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456764

Sigma-Aldrich

3-Carboxyphenylboronic acid

≥95%

Synonym(s):

μ-Carboxyphenylboronic acid, 3-(Dihydroxyborane)benzoic acid, 3-(Dihydroxyboryl)benzoic acid, 3-Boronobenzoic acid, 3-Carboxybenzeneboronic acid

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About This Item

Linear Formula:
HO2CC6H4B(OH)2
CAS Number:
Molecular Weight:
165.94
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥95%

mp

243-247 °C (lit.)

functional group

carboxylic acid

SMILES string

OB(O)c1cccc(c1)C(O)=O

InChI

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

InChI key

DBVFWZMQJQMJCB-UHFFFAOYSA-N

Application

3-Carboxyphenylboronic acid can be used as a substrate in the preparation of:
  • Biaryl derivatives by reacting with bromoaniline through the Suzuki-Miyaura coupling reaction.
  • Boronic acid-functionalized block copolymer.
  • 1H-Imidazo[1,2-a]quinoxaline derivatives.

Other Notes

Contains varying amounts of anhydride

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Christopher G Barber et al.
Bioorganic & medicinal chemistry letters, 14(12), 3227-3230 (2004-05-20)
A series of 1-isoquinolinylguanidines are shown to be potent inhibitors of uPA with selectivity over tPA and plasmin. Potency is enhanced by the presence of a 4-halo and a 7-aryl substituent, particularly when substituted by a 3-carboxylic acid group. Compound
Heterocycles, 60, 1891-1897 (2003)
Novel rhodamine dyes via Suzuki coupling of xanthone triflates with arylboroxins
Calitree, B. D.; Detty, M. R.
Synlett, 89-92 (2010)
Di Wu et al.
Acta biomaterialia, 96, 123-136 (2019-06-28)
Locoregional chemotherapy, especially using implantable hydrogel depots to sustainably deliver chemotherapeutics at tumor site, has shown great potential for improving antitumor efficacy and reducing systemic toxicity. However, the hydrogel applications are limited by some intrinsic constraints, especially the contradiction between
Synthesis of a phenylboronic acid-functionalized thermosensitive block copolymer and its application in separation and purification of vicinal-diol-containing compounds
Wang Y, et al.
Royal Society of Chemistry Advances, 6(85), 82309-82320 (2016)

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