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655228 Sigma-Aldrich

Potassium vinyltrifluoroborate

95%

Synonym: Potassium (ethenyl)trifluoroborate

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Properties

Related Categories Alkenyl Trifluoroborate Salts, Boronic Acids and Derivatives, Chemical Synthesis, Organometallic Reagents, Trifluoroborate Salts More...
Quality Level   100
assay   95%
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

Description

General description

Potassium vinyltrifluoroborate is an air- and water-stable potassium organotrifluoroborate that can be utilized in coupling reactions under relatively mild conditions.

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.

Packaging

1, 5, 25, 100 g in poly bottle

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3261 8 / PGII
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

New Trifl uoroborate Salts for Suzuki Coupling from Aldrich R&D

Trifluoroborates are air-stable alternatives to boronic acids in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions.1,2 They are more robust, easier to handle, and less prone to protodeboron...
Aldrich ChemFiles 2005, 5.5, 11.
Keywords: Catalysis, Chemfiles, Coupling reactions, Cross couplings

Potassium Trifluoroborate Salts

Boronic acids, boronate esters, and organoboranes have been utilized for many years as the primary boron source in Suzuki–Miyaura-type reactions. These organoboron reagents have inherent limitations ...
ChemFiles Volume 5 Article 10
Keywords: Aldrichimica Acta, Coupling reactions, Cross couplings, Degradations, Epoxidations, Type

Potassium Vinyltrifluoroborate as a Versatile Dianion Precursor

Molander and co-workers have developed a powerful strategy for the production of a unique 1,2-dianion equivalent using potassium vinyltrifluoroborate.1 This useful organotrifluoroborate undergoes sel...
Aaron Thornton
Chemfiles Volume 11 Article 1
Keywords: Cross couplings

Professor and Product Portal - Gary Molander Group

From our library of Articles, Sigma-Aldrich presents Professor and Product Portal - Gary Molander Group
Keywords: Catalysis, Coupling reactions, Cross couplings, Transmetalation

Related Content

Organotrifluoroborates in Chemical Synthesis

Potent Boronic Acid Surrogates In the vast array of catalytic carbon-carbon bond forming reactions, the Suzuki-Miyaura protocol has proven to be a particularly attractive method.  The organoborane nu...
Keywords: Addition reactions, Catalysis, Coupling reactions, Cross couplings, Halogenations, Suzuki-Miyaura coupling

Peer-Reviewed Papers
15

References

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