4-(Difluoromethoxy)-3-(cyclopropylmethoxy)benzaldehyde
[CAS# 151103-09-2]

Identification

• Classification: Organic raw materials >> Aldehyde
• Name: 4-(Difluoromethoxy)-3-(cyclopropylmethoxy)benzaldehyde
• Synonyms: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde
• Molecular Formula: C₁₂H₁₂F₂O₃
• Molecular Weight: 242.22
• CAS Registry Number: 151103-09-2
• EC Number: 864-864-8
• SMILES: C1CC1COC2=C(C=CC(=C2)C=O)OC(F)F

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.529, Calc.^*
• Boiling Point: 331.3±37.0 °C (760 mmHg), Calc.^*
• Flash Point: 149.1±21.4 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335-H341-H411
• Safety Statements: P203-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Germ cell mutagenicity	Muta.	2	H341
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

4-(Difluoromethoxy)-3-(cyclopropylmethoxy)benzaldehyde is an aromatic aldehyde that features two distinct functional groups, a difluoromethoxy group at position 4 and a cyclopropylmethoxy group at position 3 on the benzene ring. The difluoromethoxy group is electron-withdrawing, while the cyclopropylmethoxy group introduces a unique structural rigidity due to the strained cyclopropyl ring. This combination of substituents provides the compound with interesting electronic properties and makes it a valuable starting material for synthetic chemistry. The discovery of 4-(difluoromethoxy)-3-(cyclopropylmethoxy)benzaldehyde emerged from efforts to design novel aromatic aldehydes with tunable electronic characteristics for diverse applications in drug development and materials science.

The difluoromethoxy group in this compound is known for its ability to enhance the stability of molecules by providing electron-withdrawing effects. These effects can lead to increased resistance to metabolic degradation, which is beneficial in medicinal chemistry for designing bioactive compounds with improved pharmacokinetic properties. On the other hand, the cyclopropylmethoxy group introduces a unique steric influence. The strained cyclopropyl ring can lead to interesting reactivity, making this compound a useful intermediate in the synthesis of more complex molecules.

In medicinal chemistry, 4-(difluoromethoxy)-3-(cyclopropylmethoxy)benzaldehyde has shown potential as a building block for the development of novel pharmaceuticals. Its reactivity as an aldehyde makes it an ideal candidate for nucleophilic addition reactions, leading to the formation of imines and other heterocyclic structures. Researchers have explored the use of this compound in the synthesis of bioactive molecules, particularly those aimed at targeting specific enzymes or receptors. The difluoromethoxy group can provide metabolic stability, while the cyclopropylmethoxy group can enhance interactions with biological targets through unique three-dimensional structural effects.

Furthermore, this compound holds promise in the field of materials science, especially in the development of organic semiconductors and light-emitting materials. The two distinct functional groups can significantly influence the electronic properties of the molecule, making it suitable for use in optoelectronic devices. By incorporating 4-(difluoromethoxy)-3-(cyclopropylmethoxy)benzaldehyde into organic photovoltaics (OPVs) or organic light-emitting diodes (OLEDs), researchers can fine-tune the electronic structure of the materials, improving charge transport, light emission, and efficiency.

In addition, the unique combination of difluoromethoxy and cyclopropylmethoxy substituents provides opportunities for further structural modifications to create molecules with enhanced reactivity and specificity. This opens up possibilities for the design of custom molecular structures for a wide range of applications, from advanced chemical synthesis to specialized electronic materials.

In summary, 4-(difluoromethoxy)-3-(cyclopropylmethoxy)benzaldehyde is a versatile compound with significant potential in both medicinal chemistry and materials science. The unique combination of electron-withdrawing and sterically demanding groups provides it with distinctive properties that make it an attractive intermediate for drug development and the synthesis of functional materials. Ongoing research into this compound and its derivatives continues to explore its full potential across a variety of scientific fields.

References

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