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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

Quality Level

200

mp

220 °C (dec.) (lit.)

functional group

carboxylic acid

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR0305
MKCP9023
MKCL9429
MKCJ8726
MKCJ7862

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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
Rui Tang et al.
Journal of the American Chemical Society, 134(10), 4545-4548 (2012-03-01)
Modulation of the fluorescence lifetime (FLT) of CdTeSe/ZnS quantum dots (QDs) by near-IR (NIR) organic chromophores represents a new strategy for generating reproducible pH-sensing nanomaterials. The hybrid construct transfers the pH sensitivity of photolabile NIR cyanine dyes to highly emissive
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
Synthesis and biological evaluation of novel amprenavir-based P1-substituted bi-aryl derivatives as ultra-potent HIV-1 protease inhibitors
Yan, J.; et al.
Bioorganic & Medicinal Chemistry Letters, 22, 784-788 (2012)
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