What Is Diphenylmethane?
Diphenylmethane, also known as methylenedibenzene or benzylphenyl, is an organic compound with the chemical formula C13H12. It’s an aromatic hydrocarbon characterized by two phenyl groups replacing two hydrogen atoms of methane. Its CAS registration number is 101-81-5, and the univalent substituent with one hydrogen removed is specifically called the benzhydryl group.
Uses of Diphenylmethane
Diphenylmethane and its derivatives serve as substructures in various substances, particularly dyes. These derivatives are employed as raw materials for inks and dyes, with dyes made from them assigned numbers in the 41,000 range in the Color Index. Additionally, certain diphenylmethane derivatives are utilized in diabetes treatment due to their reported inhibitory effects on human SGLT2 activity and reduction of urinary glucose excretion in animals.
Properties of Diphenylmethane
Diphenylmethane has a molecular weight of 168.23, a melting point of 22-25.9°C, and a boiling point of 264°C. It appears as white needle-like crystals with an orange odor at room temperature, having a density of 1.006 g/mL. While nearly insoluble in water, it dissolves readily in ethanol and non-polar organic solvents.
Types of Diphenylmethane
Diphenylmethane is primarily sold as a reagent for research and development, available in volumes ranging from 25g to 500g. Reagent-grade products are stored below 25°C by various manufacturers.
Other Information on Diphenylmethane
1. Diphenylmethane Synthesis
Diphenylmethane is synthesized via the Friedel-Crafts reaction of benzyl chloride with benzene in the presence of a Lewis acid like aluminum chloride.
2. Reactivity of Diphenylmethane
The methylene group of diphenylmethane has an acid dissociation constant pKa of 33, making it deprotonatable by sodium amide and alkylatable with alkyl halides. This reaction proceeds with a high yield regardless of the halide’s primary or secondary nature.
Diphenylmethane is photosensitive and decomposes upon contact with strong oxidizers, producing carbon monoxide and dioxide gases. Hence, it should be stored away from strong oxidizers, high temperatures, and direct sunlight, ideally in a light-shielded container in a cool, well-ventilated area below 25°C (77°F).
3. Safety and Regulations
While not subject to specific designation under certain safety laws, proper handling of diphenylmethane is essential. It requires appropriate personal protective equipment, including gloves, protective glasses, and long-sleeved clothing, along with local exhaust ventilation. Regulations regarding its transport and storage as hazardous materials should also be followed.