Methyl 3,4-diaMino-5-broMobenzoate

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Cat Number

INT1245643111

CAS Number

1245643-11-1

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Product Detail Description Customer Q&A

CAS Number

1245643-11-1

Storage

2-8℃

Synonyms

3-Bromo-5-(methoxycarbonyl)benzene-1,2-diamine, 3-Bromo-5-(methoxycarbonyl)phenylene-1,2-diamine;Methyl 3-bromo-4,5-diaminobenzoate;3,4-Diamino-5-bromo-benzoic acid methyl ester

Molecular Formula

C8H9BrN2O2

Molecular Weight

245.07

Smiles

C(OC)(=O)C1=CC(Br)=C(N)C(N)=C1

Appearance

Dark brown solid

Boiling Point

402.5℃

Relative Density

1.66

pKa

1.94

General Description

Methyl 3,4-diamino-5-bromobenzoate is a multifunctional aromatic intermediate featuring both amino groups (meta and para relative to the methyl ester) and a bromine substituent on a methyl benzoate scaffold. The ortho relationship between the amino groups enables intramolecular cyclization, while the bromine provides a site for transition-metal-catalyzed cross-coupling reactions. This combination of functional groups makes it a versatile precursor for fused heterocyclic ring systems.

Mechanism of Action

Methyl 3,4-diamino-5-bromobenzoate serves as a key intermediate in the synthesis of indoles (via Fischer indole synthesis), quinoxalines (via condensation with 1,2-dicarbonyls), benzimidazoles (via condensation with carboxylic acids or aldehydes), and other fused heterocycles. The amino groups undergo cyclocondensation reactions with electrophiles, while the aryl bromide participates in Suzuki, Heck, and Buchwald-Hartwig cross-coupling reactions under palladium catalysis.

Application

Methyl 3,4-diamino-5-bromobenzoate is used in medicinal chemistry for the synthesis of kinase inhibitors, anti-inflammatory agents, and CNS-active compounds. The benzimidazole substructure formed upon cyclization is a common motif in pharmaceutical agents targeting protein kinases, GPCRs, and ion channels. It is also employed in the synthesis of dyes, pigments, and corrosion inhibitors.

What is the recommended storage condition for Methyl 3,4-diaMino-5-broMobenzoate?

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.

What documentation is provided with each batch of Methyl 3,4-diaMino-5-broMobenzoate?

Each batch is accompanied by a Certificate of Analysis (COA) covering identity, potency, and relevant purity tests. Safety Data Sheets (SDS) are available upon request.

What functional groups in Methyl 3,4-diaMino-5-broMobenzoate 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 Methyl 3,4-diaMino-5-broMobenzoate 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.

Is Methyl 3,4-diaMino-5-broMobenzoate manufactured under GMP conditions?

It is produced in facilities operating under applicable GMP or equivalent quality standards, ensuring consistent product quality and compliance with pharmaceutical industry requirements.