5-Bromo-1,3-benzodioxole

Product Introduction

4-Bromo-1,2-(methylenedioxy)benzene (CAS No. 2635-13-4), also known as 5-Bromo-1,3-benzodioxole, is an important aryl bromide intermediate widely used in organic synthesis, medicinal chemistry, agrochemical research, and functional materials development. The molecule combines a reactive bromine substituent with a benzodioxole scaffold, making it an excellent substrate for palladium-catalyzed cross-coupling reactions and other aromatic functionalization strategies.

As a versatile synthetic building block, this compound is frequently employed in the preparation of pharmaceutical intermediates, natural product analogs, heterocyclic compounds, and advanced functional organic materials.

Chemical Properties and Reaction Mechanism

Chemical Information

• Chemical Name: 4-Bromo-1,2-(methylenedioxy)benzene
• Synonyms: 5-Bromo-1,3-benzodioxole; 3,4-Methylenedioxybromobenzene
• CAS Number: 2635-13-4
• Molecular Formula: C₇H₅BrO₂
• Molecular Weight: 201.02
• Appearance: Clear yellow to yellow-orange liquid
• Recommended Purity: ≥98% (GC) 

Reaction Characteristics

The bromine substituent readily participates in numerous carbon–carbon and carbon–heteroatom bond-forming reactions, including:

• Suzuki–Miyaura coupling
• Stille coupling
• Negishi coupling
• Kumada coupling
• Buchwald–Hartwig amination
• Ullmann coupling

The benzodioxole ring also serves as a valuable pharmacophore and structural motif in medicinal chemistry and natural product synthesis.

Key Research Applications

1.Pharmaceutical Intermediate

Used in the synthesis of:

• Pharmaceutical intermediates
• Bioactive aromatic compounds
• Heterocyclic molecules
• Lead optimization libraries

2.Organic Synthesis

Suitable for:

• Palladium-catalyzed cross-coupling reactions
• Aromatic functionalization
• Multi-step organic synthesis
• Building substituted benzodioxole derivatives

3.Agrochemical Research

Applied in the preparation of:

• Agrochemical intermediates
• Crop protection compound libraries
• Functional aromatic derivatives

4.Functional Materials

Used in research involving:

• Organic electronic materials
• Functional aromatic molecules
• Specialty fine chemicals
• Advanced molecular building blocks

Recommended Experimental Conditions

Reaction conditions should be optimized according to the substrate and catalyst system.

Advantages

• Highly reactive aryl bromide intermediate
• Excellent substrate for cross-coupling chemistry
• Broad compatibility with palladium-catalyzed reactions
• Valuable benzodioxole scaffold
• Suitable for pharmaceutical and materials research
• High synthetic versatility

What is 4-Bromo-1,2-(methylenedioxy)benzene used for?
It is widely used as a synthetic intermediate in pharmaceutical research, organic synthesis, agrochemical development, and functional materials chemistry.

Is this compound suitable for Suzuki coupling reactions?
Yes. The bromine substituent makes it an excellent substrate for Suzuki–Miyaura cross-coupling as well as other palladium-catalyzed reactions.

What types of compounds can be synthesized from this intermediate?
It is commonly used to prepare benzodioxole derivatives, heterocyclic compounds, pharmaceutical intermediates, and functional aromatic molecules.

Why is the benzodioxole ring important?
The benzodioxole framework is frequently found in natural products, pharmaceutical candidates, agrochemicals, and functional organic molecules, making it a valuable structural motif.

Which cross-coupling reactions are compatible with this compound?
It is compatible with Suzuki, Stille, Negishi, Kumada, and Buchwald–Hartwig coupling reactions.

Can this product be used in medicinal chemistry research?
Yes. It is widely employed as a building block for lead discovery, analogue synthesis, and medicinal chemistry optimization.

How should this compound be stored?
Store it in a cool, dry, light-protected environment in a tightly sealed container. An inert atmosphere is recommended for extended storage.

Is this product intended for research use only?
Yes. This product is intended for laboratory research and development only.