4-Benzoylbiphenyl
[CAS# 2128-93-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 4-Benzoylbiphenyl
• Synonyms: ((1,1'-Biphenyl)-4-yl)phenylmethanone; 4-Phenylbenzophenone
• Molecular Formula: C₁₉H₁₄O
• Molecular Weight: 258.31
• CAS Registry Number: 2128-93-0
• EC Number: 218-345-2
• SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)C(=O)C3=CC=CC=C3

Properties

• Melting point: 99-103 ºC
• Boiling point: 419-420 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H332-H335
• Precautionary Statements: P261-P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Reproductive toxicity	Repr.	1B	H360
Skin sensitization	Skin Sens.	1B	H317
Skin sensitization	Skin Sens.	1	H317

Discovory and Applicatios

4-Benzoylbiphenyl, also known as p-Benzoylbiphenyl, is an organic compound that has gained significant attention in various fields of chemical research and industrial applications. The compound consists of a biphenyl core with a benzoyl group attached to the para position, which imparts unique chemical properties that make it useful in a range of applications, particularly in the development of advanced materials, pharmaceuticals, and organic electronic devices.

The discovery of 4-Benzoylbiphenyl dates back to the mid-20th century, during a period of intense exploration of biphenyl derivatives. Researchers were particularly interested in modifying the biphenyl structure to enhance its properties, such as improving thermal stability, chemical reactivity, and the ability to interact with light. The introduction of the benzoyl group into the biphenyl framework was a key innovation, as it allowed for the creation of a molecule with enhanced stability and the potential for further chemical modifications.

One of the primary applications of 4-Benzoylbiphenyl is in the field of material science, particularly in the synthesis of liquid crystals. Liquid crystals are substances that exhibit properties between those of conventional liquids and solid crystals, and they are widely used in display technologies, such as in liquid crystal displays (LCDs). 4-Benzoylbiphenyl has been studied as a component in liquid crystal mixtures, where its rigid biphenyl structure contributes to the alignment and stability of the liquid crystal phase, improving the performance and response time of LCDs. The presence of the benzoyl group further enhances the thermal stability of the liquid crystal mixtures, making them suitable for use in a wider range of temperatures.

In the pharmaceutical industry, 4-Benzoylbiphenyl has been explored as a potential intermediate in the synthesis of various biologically active compounds. The compound’s structure allows it to be functionalized in multiple ways, enabling the development of molecules with specific pharmacological properties. For example, derivatives of 4-Benzoylbiphenyl have been investigated for their potential anti-inflammatory and anticancer activities. The ability to introduce additional functional groups onto the biphenyl and benzoyl moieties makes 4-Benzoylbiphenyl a valuable starting material in medicinal chemistry, where the goal is often to create molecules with targeted biological effects.

Another significant application of 4-Benzoylbiphenyl is in the area of organic electronics. Organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs), rely on the use of organic semiconductors that can efficiently transport charge and emit light. 4-Benzoylbiphenyl has been studied for its electronic properties, particularly its ability to form stable, crystalline thin films that are essential for the performance of organic electronic devices. The rigidity of the biphenyl structure, combined with the electron-withdrawing effects of the benzoyl group, contributes to the efficient charge transport and stability of the materials used in these devices.

In addition to these applications, 4-Benzoylbiphenyl has also been used as a photoinitiator in the polymerization of various monomers. Photoinitiators are compounds that absorb light and generate reactive species, such as free radicals, that can initiate polymerization. The use of 4-Benzoylbiphenyl as a photoinitiator takes advantage of its ability to absorb UV light and undergo photochemical reactions that lead to the formation of polymers. This application is particularly important in the field of coatings, where UV-curable coatings are widely used due to their fast curing times and environmental benefits.

Despite its wide range of applications, the synthesis and handling of 4-Benzoylbiphenyl require careful consideration. The compound can be synthesized through the Friedel-Crafts acylation of biphenyl with benzoyl chloride, a reaction that requires the use of strong acids and can generate byproducts that need to be carefully managed. Additionally, like many aromatic compounds, 4-Benzoylbiphenyl is subject to strict regulations regarding its use and disposal, due to concerns about its potential environmental impact.

In conclusion, 4-Benzoylbiphenyl is a versatile compound with a range of applications in material science, pharmaceuticals, organic electronics, and polymer chemistry. Its discovery and development have paved the way for the creation of advanced materials and technologies that benefit from its unique chemical properties. As research into biphenyl derivatives continues, it is likely that new applications for 4-Benzoylbiphenyl will emerge, further highlighting its importance in modern chemistry.