Description

6-Bromobenzo[d][1,3]dioxole-4-carbaldehyde (CAS No. 72744-55-9) is a high-purity brominated benzodioxole derivative with the molecular formula C₈H₅BrO₃. This compound features a benzodioxole core functionalized with a bromo substituent at the 6-position and an aldehyde group at the 4-position, making it a versatile intermediate for organic synthesis and pharmaceutical research. With an IUPAC name of 6-bromo-1,3-benzodioxole-4-carbaldehyde, it is supplied as a fine crystalline powder or solid with ≥95% purity (HPLC). Ideal for use in cross-coupling reactions, heterocycle synthesis, and medicinal chemistry applications, this reagent is rigorously tested for quality and stability. Store under inert conditions at 2-8°C to maintain reactivity.

Properties

• CAS Number: 72744-55-9
• Complexity: 185
• IUPAC Name: 6-bromo-1,3-benzodioxole-4-carbaldehyde
• InChI: InChI=1S/C8H5BrO3/c9-6-1-5(3-10)8-7(2-6)11-4-12-8/h1-3H,4H2
• InChI Key: GSUMLIBYYGBVMW-UHFFFAOYSA-N
• Exact Mass: 227.94221
• Molecular Formula: C8H5BrO3
• Molecular Weight: 229.03
• SMILES: C1OC2=CC(=CC(=C2O1)C=O)Br
• Topological: 35.5
• Monoisotopic Mass: 227.94221
• Synonyms: 72744-55-9, 6-Bromobenzo[d][1,3]dioxole-4-carbaldehyde, 6-BROMO-1,3-BENZODIOXOLE-4-CARBALDEHYDE, 6-bromo-2H-1,3-benzodioxole-4-carbaldehyde, MFCD04037050, SCHEMBL6541735, DTXSID10500985, GSUMLIBYYGBVMW-UHFFFAOYSA-N, AKOS015890712, 5-bromo-2,3-methylenedioxybenzaldehyde, 6-bromo-1,3-dioxaindane-4-carbaldehyde, 6-bromo-benzo[1,3]dioxole 4carbaldehyde, 6-bromo-benzo[1,3]dioxole-4-carbaldehyde, CS-0147065, D79774, EN300-6505555

Application

6-Bromobenzo[d][1,3]dioxole-4-carbaldehyde serves as a key building block in the synthesis of bioactive molecules, particularly in pharmaceutical and agrochemical research. Its aldehyde group enables condensation reactions for heterocycle formation, while the bromo substituent facilitates Suzuki-Miyaura or Buchwald-Hartwig couplings. Researchers utilize this compound in the development of benzodioxole-based ligands and enzyme inhibitors. It is also employed in material science for designing functionalized aromatic polymers.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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