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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-Nummer
153766-81-5
Synonyme
Benzenetrifluoroboric acid potassium salt
Phenyltrifluoroboric acid potassium salt

Größe Preis ($) Menge Verfügbarkeit
1g 26,90
5g 77,30
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Potassium phenyltrifluoroborate, 98%

MDL
MFCD01318172
EINECS
000-000-0

Chemische Eigenschaften

Formel
C6H5BF3K
Molmasse
184.00
Schmelzpunkt
296-301°
Löslichkeit
Soluble in water.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H315-H319-H335

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

Sicherheitshinweise: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/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. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
7782070
Harmonized Tariff Code
2931.90
TSCA
No

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