Structure of triphenylmethanol
| IUPAC name
| Other names
|Molar mass||260.33 g/mol|
|Melting point||161–163 °C (322–325 °F; 434–436 K) |
|Boiling point||380 °C (716 °F; 653 K) |
|0.143 g/100 ml (25 °C)|
|Solubility|| Soluble in benzene, diethyl ether, ethanol, dioxane|
Insoluble in petroleum ether
|Solubility in benzene||16.5 g/100 ml (25 °C)|
|Solubility in dioxane||10 g/100 ml|
|Solubility in ethanol||5 g/100 ml|
Std enthalpy of
|Safety data sheet||Sigma-Aldrich|
| Benzyl alcohol|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Triphenylmethanol or triphenylcarbinol, is an organic compound, a tertiary alcohol with the formula (C6H5)3COH. It is sometimes abbreviated as TrOH or Ph3COH.
Triphenylmethanol is insoluble in water, but when it is treated with an acid, like concentrated sulfuric acid, it dissolves to create a bright yellow solution, due to the formation of a stable "trityl" carbocation. On dilution of the solution with more water, the color disappears, and triphenylmethanol precipitates from solution.
The presence of three adjacent phenyl groups confers special properties manifested in the reactivity of the alcohol. For example it reacts with acetyl chloride, not to give the ester, but triphenylmethyl chloride:
- Ph3COH + MeCOCl → Ph3CCl + MeCOOH
Triphenylmethanol forms 1:1 molecular complex with triphenylphosphine oxide.
Triphenylmethanol is sold by chemical suppliers.
- Synthesis of triarylmethane dyes
Triphenylmethanol is irritant.
In closed bottles.
No special disposal is required.
- Frey; Chemische Berichte; vol. 28; (1895); p. 2520
- Akiyama, Ryo; Sugaya, Mariko; Shinozaki, Hiraku; Yamamoto, Tetsuya; Synthetic Communications; (2019)
- Pepekin et al.; Bulletin of the Academy of Sciences of the USSR Division of Chemical Science; vol. 24; (1975); p. 2090
- Luzzio, Frederick A.; Moore, William J.; Journal of Organic Chemistry; vol. 58; nb. 2; (1993); p. 512 - 515