721042

3-Carboxy-5-Nitrophenylboronsäure

• Synonym(e): 3-Borono-5-nitrobenzoesäure, 3-Carboxy-5-nitrobenzolboronsäure, 5-Carboxy-3-nitrobenzolboronsäure
• Empirische Formel (Hill-System): C₇H₆BNO₆
• CAS-Nummer: 101084-81-5
• Molekulargewicht: 210.94
• MDL-Nummer: MFCD00757433
• UNSPSC-Code: 12352103
• PubChem Substanz-ID: 329763815
• NACRES: NA.22

Eigenschaften

• Form: solid
• Qualitätsniveau: 100
• mp (Schmelzpunkt): 248-252 °C
• Funktionelle Gruppe: 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)
• InChIKey: WNIFCLWDGNHGMX-UHFFFAOYSA-N

Beschreibung

Anwendung

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.[1]
• 3-Chloro-5-nitrobenzoic acid via copper-catalyzed chlorination reaction.[2]
• Aryl-clonazepam derivatives by palladium-catalyzed Suzuki Cross-coupling reaction with clonazepam in the presence of Pd as a catalyst.[3]

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

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319,H335
• P-Sätze: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable