis of photonic crystals
  • Synthesis of sensitizers for dye-sensitized solar cells
  • Mannich / diastereoselective hydroamination reaction sequence

Organotrifluoroborates as versatile and stable boronic acid surrogates.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN1388
SHBL4557
SHBK3923
SHBH9664
SHBG2993V

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Sigma-Aldrich

750271

Potassium trans-1-propenyltrifluoroborate

New poly (phenylenevinylene)-methyl methacrylate-based photonic crystals.
Achelle S, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 48(12), 2659-2665 (2010)
Suzuki- Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles.
Molander GA and Brown AR
The Journal of Organic Chemistry, 71(26), 9681-9686 (2006)
Potassium Ethenyl Trifluoroborate
Molander GA and Cooper DJ
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
The suzuki-heck polymerization as a tool for the straightforward obtainment of poly (fluorenylene-vinylene) sensitizers for dye-sensitized solar cells.
Grisorio R, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 49(4), 842-847 (2011)
Xuejuan Ma et al.
Journal of hazardous materials, 355, 65-73 (2018-05-19)
The degradation of organophosphorous nerve agents is of primary concern due to the severe toxicity of these agents. Based on the active center of organophosphorus hydrolase (OPH), a bimetallic nuclear ligand, (5-vinyl-1,3-phenylene)bis(di(1H-imidazol-2-yl) methanol) (VPIM), was designed and synthesized, which contains
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Potassium Trifluoroborate Salts

Potassium trifluoroborates are moisture- and air-stable organoboron reagents suitable for oxidative conditions.

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