CAS 153766-81-5|potassium trifluoro(phenyl)boranuide|Potassium phenyltrifluoroborate|potassium ion trifluoro(phenyl)boranuide|Potassium trifluoro(phenyl)borate|potassium trifluoro(phenyl)boranuide|苯...

General Information

Structure

Molecular Formula

C₆H₅BF₃K

Molecular Mass

184.0084096

Exact Mass

184.0073469

Charge

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

Canonic Smiles

F[B-](c1ccccc1)(F)F.[K+]

Isomeric Smiles

[B-](c1ccccc1)(F)(F)F.[K+]

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

2.1297

LogD (pH = 7.4)

2.1297

Log P

2.1297

Molar Refractivity

29.9782

Polarizability

11.8859

Polar Surface Area

0.0

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

potassium trifluoro(phenyl)boranuide

Synonyms

Potassium phenyltrifluoroboratePotassium trifluoro(phenyl)boratePhenyltrifluoroboric acid potassium salt苯基三氟硼酸钾Benzenetrifluoroboric acid potassium saltPotassium phenyltrifluoroborate

IUPAC Traditional name

potassium ion trifluoro(phenyl)boranuide potassium trifluoro(phenyl)boranuide

Names and Identifiers

Registration numbers

MDL Number

CAS Number

PubChem CID

PubChem SID

Beilstein Number

EC Number

Registration numbers

Properties

Physical Property

Melting Point

296-301°C

Product Information

Empirical Formula (Hill Notation)

C6H5BF3K

Purity

95%

95+%

98%

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

563951

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• 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).

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

potassium trifluoro(phenyl)boranuide

Synonyms

Potassium phenyltrifluoroboratePotassium trifluoro(phenyl)boratePhenyltrifluoroboric acid potassium salt苯基三氟硼酸钾Benzenetrifluoroboric acid potassium saltPotassium phenyltrifluoroborate

IUPAC Traditional name

potassium ion trifluoro(phenyl)boranuide potassium trifluoro(phenyl)boranuide

Registration numbers

MDL Number

CAS Number

PubChem CID

PubChem SID

Beilstein Number

EC Number

Properties

Physical Property

Melting Point

296-301°C

Product Information

Empirical Formula (Hill Notation)

C6H5BF3K

Purity

95%

95+%

98%

Molecule Details

Sigma Aldrich

563951

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

References

PubChem Literature

From Data Sources

• 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).

• 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).

Bioactivity

PubChem BioAssay

Molecule

ID:93979