4-Isopropyl-3,5-dimethoxybenzaldehyde
[CAS# 344396-19-6]

Identification

• Name: 4-Isopropyl-3,5-dimethoxybenzaldehyde
• Synonyms: 3,5-dimethoxy-4-propan-2-ylbenzaldehyde
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25
• CAS Registry Number: 344396-19-6
• SMILES: CC(C)C1=C(C=C(C=C1OC)C=O)OC

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.520, Calc.^*
• Boiling Point: 328.5±42.0 °C (760 mmHg), Calc.^*
• Flash Point: 143.6±14.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P302+P352-P304+P340-P321-P330-P337-P362+P364-P405-P501

Discovery and Applications

The discovery and synthesis of 4-isopropyl-3,5-dimethoxybenzaldehyde involves methods that specifically introduce specific substituents into the benzene ring. Researchers achieve this by starting the reaction from suitable precursors, such as 3,5-dimethoxybenzaldehyde and isopropyl, using aromatic substitution techniques or modifying existing benzaldehyde derivatives. This synthetic route allows for controlled modification of the benzaldehyde structure to obtain desired properties.

The benzene ring of 4-isopropyl-3,5-dimethoxybenzaldehyde is substituted with two methoxy (-OCH3) groups at the 3rd and 5th positions, an isopropyl (-CH(CH3)2) group at the 4th position, and has an aldehyde (-CHO) functional group. These substituents give it specific chemical and physical properties that influence its application in various industries.

4-isopropyl-3,5-dimethoxybenzaldehyde is a valuable organic chemistry intermediate that facilitates the synthesis of more complex molecules through reactions such as condensation, reduction, and oxidation. Its aromatic structure and functional groups enable a wide variety of transformations in chemical synthesis.

4-Isopropyl-3,5-dimethoxybenzaldehyde and its derivatives are intensively studied in pharmaceutical research for their potential biological activities. They can serve as starting points or structural motifs for the development of new drugs for various diseases.

Compounds similar to 4-Isopropyl-3,5-dimethoxybenzaldehyde are used in the flavor and fragrance industry for their aromatic characteristics and specific odors.

In research and analytical chemistry, benzaldehyde derivatives similar to this compound can serve as chemical standards or probes in analytical techniques. They help identify, quantify, and characterize related compounds in complex mixtures.

As with handling any chemical, appropriate precautions should be taken. This includes using appropriate personal protective equipment (PPE), following safe handling procedures, and ensuring compliance with regulatory guidelines for storage, use, and disposal.

References

2016. Addressing the Challenges in Suzuki-Miyaura Cross-Couplings by Ligand Design. Synlett, 27(13).
DOI: 10.1055/s-0035-1562360