Triphenylmethane

Structure of Triphenylmethane:

• Triphenylmethanes have a central carbon atom bonded to three phenyl groups. Its molecular formula is C19H16​.

Synthesis of Triphenylmethane:

• Friedel-Crafts Alkylation:

  • Reaction: Benzene reacts with chloroform in the presence of aluminum chloride to form triphenylmethanes.

    • $\mathrm{3C_6H_6 + CHCl_3 \xrightarrow{AlCl_3} C(C_6H_5)_3 + 3HCl}$

• Grignard Reaction:

  • Reaction: Benzophenone reacts with phenylmagnesium bromide to form triphenylmethanes.

    • $\mathrm{C_6H_5COC_6H_5 + C_6H_5MgBr \rightarrow C(C_6H_5)_3 + MgBrOH}$

Reactions of Triphenylmethane:

• Oxidation:

  • Triphenylmethanes can be oxidized to triphenylmethyl carbocation, which is a colored intermediate in the formation of triphenylmethanes dyes.

    • $\mathrm{C(C_6H_5)_3 \rightarrow [O]C^+ (C_6H_5)_3 + e^-}$

• Electrophilic Substitution:

  • Nitration: Triphenylmethane can be nitrated to produce nitrotriphenylmethane.

    • $\mathrm{C(C_6H_5)_3 + HNO_3 \xrightarrow{H_2SO_4} NO_2C_6H_4C(C_6H_5)_2 + H_2O}$

Medicinal Uses:

• Dyes: Many triphenylmethanes derivatives are used as dyes, some of which have been used in medicine. For example, gentian violet (triphenylmethanes dye) is used as an antiseptic.
• Other Derivatives: Some derivatives of triphenylmethanes have been explored for their potential as antitumor and antimicrobial agents.

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