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153766-81-5 - Potassium phenyltrifluoroborate, 98% - Benzenetrifluoroboric acid potassium salt - Phenyltrifluoroboric acid potassium salt - L17568 - Alfa Aesar

L17568 Potassium phenyltrifluoroborate, 98%

CAS Number
153766-81-5
Synonyms
Benzenetrifluoroboric acid potassium salt
Phenyltrifluoroboric acid potassium salt

Size Price ($) Quantity Availability
1g 26.90
5g 77.30
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Potassium phenyltrifluoroborate, 98%

MDL
MFCD01318172
EINECS
000-000-0

Chemical Properties

Formula
C6H5BF3K
Formula Weight
184.00
Melting point
296-301°
Solubility
Soluble in water.

Applications

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. Suzuki Cross-Coupling are conducted using organotrifluoroborates as a potent boronic acid surrogates. 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.

Notes

Store in cool dry conditions in well sealed containers. Incompatible with strong oxidizing agents.

Literature References

Alexander K.L. Yuen.; Craig A. Hutton. Deprotection of pinacolyl boronate esters via hydrolysis of intermediate potassium trifluoroborates.Tetrahedron Lett. 2005, 46 (46),7899-7903 .

George W. Kabalk.; Mohammad Al-Masum. Microwave enhanced cross-coupling reactions involving potassium organotrifluoroborates.Tetrahedron Lett. 2005, 46 (37),6329-6331 .

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
7782070
Harmonized Tariff Code
2931.90
TSCA
No

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