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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:
25487-66-5
Molecular Weight:
165.94
MDL number:
MFCD00036833
UNSPSC Code:
12352103
PubChem Substance ID:
24869232
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

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

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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.[1]
  • Boronic acid-functionalized block copolymer.[2]
  • 1H-Imidazo[1,2-a]quinoxaline derivatives.[3]

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCW4627
MKCV7876
MKCQ4496
MKBV3512V
MKBQ8766V

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Novel rhodamine dyes via Suzuki coupling of xanthone triflates with arylboroxins
Calitree, B. D.; Detty, M. R.
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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
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)
Identification and optimization of a novel series of indoleamine 2, 3-dioxygenase inhibitors
Markwalder JA, et al.
Bioorganic & Medicinal Chemistry Letters, 27(3), 582-585 (2017)
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