721042
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
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
form
solid
Quality Level
mp
248-252 °C
functional group
carboxylic acid, nitro
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
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:
Used 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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 721042-5G | 04061832713724 |
| 721042-1G | 04061832855967 |