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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:
25487-66-5
Molecular Weight:
165.94
MDL number:
MFCD00036833
UNSPSC Code:
12352103
PubChem Substance ID:
24869232
NACRES:
NA.22

assay

≥95%

mp

243-247 °C (lit.)

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

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Jumin Yang et al.
Materials science & engineering. C, Materials for biological applications, 116, 111250-111250 (2020-08-19)
Various nanoparticles as drug delivery system provide significant improvements in the cancer treatment. However, their clinical success remains elusive in large part due to their inability to overcome both systemic and tumor tissue barriers. The nanosystems with nanoproperty-transformability (surface, size
Ruiqi Zhang et al.
Analytica chimica acta, 1106, 42-51 (2020-03-09)
Functional metal-organic frameworks (MOFs) constructed via a pre-installation strategy of introducing mixed organic ligands have attracted considerable interest in various fields. In the present study, boronic acid decorated magnetic Zr-MOFs were successfully synthesized by introducing 3-carboxyphenylboronic acid ligands as fragments.
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