4-Phenyltoluene
[CAS# 644-08-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 4-Phenyltoluene
• Synonyms: 1-Methyl-4-phenylbenzene; 4-Methyl-1,1'-biphenyl; 4-Methylbiphenyl
• Molecular Formula: C₁₃H₁₂
• Molecular Weight: 168.24
• CAS Registry Number: 644-08-6
• EC Number: 211-409-0
• FEMA: 3186
• SMILES: CC1=CC=C(C=C1)C2=CC=CC=C2

Properties

• Density: 1.015 g/mL
• Melting point: 45-49 ºC
• Boiling point: 267-268 ºC
• Flash point: 110 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

4-Phenyltoluene, also known as 1-methyl-4-phenylbenzene, is an aromatic hydrocarbon characterized by a toluene core with a phenyl group attached at the para position. This compound has garnered attention in organic chemistry due to its structural attributes, making it a useful intermediate in the synthesis of various organic molecules and materials. The simplicity of its structure, combined with its chemical reactivity, allows it to serve as a key building block in multiple synthetic processes.

The synthesis of 4-phenyltoluene can be traced back to the development of classic organic reactions. One of the most straightforward methods for synthesizing 4-phenyltoluene is the Friedel-Crafts alkylation of toluene using a phenyl halide in the presence of a Lewis acid catalyst, such as aluminum chloride. This method is favored for its high yield and selectivity, particularly in forming the para-substituted isomer. The reaction typically proceeds under controlled conditions to minimize the formation of ortho and meta isomers, thereby optimizing the production of 4-phenyltoluene.

As a colorless liquid with a characteristic aromatic odor, 4-phenyltoluene exhibits several important physical properties. It has a boiling point higher than toluene due to the added bulk of the phenyl group, which also enhances its stability and makes it a valuable compound in both laboratory research and industrial applications. Its solubility in organic solvents such as benzene, toluene, and chloroform facilitates its use in various chemical processes.

In the realm of organic synthesis, 4-phenyltoluene serves as a crucial intermediate. Its structure allows it to undergo a variety of chemical transformations, including electrophilic aromatic substitution and cross-coupling reactions. These transformations enable the introduction of various functional groups, making it a versatile precursor in the synthesis of complex organic molecules. For example, 4-phenyltoluene can be used in the synthesis of pharmaceuticals, agrochemicals, and dyes, where specific functionalization of the aromatic ring is required.

In addition to its role in synthesis, 4-phenyltoluene is used in the production of advanced materials, particularly in the development of polymers and resins. Its aromatic structure contributes to the rigidity and thermal stability of polymers, making it a valuable monomer or comonomer in the production of high-performance materials. These materials find applications in coatings, adhesives, and engineering plastics, where durability and resistance to thermal and chemical degradation are essential.

The electronic properties of 4-phenyltoluene also make it a candidate for applications in organic electronics. Its conjugated system, formed by the aromatic rings, can participate in the formation of organic semiconductors. These materials are critical in the development of organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and organic field-effect transistors (OFETs). The ability to fine-tune the electronic properties of these devices through structural modifications of compounds like 4-phenyltoluene has led to advancements in the performance and efficiency of organic electronic devices.

4-Phenyltoluene has also been studied for its potential environmental impact. As with many aromatic hydrocarbons, its stability and persistence in the environment raise concerns regarding its biodegradability and potential to bioaccumulate. Research into environmentally friendly synthesis methods and potential degradation pathways continues to be an important area of study to mitigate any adverse effects associated with the widespread use of this compound.

In conclusion, 4-phenyltoluene is a significant compound in organic chemistry and material science. Its role as a synthetic intermediate, coupled with its applications in the development of advanced materials and organic electronics, highlights its versatility and importance. As research progresses, 4-phenyltoluene will likely continue to play a critical role in the synthesis of complex molecules and the development of innovative materials.