Ph3CH

Ph3CH, commonly known as triphenylmethane, is an aromatic hydrocarbon with the molecular formula C19H16. It features a central sp3 carbon bonded to three phenyl groups and one hydrogen, giving Ph3CH a tetrahedral geometry and a nonpolar character. At room temperature it is typically a colorless solid that is poorly soluble in water but dissolves in many organic solvents such as benzene, toluene, and chloroform.

The benzylic C–H bond in triphenylmethane is relatively acidic for a hydrocarbon; deprotonation yields the triphenylmethyl anion (Ph3C−), a resonance-stabilized species delocalized over the three rings. This stabilization underlies the chemistry of the trityl system, including the stability of the trityl cation (Ph3C+) used in carbocation chemistry and in protecting-group strategies.

Synthesis and occurrence: Triphenylmethane is a well-studied reference compound in physical organic chemistry. It is prepared and accessed in laboratories via routes that generate or utilize the triphenylmethyl cation, followed by reduction or substitution to the neutral hydrocarbon. It also appears as a core fragment in many triphenylmethyl derivatives.

Applications and significance: The trio of phenyl rings around the central carbon makes the trityl motif useful in chemistry. The trityl cation is a classic stabilized carbocation, and the corresponding trityl group is widely used as a protecting group for alcohols and amines in organic synthesis, being removable under acidic conditions. The Ph3CH unit thus serves as a foundational model system for benzylic acidity and resonance stabilization.

Safety: Triphenylmethane is a flammable organic compound. Handle with standard laboratory precautions to avoid inhalation or skin contact.