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98-80-6 - Benzeneboronic acid, 98+% - Phenylboric acid - Phenylboronic acid - A14257 - Alfa Aesar

A14257 Benzeneboronic acid, 98+%

CAS-Nummer
98-80-6
Synonyme
Phenylboric acid
Phenylboronic acid

Größe Preis ($) Menge Verfügbarkeit
10g 29,05
50g 67,67
250g 259,56
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Benzeneboronic acid, 98+%

MDL
MFCD00002103
EINECS
202-701-9

Chemische Eigenschaften

Formel
C6H7BO2
Molmasse
121.93
Schmelzpunkt
214-219°
Sensitivität
Hygroscopic
Löslichkeit
Slightly soluble in water.

Anwendungen

Benzeneboronic acid is widely utilized in various cross coupling reactions for example Mizoroki-Heck and Suzuki-Miyaura coupling reactions, etc. It serves as a receptor for carbohydrates, antimicrobial agents and enzyme inhibitors in biological reactions. It acts as a reagent in palladium-catalyzed stereoselective Heck-type reaction and as a catalyst in Ni(II) pincer complex and Pd(II) pyridoxal hydrazone metallacycles. It is also employed as a sensor for neutron capture therapy for cancer, transmembrane transport and bioconjugation and labeling of proteins and cell surface.

Bemerkungen

Hygroscopic. Keep container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents. Avoid moisture exposure.

Literaturverweise

Reagent for protection of diols as their cyclic boronates: J. Am. Chem. Soc., 80, 2443 (1958); Tetrahedron, 25, 477 (1969), which are also useful in GC and GC-MS. This has been utilized to trap cis-diols, in order to prevent over-oxidation during dihydroxylation reactions catalyzed by Osmium(VIII)­ oxide, 12103: Chem. Lett., 1721 (1988); J. Org. Chem., 63, 7322 (1998).

Promotes the ortho-hydroxalkylation of phenols by aldehydes. The cyclic boronate, formed via a [3,3] sigmatropic rearrangement, is the key intermediate: Synthesis, 365 (1979):

With citronellal, hexahydrocannabinoids are formed: J. Chem. Soc., Perkin 1, 605 (1992).

Acts as a template for Diels-Alder reactions, by forming boronate linkages with a hydroxydiene and a hydroxydienophile: Synthesis 1171 (1991); for Nicolaou's application to synthesis of the CD ring system of taxol, see: J. Chem. Soc., Chem. Commun., 1118 (1992); J. Am. Chem. Soc., 117, 634 (1995):

For use in the formation of an oxazaborolidine catalyst for use in enantioselective reductions, see note under (S)-(-)-ɑ,ɑ-Diphenyl­prolinol, L09217.

Forms a stable chiral acyloxyborane (CAB) catalyst with tartaric acid derivatives, which catalyze hetero Diels-Alder reactions, e.g. between aldehydes and 1-Methoxy-3-trimethyl­siloxy-1,3-butadiene, L06100, to give enantioselectively, dihydro-4-pyrone derivatives: Tetrahedron, 50, 979 (1994).

The most widely-used reaction of arylboronic acids is the Pd-catalyzed Suzuki synthesis of unsymmetrical biaryls: Synth. Commun., 11, 513 (1981):

For illustrative example, see: Org. Synth., 75, 53 (1997).

For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 2679 (2006). For further information and reviews on boronic acid chemistry, see Appendix 5.

Asoh, T. A.; Takaishi, K.; Kikuchi, A. Adhesion of poly(vinyl alcohol) hydrogels by the electrophoretic manipulation of phenylboronic acid copolymers. J. Mater. Chem. B 2015, 3 (33), 6740-6745.

Tsuchido, Y.; Sakai, Y.; Aimu, K.; Hashimoto, T.; Akiyoshi, K.; Hayashita, T. The design of phenylboronic acid azoprobe-polyamidoamine dendrimer complexes as supramolecular sensors for saccharide recognition in water. New J. Chem. 2015, 39 (4), 2620-2626.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H302-H315-H319-H335

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Sicherheitshinweise: P261-P280-P305+P351+P338-P304+P340-P362-P301+P312-P312-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. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. 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

Merck
14,1068
Beilstein
970972
Harmonized Tariff Code
2931.90
TSCA
Yes
RTECS
CY8575000

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