potassium trifluoro(phenyl)boranuide

• ChemBase ID: 93979
• Molecular Formular: C6H5BF3K
• Molecular Mass: 184.0084096
• Monoisotopic Mass: 184.0073469
• SMILES: [B-](c1ccccc1)(F)(F)F.[K+]
• Canonical SMILES: F[B-](c1ccccc1)(F)F.[K+]
• InChI: InChI=1S/C6H5BF3.K/c8-7(9,10)6-4-2-1-3-5-6;/h1-5H;/q-1;+1
• InChIKey: DVAFPKUGAUFBTJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium trifluoro(phenyl)boranuide
• IUPAC Traditional name: potassium ion trifluoro(phenyl)boranuide; potassium trifluoro(phenyl)boranuide
• Synonyms: Potassium phenyltrifluoroborate; Potassium phenyltrifluoroborate; Potassium trifluoro(phenyl)borate; Benzenetrifluoroboric acid potassium salt; Phenyltrifluoroboric acid potassium salt; 苯基三氟硼酸钾

Database IDs

• CAS Number: 153766-81-5
• EC Number: 000-000-0
• MDL Number: MFCD01318172
• Beilstein Number: 7782070
• PubChem SID: 24880142; 162080634
• PubChem CID: 23675248

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.1297
• LogD (pH = 7.4): 2.1297
• Log P: 2.1297
• Molar Refractivity: 29.9782 cm^3
• Polarizability: 11.8859 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 296-301°C; 296-301°C

Safety Information

• Storage Warning: Irritant
• 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: 95%; 95+%; 98%
• Empirical Formula (Hill Notation): C6H5BF3K

DETAILS

Sigma Aldrich - 563951

Packaging
1, 5 g in poly bottle
Protocols & Applications
Suzuki Cross-Coupling using Organotrifluoroborates as Potent Boronic Acid Surrogates

REFERENCES

• Treatment with TMS chloride in acetonitrile generates the Lewis acid phenylboron difluoride in situ, avoiding the need to handle boron trihalides: J. Org. Chem., 60, 3020 (1995).
• Aryltrifluoroborate salts are more nucleophilic than the corresponding arylboronic acids and undergo ligand-free Pd-catalyzed cross-coupling reactions with arenediazonium tetrafluoroborates to give good yields of biaryls: Tetrahedron Lett., 38, 4393 (1997); Eur. J. Org. Chem., 1875 (1999). Cross-coupling with aryl or heteroaryl halides and triflates, under ligand-free conditions, has subsequently been reported: Org. Lett., 4, 1867 (2002).
• Coupling with diaryliodonium salts has also been reported: Synth. Commun., 29, 2457 (1999). The method has been extended to the synthesis of benzophenones by carbonylative cross-coupling in the presence of CO: J. Chem. Res. (Synop.), 400 (1999).
• In the presence of Dicarbonyl(2,4-pentanedionato)rhodium(I), 39295, K aryl- and alkenyltrifluoroborates add to aldehydes and enones to give secondary alcohols and saturated ketones, respectively: Org. Lett., 1, 1683 (1999):
  
• Asymmetric Rh-catalyzed additions to enones in the presence of a chiral BINAP catalyst give the corresponding saturated ketones in high yield and ee: Eur. J. Org. Chem., 3552 (2002).