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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%

Numéro de CAS
153766-81-5
Synonymes
Benzenetrifluoroboric acid potassium salt
Phenyltrifluoroboric acid potassium salt

Conditionnement Prix ($) Quantité Disponibilité
1g 26,90
5g 77,30
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Potassium phenyltrifluoroborate, 98%

MDL
MFCD01318172
EINECS
000-000-0

Propriétés chimiques

Formule
C6H5BF3K
Poids moleculaire
184.00
Point de fusion
296-301°
Solubilité
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.

Références bibliographiques

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).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335

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

Mentions de prudence: 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.

Autres références

Beilstein
7782070
Code tarifaire harmonisé
2931.90
TSCA
No

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