3,4-Dibenzyloxybenzaldehyde
[CAS# 5447-02-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic aldehyde (containing acetal, hemiacetal)
• Name: 3,4-Dibenzyloxybenzaldehyde
• Synonyms: 3,4-Bis(benzyloxy)benzaldehyde
• Molecular Formula: C₂₁H₁₈O₃
• Molecular Weight: 318.37
• CAS Registry Number: 5447-02-9
• EC Number: 226-662-2
• SMILES: C1=CC=C(C=C1)COC2=C(C=C(C=C2)C=O)OCC3=CC=CC=C3

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 91-94 (decomp.) °C (Expl.)
• Index of Refraction: 1.623, Calc.^*
• Boiling Point: 492.4±35.0 °C (760 mmHg), Calc.^*
• Flash Point: 243.9±12.4 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS08;GHS09 Warning
• Risk Statements: H341-H410
• Safety Statements: P203-P273-P280-P318-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Germ cell mutagenicity	Muta.	2	H341

Discovery and Applications

3,4-Dibenzyloxybenzaldehyde is an aromatic aldehyde derivative characterized by two benzyloxy groups attached to the benzene ring at the 3- and 4-positions. Its chemical structure combines the reactivity of the aldehyde group with the stability and electron-donating effects of the benzyloxy substituents, making it a valuable compound in synthetic organic chemistry. The development and utilization of this compound align with the increasing demand for functionalized aromatic aldehydes in research and industrial applications.

The discovery of 3,4-dibenzyloxybenzaldehyde is rooted in efforts to modify natural phenolic compounds for enhanced chemical versatility. By introducing benzyloxy groups, the reactivity of the parent compound is fine-tuned, enabling selective functionalization and improved handling. The compound is synthesized via benzylation of hydroxybenzaldehydes, followed by purification steps to ensure high purity and yield. These synthetic strategies highlight the role of protective groups in controlling reactivity during multi-step organic syntheses.

One of the primary applications of 3,4-dibenzyloxybenzaldehyde is as a precursor in the synthesis of more complex organic molecules. Its aldehyde functionality allows it to participate in diverse chemical reactions, such as condensation, reduction, and cyclization. In particular, it is frequently used in the preparation of heterocyclic compounds, which are integral to pharmaceutical development. The compound’s benzyloxy groups also serve as removable protecting groups, providing synthetic flexibility in multi-step sequences.

In medicinal chemistry, 3,4-dibenzyloxybenzaldehyde plays a role in the synthesis of bioactive molecules, including those with antioxidant, antimicrobial, and anti-inflammatory properties. The benzyloxy substituents impart lipophilicity and steric bulk, often enhancing the biological activity and pharmacokinetic profiles of the resulting derivatives. The compound’s versatility makes it a valuable intermediate in the development of potential therapeutic agents.

The material’s applications extend to polymer and materials science, where it is utilized as a building block for the synthesis of advanced materials. The aromatic core and functional groups enable the creation of polymers with specific optical and electronic properties. These materials find applications in fields such as organic electronics, coatings, and advanced composites, underscoring the broad utility of 3,4-dibenzyloxybenzaldehyde.

Analytically, 3,4-dibenzyloxybenzaldehyde is employed as a reagent in spectroscopic and chromatographic studies. Its defined structure and reactivity make it suitable for calibration standards and as a test compound in method development. The compound’s stability and solubility in organic solvents facilitate its use in various analytical applications.

In summary, 3,4-dibenzyloxybenzaldehyde is a multifunctional compound whose discovery has significantly impacted synthetic chemistry and material development. Its applications in pharmaceuticals, materials science, and analytical chemistry underscore its importance as a versatile aromatic aldehyde derivative.

References

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DOI: 10.1007/s11101-024-09929-9

2020. Novel metallophthalocyanines with bulky 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents. Monatshefte für Chemie - Chemical Monthly, 151(9).
DOI: 10.1007/s00706-020-02639-w

2001. Synthesis of 8-C-glucosylflavones. Carbohydrate Research, 334(2).
DOI: 10.1016/s0008-6215(01)00192-6