6-bromo-1H-indazole-3-carbaldehyde

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Cat Number

INT885271727

CAS Number

885271-72-7

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Product Detail Description Customer Q&A

CAS Number

885271-72-7

Storage

2-8℃

Synonyms

1-(6-bromo-1H-indazol-3-yl)-N,N-dimethylmethanamine;6-Bromo-1H-indazole-3-carbaldehyde

Molecular Formula

C8H5BrN2O

Molecular Weight

225.04

Appearance

Dark brown solid

Boiling Point

414.1℃

Relative Density

1.83

pKa

10.8

General Description

6-Bromo-1H-indazole-3-carbaldehyde is a brominated indazole intermediate featuring both a bromo substituent at the benzene ring (C-6) and a formyl group at the pyrazole ring (C-3) of the indazole core. The indazole bicyclic system (fused benzene and pyrazole) is a pharmacologically important scaffold with diverse biological activities, and the 3-formyl and 6-bromo substitution pattern provides multiple functional handles for further elaboration.

Mechanism of Action

6-Bromo-1H-indazole-3-carbaldehyde is used as a key intermediate in the synthesis of indazole-containing pharmaceuticals. The aldehyde group at C-3 undergoes condensation reactions with amines (Schiff base formation), active methylene compounds (Knoevenagel), and hydrazines/hydroxylamines (cyclocondensation to form pyrazole-fused systems). The indazole N-H can be alkylated or acylated, and the C-6 bromo substituent enables palladium-catalyzed cross-coupling reactions.

Application

6-Bromo-1H-indazole-3-carbaldehyde is used as an intermediate in the synthesis of kinase inhibitors (particularly ALK, Aurora kinase, and JAK inhibitors), tubulin polymerization inhibitors, and nitric oxide synthase modulators. The 3-formyl indazole scaffold is found in several clinical candidates for cancer therapy. It is also used in the synthesis of dyes, pigments, and corrosion inhibitors.

What is the recommended storage condition for 6-bromo-1H-indazole-3-carbaldehyde?

It should be stored at 2-8°C in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Can we obtain batch-specific analytical data for 6-bromo-1H-indazole-3-carbaldehyde?

Batch-specific COA documents are standard with every shipment. Additional analytical reports, including HPLC chromatograms or spectral data, may be provided upon request.

Is 6-bromo-1H-indazole-3-carbaldehyde available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

What functional groups in 6-bromo-1H-indazole-3-carbaldehyde are available for further chemical modification?

The specific reactive handles present in this intermediate can be confirmed by reviewing the technical data sheet. Our team can provide structural and reactivity information relevant to your synthetic route.

Is 6-bromo-1H-indazole-3-carbaldehyde suitable for use in regulated pharmaceutical processes?

Yes, it is manufactured under quality standards consistent with regulated pharmaceutical applications, including in-process controls and release testing aligned with industry requirements.