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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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$34.59
10 G
$298.08

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1 G
$34.59
10 G
$298.08

About This Item

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

$34.59

List Price$43.40Save 20%

In StockDetails


Request a Bulk Order

Quality Level

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[1]
  • Induction of pH sensitivity on fluorescence lifetime of quantum dots by NIR fluorescent dyes[2]
  • Bio-supported palladium nanoparticles as phosphine-free catalyst for Suzuki reaction in water[3]
  • Chan-Lam-type Copper (Cu)-catalyzed S-arylation with aryl boronic acids at room temperature[4]

Reagent used in Preparation of
  • Isoquinolones via regioselective Suzuki-Miyaura cross-coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation[5]
  • Amprenavir-based P1-substituted bi-aryl derivatives as ultra-potent HIV-1 protease inhibitors[6]
  • Phenols via visible-light initiated aerobic oxidative hydroxylation of arylboronic acids using air as oxidant catalyzed by Ruthenium (Ru)-complex[7]
  • Glucose sensitive boronic acid-bearing block copolymers[8]
  • Trisulfonated calixarene upper-rim sulfonamido derivatives and their complexation with the trimethyllysine epigenetic mark[1]

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)


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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
Glucose-Sensitivity of Boronic Acid Block Copolymers at Physiological pH
Roy, D.; Sumerlin, B. S.
ACS Macro Letters, 1, 529-532 (2012)
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
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
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)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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