2,2-Difluorobenzodioxole-5-carboxaldehyde
[CAS# 656-42-8]

Identification

• Classification: Organic raw materials >> Aldehyde
• Name: 2,2-Difluorobenzodioxole-5-carboxaldehyde
• Synonyms: 2,2-Difluoro-5-formyl-1,3-benzodioxole
• Molecular Formula: C₈H₄F₂O₃
• Molecular Weight: 186.11
• CAS Registry Number: 656-42-8
• EC Number: 627-939-4
• SMILES: C1=CC2=C(C=C1C=O)OC(O2)(F)F

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*, 1.399 g/mL (Expl.)
• Index of Refraction: 1.525, Calc.^*, 1.5 (Expl.)
• Boiling Point: 210.5±40.0 °C (760 mmHg), Calc.^*, 202-203 °C (Expl.)
• Flash Point: 79.1±22.2 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2,2-Difluorobenzodioxole-5-carboxaldehyde is a chemical compound with the molecular formula C8H5F2O3. It belongs to a class of organic compounds known as difluorobenzodioxoles, which are characterized by a benzene ring fused to a dioxole structure, with two fluorine atoms at the 2,2-position of the benzene ring. The aldehyde functional group is positioned at the 5-position of the dioxole ring.

The compound was first synthesized as part of research into fluorine-containing heterocycles due to the unique properties imparted by the presence of fluorine atoms. Fluorine is highly electronegative, and its introduction into organic molecules can significantly affect the reactivity, solubility, and stability of the compounds. In particular, difluorinated aromatic compounds like 2,2-difluorobenzodioxole-5-carboxaldehyde are of interest due to their potential applications in pharmaceuticals, agrochemicals, and materials science.

2,2-Difluorobenzodioxole-5-carboxaldehyde serves as an intermediate in the synthesis of more complex organic molecules. The aldehyde group provides a reactive site for nucleophilic addition or condensation reactions, which are useful in the preparation of various derivatives. The difluorobenzodioxole structure can also undergo further functionalization to introduce additional functional groups, such as alcohols, amines, or halides, thus expanding the compound's utility in organic synthesis.

In the field of pharmaceuticals, the incorporation of fluorine atoms into aromatic compounds is often associated with enhanced biological activity, including improved pharmacokinetic properties like metabolic stability, lipophilicity, and bioavailability. Therefore, 2,2-difluorobenzodioxole-5-carboxaldehyde and its derivatives may be of interest in the development of new drug candidates, particularly those targeting specific biological pathways where fluorine substitution could provide a therapeutic advantage.

In materials science, difluorobenzodioxole derivatives, including 2,2-difluorobenzodioxole-5-carboxaldehyde, have been explored for their potential as building blocks in the design of functional materials. The unique electronic properties imparted by the fluorine atoms could be utilized to create polymers, sensors, or other materials with specialized properties, such as improved chemical resistance, high thermal stability, or tailored electronic characteristics.

Overall, 2,2-difluorobenzodioxole-5-carboxaldehyde is a versatile intermediate in organic synthesis, with applications in pharmaceuticals and materials science. Its fluorine-containing structure provides a valuable tool for designing new compounds with unique properties that are useful in various industrial and scientific fields.

References

2012. Reductive Amination by Continuous-Flow Hydrogenation: Direct and Scalable Synthesis of a Benzylpiperazine. Synthesis, 44(14).
DOI: 10.1055/s-0032-1316550

2018. Approaches for Performing Reductions under Continuous-Flow Conditions. Synthesis, 50(22).
DOI: 10.1055/s-0037-1610153

2019. With [Bis(trifluoroacetoxy)iodo]benzene. Science of Synthesis.