2,7-Dichloro-alpha-[(dibutylamino)methyl]-9H-fluorene-4-methanol
[CAS# 69759-61-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Fluorenes
• Name: 2,7-Dichloro-alpha-[(dibutylamino)methyl]-9H-fluorene-4-methanol
• Molecular Formula: C₂₃H₂₉Cl₂NO
• Molecular Weight: 406.39
• CAS Registry Number: 69759-61-1
• EC Number: 922-480-9
• SMILES: CCCCN(CCCC)CC(C1=CC(=CC2=C1C3=C(C2)C=C(C=C3)Cl)Cl)O

Safety Data

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

Discovery and Applications

2,7-Dichloro-α-[(dibutylamino)methyl]-9H-fluorene-4-methanol is a synthetic organic compound that belongs to the fluorene family. Its discovery dates back to the mid-20th century, when fluorene derivatives were being investigated for potential pharmaceutical applications. The addition of chlorine at the 2 and 7 positions, along with the dibutylaminomethyl group, gives this compound unique properties that have attracted interest from the medical and materials science communities.

The primary application of 2,7-dichloro-α-[(dibutylamino)methyl]-9H-fluorene-4-methanol is pharmaceuticals, especially as a potential antimicrobial agent. The structure of this compound enables it to interact with microbial cell membranes, exhibiting either bacteriostatic or bactericidal effects. Studies have explored its efficacy against various bacterial strains, suggesting its potential use in the development of new antibiotics.

Recent studies have investigated the antiviral properties of this compound. Its ability to interfere with viral replication machinery shows promise in developing treatments for viral infections. This makes it a candidate for further exploration in antiviral drug development.

In materials science, 2,7-dichloro-α-[(dibutylamino)methyl]-9H-fluorene-4-methanol is used to synthesize advanced organic materials. Its fluorene backbone is valuable in creating polymers and other materials with desired optical and electronic properties. These materials are integral in applications such as organic light-emitting diodes (OLEDs) and organic photovoltaics.

The compound can serve as an intermediate in the synthesis of more complex fluorene derivatives. Its unique structure, with both chlorine and dibutylamino groups, provides a versatile framework for further functionalization. This makes it useful for designing novel compounds for a variety of chemical and industrial applications.

In biochemical research, 2,7-dichloro-α-[(dibutylamino)methyl]-9H-fluorene-4-methanol is used to study the interaction of fluorene derivatives with biological systems. Its role in modulating biological activity helps researchers understand the structure-activity relationship of related compounds, aiding in drug discovery and development.

References

2011. Stability-indicating HPLC-DAD/UV-ESI/MS impurity profiling of the anti-malarial drug lumefantrine. Malaria Journal, 10.
DOI: 10.1186/1475-2875-10-51

1979. Quantitative structure-activity relationships in 1-aryl-2-(alkylamino)ethanol antimalarials. Journal of Medicinal Chemistry, 22(4).
DOI: 10.1021/jm00190a007