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456772

Sigma-Aldrich

4-Carboxyphenylboronic acid

Sinónimos:

4-(Dihydroxyboronyl)benzoic acid, 4-(Dihydroxyboryl)benzoic acid, 4-Boronobenzoic acid, 4-Carboxybenzeneboronic acid, 4-Carboxylphenylboronic acid, 4-Hydroxycarbonylphenyl boronic acid, NSC 221170, p-Boronobenzoic acid, p-Carboxybenzeneboronic acid, p-Carboxyphenylboronic acid

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About This Item

Fórmula lineal:
HO2CC6H4B(OH)2
Número de CAS:
14047-29-1
Peso molecular:
165.94
Beilstein/REAXYS Number:
3031088
MDL number:
MFCD00151801
UNSPSC Code:
12352103
PubChem Substance ID:
24869234
EC Index Number:
604-189-6
NACRES:
NA.22

Quality Level

200

mp

220 °C (dec.) (lit.)

SMILES string

OB(O)c1ccc(cc1)C(O)=O

InChI

1S/C7H7BO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,11-12H,(H,9,10)

InChI key

SIAVMDKGVRXFAX-UHFFFAOYSA-N

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Application

Reactant involved in:
  • Condensation reactions with stabilizer chains at the surface of polystyrene latex
  • Suzuki coupling reactions
  • Esterification
  • Derivatization of polyvinylamine
  • Synthesis of isotopically labeled mercury
  • Functionalization of poly-SiNW for detection of dopamine
Reagent used for
  • Suzuki-Miyaura cross-coupling
  • Induction of pH sensitivity on fluorescence lifetime of quantum dots by NIR fluorescent dyes
  • Bio-supported palladium nanoparticles as phosphine-free catalyst for Suzuki reaction in water
  • Chan-Lam-type Copper (Cu)-catalyzed S-arylation with aryl boronic acids at room temperature

Reagent used in Preparation of
  • Isoquinolones via regioselective Suzuki-Miyaura cross-coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation
  • Amprenavir-based P1-substituted bi-aryl derivatives as ultra-potent HIV-1 protease inhibitors
  • Phenols via visible-light initiated aerobic oxidative hydroxylation of arylboronic acids using air as oxidant catalyzed by Ruthenium (Ru)-complex
  • Glucose sensitive boronic acid-bearing block copolymers
  • Trisulfonated calixarene upper-rim sulfonamido derivatives and their complexation with the trimethyllysine epigenetic mark

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Glucose-Sensitivity of Boronic Acid Block Copolymers at Physiological pH
Roy, D.; Sumerlin, B. S.
ACS Macro Letters, 1, 529-532 (2012)
Jae Kyoo Lee et al.
Proceedings of the National Academy of Sciences of the United States of America, 117(49), 30934-30941 (2020-11-25)
It was previously shown [J. K. Lee et al., Proc. Natl. Acad. Sci. U.S.A, 116, 19294-19298 (2019)] that hydrogen peroxide (H2O2) is spontaneously produced in micrometer-sized water droplets (microdroplets), which are generated by atomizing bulk water using nebulization without the
Hai Wang et al.
Journal of colloid and interface science, 590, 103-113 (2021-02-02)
The self-healing mechanism and bioelectrochemical interface properties of supramolecular gels have been rarely explored. In this context, we propose a constitutive "fibril-reorganization" model to reveal the self-healing mechanism of a series of core-shell structured guanosine-borate (GB) hydrogels and emphasize that
Xiu Ye et al.
Nanomaterials (Basel, Switzerland), 9(5) (2019-05-10)
Aggregation-induced emission (AIE) active cellulose nanocrystals (TPE-CNCs) were synthesized by attaching tetraphenylethylene (TPE) to cellulose nanocrystals (CNCs). The structure and morphology of TPE-CNCs were characterized by FT-IR, XRD, ζ-potential measurements, elemental analysis, TEM, atomic force microscopy (AFM), and dynamic laser
Muthusamy Selvaraj et al.
Analytica chimica acta, 1066, 112-120 (2019-04-28)
A new boronic acid derivative functionalized with a 4-(3-(4-(4,5-diphenyl-1H-imidazole-2-yl)phenyl)-1,2,4-oxadiazol-5-yl)phenyl (IOP) moiety was synthesized for use as a sequential "on-off-on"-type relay fluorescence probe for Fe3+ ions and F- ions with high selectivity and sensitivity under physiological conditions. The introduction of Fe3+
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