• Chemical structure of Potassium Vinyltrifluoroborate (potassium ethenyltrifluoroborate; potassium trifluoro(vinyl)borate), CAS 13682-77-4, 95% — organotrifluoroborate salt, the vinyltrifluoroborate anion (CH2=CH-BF3) with a potassium counterion (C2H3BF3K). An air- and water-stable boronic-acid surrogate used as a vinyl-transfer agent in Pd-catalyzed Suzuki–Miyaura cross-coupling to install a vinyl group on aryl and heteroaryl halides, en route to styrenes. Supplied by NorrChemica with DDP shipping. CoA and
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NorrChemica™

Potassium Vinyltrifluoroborate

CAS 13682-77-4 ≥95%

Potassium Vinyltrifluoroborate | CAS 13682-77-4 | ≥95%

Pack sizes & prices

Pack size Excl. VAT
1 g €19,84€19,84/g€24,90 incl. VAT
2 g €29,64€14,82/g€37,20 incl. VAT
5 g €43,19€8,64/g€54,20 incl. VAT
10 g €63,11€6,31/g€79,20 incl. VAT
25 g €102,95€4,12/g€129,20 incl. VAT

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Technical Specifications

CAS Number 13682-77-4
EC / EINECS Number 629-487-3
MDL Number MFCD02093335
SMILES [B-](C=C)(F)(F)F.[K+]
InChI InChI=1S/C2H3BF3.K/c1-2-3(4,5)6;/h2H,1H2;/q-1;+1
InChIKey ZCUMGICZWDOJEM-UHFFFAOYSA-N
PubChem CID 23679353
Molecular Formula C₂H₃BF₃K
Molecular Weight 133.95 g/mol
Melting Point 226–230 °C (dec.)
Solubility Soluble in water, methanol, acetone, acetonitrile, DMSO and DMF; poorly soluble in diethyl ether, hexane, toluene and dichloromethane.
Purity ≥95%
Physical Form White to off-white crystalline powder
HS Code 2931.90
Country of Origin Finland
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store in a cool, dry place in a tightly sealed container

Product Description & Scientific Applications

Potassium Vinyltrifluoroborate (potassium trifluoro(vinyl)borate, vinyl-BF3K) is a monomeric, air- and moisture-stable crystalline salt for vinyl transfer in palladium- and other metal-catalysed C–C bond formation. Free vinylboronic acid is prone to protodeboronation and equilibrates with its boroxine, leaving it neither stable nor of fixed stoichiometry, while vinyllithium and vinyl-Grignard reagents are pyrophoric and poorly tolerant of functional groups. The trifluoroborate carries none of these liabilities: it is weighed to an exact stoichiometry and handled in air.

Applications and Reactions

  • Suzuki–Miyaura vinylation: under palladium catalysis it transfers a vinyl group to aryl and heteroaryl halides and triflates, giving styrenes and vinyl heterocycles — building blocks for pharmaceutical and materials synthesis.
  • Controlled boron release: as a masked boronic acid, it hydrolyses only slowly under the aqueous, basic coupling conditions, supplying the active vinylboron species at the low concentration that clean transmetalation needs.
  • Vinylation of arenediazonium salts: palladium-catalysed coupling with arenediazonium salts, often base- and ligand-free, gives styrenes rapidly, and sequential Suzuki–Heck reactions extend this to stilbenes.
  • Beyond cross-coupling: potassium organotrifluoroborates, including alkenyl members, undergo rhodium-catalysed 1,4-addition to enones (for example, isopropenyltrifluoroborate to cyclic enones), illustrating reactivity of the BF3K family beyond classical coupling.
  • Polymer and π-conjugated materials: the vinyl unit is built into poly(arylenevinylene)-type conjugated polymers and into materials for dye-sensitised solar cells and photonic crystals.

Further Reading

For practical guidance on choosing boronic acids, boronate esters, and organotrifluoroborates as cross-coupling partners, see the NorrChemica Lab Journal article: Choosing Your Boron Source for Suzuki–Miyaura Coupling.

Shipping Destinations

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  • Worldwide: 7–14 business days, selected locations.

Safety Information

GHS Pictograms
GHS07 Harmful/Irritant
Signal Word Warning
Hazard Class Not regulated for transport
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)
H-Statements H315 - H319
P-Statements P264 - P280 - P302+P352 - P305+P351+P338 - P332+P313 - P337+P313 - P362+P364 - P501

Documentation

Safety Data Sheet Download PDF
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