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721042

Sigma-Aldrich

3-Carboxy-5-nitrophenylboronic acid

Synonym(s):

(3-Carboxy-5-nitrophenyl)boronic acid, 3-(Dihydroxyboryl)-5-nitrobenzoic acid, 3-Borono-5-nitrobenzoic acid, 3-Carboxy-5-nitrobenzeneboronic acid, 5-Carboxy-3-nitrobenzeneboronic acid

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About This Item

Empirical Formula (Hill Notation):
C7H6BNO6
CAS Number:
Molecular Weight:
210.94
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

form

solid

Quality Level

mp

248-252 °C

SMILES string

OB(O)c1cc(cc(c1)[N+]([O-])=O)C(O)=O

InChI

1S/C7H6BNO6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3,12-13H,(H,10,11)

InChI key

WNIFCLWDGNHGMX-UHFFFAOYSA-N

Related Categories

Application

3-Carboxy-5-nitrophenylboronic acid can be used as a reactant to prepare:
  • Biaryl derivatives via Suzuki-Miyaura cross-coupling with aryl and heteroaryl halides via the formation of a C-C bond.
  • 3-Chloro-5-nitrobenzoic acid via copper-catalyzed chlorination reaction.
  • Aryl-clonazepam derivatives by palladium-catalyzed Suzuki Cross-coupling reaction with clonazepam in the presence of Pd as a catalyst.

Reactant for:
  • Copper-catalyzed chlorination
  • Parallel solid-phase synthesis of azabicyclooctylidenemethylbenzamides as μ- and d-opioid agonists

Used for:
  • Immobilization of glucose oxidase and acetylcholinesterase on boronic acid-activated silica surfaces

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Copper-catalyzed chlorination of functionalized arylboronic acids
Wu H and Hynes JJ
Organic Letters, 12(6), 1192-1195 (2010)
New biaryl-chalcone derivatives of pregnenolone via Suzuki-Miyaura cross-coupling reaction. Synthesis, CYP17 hydroxylase inhibition activity, QSAR, and molecular docking study
Al-Masoudi NA, et al.
Steroids, 101, 43-50 (2015)
Synthesis of new derivatives of aryl-clonazepam via Suzuki Cross-coupling reaction
Salman MA Al-Hussein and Abdul-Rida NA
European Journal of Chemistry, 7(2), 152-155 (2016)
Zhuojun Huang et al.
Biomaterials science, 6(9), 2487-2495 (2018-08-03)
We report here the development of hydrogels formed at physiological conditions using PEG (polyethylene glycol) based polymers modified with boronic acids (BAs) as backbones and the plant derived polyphenols ellagic acid (EA), epigallocatechin gallate (EGCG), tannic acid (TA), nordihydroguaiaretic acid

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