4-Bromo-1,2-(methylenedioxy)benzene CAS No. 2635-13-4

Uses

• Pharmaceuticals: Crucial precursor in the synthesis of pharmacologically active compounds with benzodioxole scaffolds (e.g., antifungal, anticancer, adrenergic receptor agonists)

• Agrochemicals: Used in the synthesis of herbicides and pesticides

• Ligands and Materials: Employed in creating complex ligands for catalysis and as a building block for advanced organic materials

• Other Applications:

  • Synthetic intermediate in household chemicals

  • Synthesis of organophosphorus ligands and drugs (e.g., piribedil)

  • Used in palladium-catalyzed coupling reactions (e.g., Heck reaction)

  • Identified as an impurity in pharmaceutical production (e.g., Paroxetine Impurity 89)

  • Applicable in proteomics research

Molecular Information

• Molecular Formula: C₇H₅BrO₂

• Molecular Weight: 201.02 g/mol

• CAS Number: 2635-13-4

• IUPAC Name: 5-bromo-1,3-benzodioxole

• Synonyms:

  • 1-Bromo-3,4-(methylenedioxy)benzene

  • 5-Bromo-1,3-benzodioxole

  • 5-Bromobenzo[d][1,3]dioxole

  • 3,4-Methylenedioxybromobenzene

Structure

• Core: Benzene ring

• Substituents:

  • Methylenedioxy group (-O-CH₂-O-) fused across positions 1 and 2, forming a 1,3-dioxole ring

  • Bromine atom attached at the para position (position 4 in the benzene ring, position 5 in the benzodioxole numbering system)

• SMILES: Brc1ccc2c(c1)OCO2

• InChI: InChI=1S/C7H5BrO2/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3H,4H2

Physical Properties

• Appearance: Yellow liquid at room temperature

• Density: 1.669 g/mL (25°C)

• Boiling Point:

  • 85-86°C (1 mmHg)

  • 228°C (atmospheric pressure)

• Melting Point: ~50-52 °C (when crystalline)

• Solubility: Soluble in common organic solvents (e.g., diethyl ether, dichloromethane, ethyl acetate, chloroform); insoluble in water

• Refractive Index: 1.584

Chemical Properties

• Spectroscopy:

  • IR Spectroscopy: Characteristic absorptions for the methylenedioxy group around 925-955 cm⁻¹ and 1030-1050 cm⁻¹; aromatic C-H stretches above 3000 cm⁻¹

  • ¹H NMR: Methylenedioxy protons as a singlet around δ 5.9 - 6.0 ppm; aromatic protons between δ 6.7 - 7.2 ppm

  • ¹³C NMR: Methylenedioxy carbon at ~95-101 ppm; aromatic carbons between 100-150 ppm

Safety and Handling

• Hazard Classification:

  • Skin Irritant (Category 2)

  • Eye Irritant (Category 2)

  • Specific Target Organ Toxicity - Single Exposure (Category 3, respiratory tract irritation)

• Precautions:

  • Follow standard laboratory safety practices

  • Avoid inhalation of dust/aerosols and contact with skin and eyes

  • Use personal protective equipment (PPE) including gloves and safety glasses

  • Work in a well-ventilated area, preferably a fume hood

• Storage:

  • Store in a cool, dry, and well-ventilated place

  • Keep away from incompatible materials like strong oxidizing agents

  • Store tightly sealed away from heat and light (due to light sensitivity)

Product Documents

• Safety Data Sheet (SDS)
• Certificate of Analysis
• Product Brochure
• Technical Data Sheet