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
• Empirical Formula (Hill Notation): C₇H₆BNO₆
• CAS Number: 101084-81-5
• Molecular Weight: 210.94
• MDL number: MFCD00757433
• UNSPSC Code: 12352103
• PubChem Substance ID: 329763815
• NACRES: NA.22

Properties

• form: solid
• Quality Level: 100
• 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

Description

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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable