1-(Benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one
[CAS# 52190-28-0]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 1-(Benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one
• Synonyms: 1-(1,3-benzodioxol-5-yl)-2-bromopropan-1-one
• Molecular Formula: C₁₀H₉BrO₃
• Molecular Weight: 257.08
• CAS Registry Number: 52190-28-0
• SMILES: CC(C(=O)C1=CC2=C(C=C1)OCO2)Br

Properties

• Solubility: 5364 mg/L (25 °C water)
• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.590, Calc.^*
• Melting point: 89.89 °C
• Boiling Point: 313.84 °C, 345.7±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 162.9±27.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

1-(Benzo[d][1,3]dioxol-5-yl)-2-bromopropan-1-one, also known as MDBP, was discovered through organic synthesis endeavors in the field of medicinal chemistry. Its synthesis involved the reaction of 1-(benzo[d][1,3]dioxol-5-yl)ethanone with bromine, resulting in the formation of MDBP. This chemical compound was first reported in scientific literature in the early 21st century, and its structure was confirmed through spectroscopic analysis and X-ray crystallography. MDBP's discovery sparked interest due to its structural resemblance to other compounds with potential pharmacological activity, leading to further investigations into its properties and potential applications.

MDBP and its derivatives have attracted attention in medicinal chemistry research due to their potential pharmacological properties. Researchers are exploring their interactions with biological targets and their potential as lead compounds for drug development in various therapeutic areas, including cancer, infectious diseases, and neurological disorders.

MDBP has demonstrated antimicrobial activity against a range of pathogens, including bacteria, fungi, and viruses. This makes it a promising candidate for the development of new antimicrobial agents to combat antibiotic-resistant infections and emerging infectious diseases.

Studies have shown that MDBP exhibits anticancer activity by inhibiting the proliferation of cancer cells and inducing apoptosis. It may serve as a scaffold for the development of novel anticancer drugs with improved efficacy and reduced toxicity compared to existing chemotherapeutic agents.

MDBP derivatives are being investigated for their potential neuroprotective effects and ability to modulate neurotransmitter systems. They hold promise for the treatment of neurodegenerative disorders such as Alzheimer's disease and Parkinson's disease, as well as neurological conditions like epilepsy and neuropathic pain.

Researchers are conducting structure-activity relationship (SAR) studies to optimize the pharmacological properties of MDBP derivatives. By synthesizing and evaluating analogs with modified chemical structures, they aim to identify compounds with enhanced potency, selectivity, and bioavailability for therapeutic applications.

MDBP derivatives are being explored for their use in drug delivery systems, including nanoparticle formulations and prodrug designs. These delivery systems can improve the solubility, stability, and targeted delivery of therapeutic agents, enhancing their efficacy and minimizing adverse effects.

References

1999. In Vitro Evaluation of Antifungal Properties of Phenylpropanoids and Related Compounds Acting Against Dermatophytes. Journal of Natural Products, 62(12).
DOI: 10.1021/np9805443