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456772

Sigma-Aldrich

4-Carboxyphenylboronic acid

Synonym(s):

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

Linear Formula:
HO2CC6H4B(OH)2
CAS Number:
14047-29-1
Molecular Weight:
165.94
Beilstein:
3031088
MDL number:
MFCD00151801
UNSPSC Code:
12352103
PubChem Substance ID:
24869234
EC Index Number:
604-189-6
NACRES:
NA.22

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 Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
Glucose-Sensitivity of Boronic Acid Block Copolymers at Physiological pH
Roy, D.; Sumerlin, B. S.
ACS Macro Letters, 1, 529-532 (2012)
Jinqiang Wang et al.
Science advances, 5(7), eaaw4357-eaaw4357 (2019-07-17)
Glucose-responsive insulin delivery systems with robust responsiveness that has been validated in animal models, especially in large animal models, remain elusive. Here, we exploit a new strategy to form a micro-sized complex between a charge-switchable polymer with a glucose-sensing moiety
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