1-(2,4-Bis(benzyloxy)phenyl)ethanone
[CAS# 22877-01-6]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 1-(2,4-Bis(benzyloxy)phenyl)ethanone
• Synonyms: 2',4'-Bis(benzyloxy)acetophenone
• Molecular Formula: C₂₂H₂₀O₃
• Molecular Weight: 332.39
• CAS Registry Number: 22877-01-6
• SMILES: CC(=O)C1=C(C=C(C=C1)OCC2=CC=CC=C2)OCC3=CC=CC=C3

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.595, Calc.^*
• Boiling Point: 511.5±40.0 ºC (760 mmHg), Calc.^*
• Flash Point: 255.5±13.8 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

1-(2,4-Bis(benzyloxy)phenyl)ethanone is an organic compound that belongs to the class of aryl ketones, featuring a benzyl group attached to the aromatic ring. The compound has a significant place in organic chemistry due to its potential as a precursor in synthetic pathways and its applications in medicinal chemistry, particularly in the development of biologically active compounds. The chemical structure consists of a phenyl group substituted with two benzyloxy groups at the 2 and 4 positions, and an ethanone group at the 1 position.

The discovery of 1-(2,4-Bis(benzyloxy)phenyl)ethanone can be traced to the growing interest in the modification of aromatic ketones for use in various chemical reactions, particularly for the synthesis of more complex organic molecules. The benzyloxy substitution pattern plays a critical role in enhancing the compound's solubility and reactivity, which is useful in various synthetic applications. Its synthesis typically involves electrophilic aromatic substitution reactions, where the benzyloxy groups are introduced to the phenyl ring using appropriate reagents and conditions.

In terms of applications, 1-(2,4-Bis(benzyloxy)phenyl)ethanone has shown promise in several areas of pharmaceutical and chemical research. One of the primary uses of this compound is in the synthesis of more complex molecules with potential biological activity. The compound’s structure makes it a versatile intermediate in the production of various bioactive molecules, such as anti-inflammatory agents, anticancer compounds, and antimicrobial substances. The presence of the benzyloxy groups enhances the compound's ability to interact with biological systems, which can be exploited in drug design and development.

Moreover, 1-(2,4-Bis(benzyloxy)phenyl)ethanone serves as a potential building block in the creation of ligands for metal-organic frameworks (MOFs) or coordination compounds. MOFs have garnered significant attention in the field of materials science due to their high surface area and tunable chemical properties, which make them ideal candidates for applications in catalysis, gas storage, and separation technologies. The ability of this compound to form stable complexes with metal ions further broadens its application in these fields.

The compound has also attracted attention in the synthesis of optoelectronic materials. Aryl ketones are known for their potential as components in organic light-emitting diodes (OLEDs) and organic solar cells (OSCs). The electronic properties of 1-(2,4-Bis(benzyloxy)phenyl)ethanone, combined with its ability to absorb light and participate in charge transfer processes, make it an attractive candidate for incorporation into organic electronic devices.

In the field of medicinal chemistry, derivatives of 1-(2,4-Bis(benzyloxy)phenyl)ethanone have been investigated for their potential antimicrobial and anticancer activities. The benzyloxy groups are known to impart some degree of stability and lipophilicity to the compound, which can improve its bioavailability and penetration into cells. Such modifications can be useful in the development of drugs targeting specific enzymes or proteins involved in disease progression, especially in conditions such as cancer and infectious diseases.

In conclusion, 1-(2,4-Bis(benzyloxy)phenyl)ethanone is an important intermediate in organic synthesis with a variety of applications in medicinal chemistry, materials science, and the production of functional organic compounds. Its chemical structure, featuring two benzyloxy groups, enhances its reactivity and solubility, making it a versatile building block in the development of new therapeutic agents and advanced materials. As research into its biological and material properties continues, this compound is expected to play a significant role in the development of novel drugs and technologies.