potassium trifluoro[(E)-2-phenylethenyl]boranuide

• ChemBase ID: 153024
• Molecular Formular: C8H7BF3K
• Molecular Mass: 210.0456896
• Monoisotopic Mass: 210.02299696
• SMILES: [B-](/C=C/c1ccccc1)(F)(F)F.[K+]
• Canonical SMILES: F[B-](/C=C/c1ccccc1)(F)F.[K+]
• InChI: InChI=1S/C8H7BF3.K/c10-9(11,12)7-6-8-4-2-1-3-5-8;/h1-7H;/q-1;+1/b7-6+
• InChIKey: NONAUTDEFRJJII-UHDJGPCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium trifluoro[(E)-2-phenylethenyl]boranuide
• IUPAC Traditional name: potassium trifluoro[(E)-2-phenylethenyl]boranuide
• Synonyms: beta-Styryltrifluoroboric acid potassium salt; Potassium trans-beta-styryltrifluoroborate; Potassium trifluoro(E)-2-phenyl-1-ethenylborate; Potassium trifluoro(E)-2-phenylethenylborate; Potassium trans-styryltrifluoroborate; 反式-β-苯乙烯三氟硼酸钾; 反式-苯乙烯基三氟硼酸钾

Database IDs

• CAS Number: 201852-49-5
• EC Number: 000-000-0
• MDL Number: MFCD02093981
• Beilstein Number: 7782992
• PubChem SID: 162247164; 24880844
• PubChem CID: 23664278

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.8751
• LogD (pH = 7.4): 2.8751
• Log P: 2.8751
• Molar Refractivity: 39.7547 cm^3
• Polarizability: 15.315548 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.); >300°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Linear Formula: C6H5(CH)2BF3K

DETAILS

Sigma Aldrich - 576158

Packaging
1, 5 g in poly bottle
Application
Reactant for:
• Suzuki-Miyaura cross-coupling1,2
• Enantioselective total synthesis of naseseazines A and B via regioselective Friedel-Crafts based arylative dimerization3
• Metal-free chlorodeboronation reactions4
• Preparation of aryl ketones via Lewis acid-catalyzed nucleophilic substitution5
• Preparation of Weinreb amides by palladium-catalyzed cross-coupling reactions6
Protocols & Applications
Suzuki Cross-Coupling using Organotrifluoroborates as Potent Boronic Acid Surrogates

REFERENCES

• Undergoes cross-coupling reactions with arenediazonium tetrafluoroborates, catalyzed by the palladacycle trans-Di-?-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II), L16948, to give substituted stilbenes in high yield: Tetrahedron Lett., 39, 5045 (1998); Eur. J. Org. Chem., 1875 (1999).