Triphenylmethane
- S-3-PHARMACEUTICAL-ORGANIC-CHEMISTRY
- Feb 28
- 1 min read
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Structure of Triphenylmethane
Triphenylmethane has a central carbon atom bonded to three phenyl groups. Its molecular formula is C19H16.
Synthesis
Friedel-Crafts Alkylation
Reaction: Benzene reacts with chloroform in the presence of aluminum chloride to form triphenylmethane.
3C6H6 + CHCl3 → AlCl3 (reagents) → C(C6H5)3 + 3HCl3
Grignard Reaction
Reaction: Benzophenone reacts with phenylmagnesium bromide to form triphenylmethane.
C6H5COC6H5 + C6H5MgBr → C(C6H5)3 + MgBrOH
Reactions
Oxidation
Triphenylmethane can be oxidized to triphenylmethyl carbocation, which is a colored intermediate in the formation of triphenylmethane dyes.
C(C6H5)3 → [O]C + (C6H5)3 + e−
Electrophilic Substitution
Nitration: Triphenylmethane can be nitrated to produce nitrotriphenylmethane.
C(C6H5)3 + HNO3 → H2SO4 (reagents) → NO2C6H4C(C6H5)2 + H2O
Medicinal Uses
Dyes: Many triphenylmethane derivatives are used as dyes, some of which have been used in medicine. For example, gentian violet (a triphenylmethane dye) is used as an antiseptic.
Other Derivatives: Some derivatives of triphenylmethane have been explored for their potential as antitumor and antimicrobial agents.
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