Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

A14257 Benzeneboronic acid, 98+%

CAS Number
98-80-6
Synonyms
Phenylboric acid
Phenylboronic acid

Stock No. Size Price ($) Quantity Availability
A14257-09 10g 29.70
A14257-18 50g 71.10
A14257-30 250g 264.00
Add to Cart Add to Quote Request View Item

Benzeneboronic acid, 98+%

MDL
MFCD00002103
EINECS
202-701-9

Chemical Properties

Formula
C6H7BO2
Formula Weight
121.93
Melting point
214-219°
Storage & Sensitivity
Hygroscopic. Store under Argon. Ambient temperatures.
Solubility
Slightly soluble in water.

Applications

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.

Notes

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

Literature References

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 Hazard and Precautionary Statements

Hazard Statements: H302

Harmful if swallowed.

Precautionary Statements: P264-P270-P301+P312-P304+P312-P305+P351+P338-P312-P330-P337+P313-P501c

Wash thoroughly after handling. Do not eat, drink or smoke when using this product. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF INHALED: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If eye irritation persists: Get medical advice/attention. Dispose of contents/ container to an approved waste disposal plant

Other References

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

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware