Diphenylmethane

Structure of Diphenylmethane:

• Diphenylmethanes consists of a methane molecule where two hydrogen atoms are replaced by two phenyl groups.
• The molecular formula is C13H12.

Synthesis of Diphenylmethane:

• Friedel-Crafts Alkylation:

  • Reaction: Benzene reacts with benzyl chloride in the presence of aluminum chloride to form diphenylmethanes.

    • $\mathrm{C_6H_6 + C_6H_5CH_2Cl \xrightarrow{AlCl_3} C_6H_5CH_2C_6H_5 + HCl}$

Reactions of Diphenylmethane:

• Oxidation:

  • Diphenylmethanes can be oxidized to benzophenone using a strong oxidizing agent.

    • $\mathrm{C_6H_5CH_2C_6H_5 + [O] \rightarrow C_6H_5COC_6H_5}$

• Electrophilic Substitution:

  • Nitration: Diphenylmethanes can be nitrated to produce nitro diphenylmethanes.

    • $\mathrm{C_6H_5CH_2C_6H_5 + HNO_3 \xrightarrow{H_2SO_4} NO_2C_6H_4CH_2C_6H_5 + H_2O}$

Derivatives:

1. Dyes: Some diphenylmethanes derivatives, like auramine, are used as dyes.
2. Pharmaceuticals: Diphenhydramine, an antihistamine, is a diphenylmethane derivative.

Medicinal Uses:

• Derivatives: Diphenylmethanes derivatives, such as benzhydryl ether, have been used as antihistamines. Diphenylmethanes are also a core structure in some drugs like methadone (an opioid) and certain antihistamines.

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