Description

5-Bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine (CAS No. 507462-26-2) is a high-purity heterocyclic organic compound with the molecular formula C₇H₄BrN₃O₂. This nitro-substituted pyrrolopyridine derivative is a valuable building block in medicinal chemistry and pharmaceutical research, particularly for the synthesis of biologically active molecules. The compound features a bromo substituent at the 5-position and a nitro group at the 3-position of the fused pyrrolopyridine ring system, offering versatile reactivity for further functionalization. Supplied as a solid with ≥95% purity (HPLC), it is ideal for cross-coupling reactions, nucleophilic substitutions, and other synthetic transformations. Proper storage at 2-8°C in a tightly sealed container is recommended to ensure long-term stability.

Properties

• CAS Number: 507462-26-2
• Complexity: 220
• IUPAC Name: 5-bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine
• InChI: InChI=1S/C7H4BrN3O2/c8-4-1-5-6(11(12)13)3-10-7(5)9-2-4/h1-3H,(H,9,10)
• InChI Key: GHHWPSOGKLMSCJ-UHFFFAOYSA-N
• Exact Mass: 240.94869
• Molecular Formula: C7H4BrN3O2
• Molecular Weight: 242.03
• SMILES: C1=C(C=NC2=C1C(=CN2)[N+](=O)[O-])Br
• Topological: 74.5
• Monoisotopic Mass: 240.94869
• Synonyms: 5-Bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine, 507462-26-2, DTXSID20694581, 5-Bromo-3-nitro-1H-pyrrolo(2,3-b)pyridine, DTXCID60645330, 803-833-5, 1H-Pyrrolo[2,3-b]pyridine, 5-bromo-3-nitro-, MFCD12405111, 5-Bromo-3-nitro-7-azaindole, SCHEMBL7114099, GHHWPSOGKLMSCJ-UHFFFAOYSA-N, CS-B0571, HVA46226, AKOS022172414, DS-5980, SB14401, DA-37763, SY097326, EN300-212152, P16114, 5-Bromo-3-nitro-1H-pyrrolo[2 pound not3-b]pyridine, 5-Bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine, AldrichCPR

Application

5-Bromo-3-nitro-1H-pyrrolo[2,3-b]pyridine serves as a key intermediate in the synthesis of kinase inhibitors and other pharmacologically active compounds. Researchers utilize this scaffold in drug discovery programs targeting cancer and inflammatory diseases due to its privileged heterocyclic structure. The bromo and nitro functional groups allow for sequential palladium-catalyzed cross-coupling and reduction reactions to generate diverse analog libraries.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Precautionary Statements

• P264, P270, P301+P317, P330, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)

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