4-Bromo-3-(1,3-dioxolan-2-yl)phenol
[CAS# 1160182-44-4]

Identification

• Classification: API >> Special medicine >> Dermatology medication
• Name: 4-Bromo-3-(1,3-dioxolan-2-yl)phenol
• Molecular Formula: C₉H₉BrO₃
• Molecular Weight: 245.07
• CAS Registry Number: 1160182-44-4
• SMILES: C1COC(O1)C2=C(C=CC(=C2)O)Br

Properties

• Solubility: Very slightly soluble (0.86 g/L) (25 ºC), Calc.^*
• Density: 1.638±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H413
• Precautionary Statements: P264-P270-P273-P301+P312-P330-P501

Discovory and Applicatios

4-Bromo-3-(1,3-dioxolan-2-yl)phenol, a compound with notable biological activity, was discovered during a series of synthetic organic chemistry investigations aimed at developing novel molecules with potential pharmaceutical applications. The discovery process involved modifying phenolic structures to enhance their biological properties, leading to the synthesis of 4-Bromo-3-(1,3-dioxolan-2-yl)phenol. This compound attracted attention due to its unique chemical structure, which suggested potential utility in medicinal chemistry for developing drugs with antibacterial, antifungal, or anticancer properties.

The phenolic structure of 4-Bromo-3-(1,3-dioxolan-2-yl)phenol suggests potent antimicrobial activity. Phenols are known for their ability to disrupt microbial cell membranes and inhibit enzyme activity, making this compound a candidate for developing new antibacterial and antifungal agents. Studies have shown that brominated phenols exhibit broad-spectrum antimicrobial activity, and incorporating the dioxolane ring may enhance this effect, offering a novel solution to combat resistant bacterial and fungal strains.

The compound's unique structure allows it to interact with various biological targets, making it a candidate for anticancer drug development. Brominated phenols have been reported to exhibit cytotoxic effects against cancer cells, potentially through mechanisms such as apoptosis induction and inhibition of cell proliferation. Research into 4-Bromo-3-(1,3-dioxolan-2-yl)phenol could uncover new pathways for targeting cancer cells, contributing to the development of more effective and less toxic cancer therapies.

Beyond direct therapeutic applications, 4-Bromo-3-(1,3-dioxolan-2-yl)phenol can serve as a valuable intermediate in pharmaceutical synthesis. Its structure allows for further chemical modifications, enabling the creation of a variety of derivatives with enhanced or specialized biological activities. This versatility makes it a useful building block in medicinal chemistry, facilitating the development of a broad range of pharmaceuticals.

The synthesis and study of 4-Bromo-3-(1,3-dioxolan-2-yl)phenol also contribute to the broader field of organic chemistry. Understanding its reactivity and interactions with other compounds can provide insights into developing new synthetic methodologies and chemical reactions. This knowledge can be applied to create more efficient and sustainable processes in chemical manufacturing.

References

2017. Crisaborole. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-03-0295