potassium ethenyltrifluoroboranuide

• ChemBase ID: 96817
• Molecular Formular: C2H3BF3K
• Molecular Mass: 133.9497296
• Monoisotopic Mass: 133.99169684
• SMILES: [B-](F)(F)(F)C=C.[K+]
• Canonical SMILES: F[B-](C=C)(F)F.[K+]
• InChI: InChI=1S/C2H3BF3.K/c1-2-3(4,5)6;/h2H,1H2;/q-1;+1
• InChIKey: ZCUMGICZWDOJEM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium ethenyltrifluoroboranuide
• IUPAC Traditional name: potassium ion ethenyltrifluoroboranuide; potassium ethenyltrifluoroboranuide
• Synonyms: potassium ethenyltrifluoroboranuide; Potassium ethenyltrifluoroborate; Potassium vinyltrifluoroborate; Potassium (ethenyl)trifluoroborate; Potassium vinyltrifluoroborate; Vinyltrifluoroboric acid potassium salt; Potassium trifluoro(vinyl)borate; 乙烯三氟硼酸钾

Database IDs

• CAS Number: 13682-77-4
• EC Number: 000-000-0
• MDL Number: MFCD02093335
• Beilstein Number: 7777570
• PubChem SID: 162083463; 24884089
• PubChem CID: 23679353

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.0586
• LogD (pH = 7.4): 1.0586
• Log P: 1.0586
• Molar Refractivity: 13.9862 cm^3
• Polarizability: 5.988023 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 223 - 225°C; 230(dec.)°C; 230°C dec.
• Hydrophobicity(logP): 0.0050

Safety Information

• Storage Warning: Corrosive; Hygroscopic
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 34; 36/37/38
• Safety Statements: 26-36/37/39-45; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: 95%; 97%
• Linear Formula: CH2=CHBF3K

DETAILS

Sigma Aldrich - 655228

Packaging
1, 5, 25, 100 g in poly bottle
Application
Organotrifluoroborate involved in:
• Suzuki Miyaura cross-coupling reactions1,2 and polymerization reactions3
• Synthesis of photonic crystals4
• Synthesis of sensitizers for dye-sensitized solar cells5
• Mannich / diastereoselective hydroamination reaction sequence6Organotrifluoroborates as versatile and stable boronic acid surrogates.
Protocols & Applications
Suzuki Cross-Coupling using Organotrifluoroborates as Potent Boronic Acid Surrogates

REFERENCES

• Stable vinylating agent. Darses et al, reported the cross-coupling reaction with arenediazonium tetrafluoroborates to give styrenes in high yield, catalyzed by Pd(OAc)₂ (ligand-free) or the palladacycle trans-Di-?-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II), L16948: Tetrahedron Lett., 39, 5045 (1998); Eur. J. Org. Chem., 1875 (1999). Molander has since described the direct cross-coupling of the reagent with aryl halides and triflates, catalyzed by [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) chloride, 41225: Org. Lett., 4, 107 (2002):