Triphenylmethanol
 Structure of triphenylmethanol
| |
| Names | |
|---|---|
| IUPAC name
Triphenylmethanol
| |
| Other names
Triphenylcarbinol
Triphenylmethyl alcohol Tritanol | |
| Properties | |
| C19H16O Ph3COH (C6H5)3COH | |
| Molar mass | 260.33 g/mol |
| Appearance | White solid |
| Odor | Odorless |
| Density | 1.199 g/cm3 |
| Melting point | 161–163 °C (322–325 °F; 434–436 K) [2] |
| Boiling point | 380 °C (716 °F; 653 K) [1] |
| 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 |
| Thermochemistry | |
| Std enthalpy of
formation (ΔfH |
-3.349 kJ/mol[3] |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Related compounds | |
| Related compounds
|
Benzyl alcohol Diphenylmethanol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Triphenylmethanol or triphenylcarbinol, is an organic compound, a tertiary alcohol with the formula (C6H5)3COH. It is sometimes abbreviated as TrOH or Ph3COH.
Contents
Properties
Chemical
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:[4]
- Ph3COH + MeCOCl → Ph3CCl + MeCOOH
The three phenyl groups also offer steric protection. Reaction with hydrogen peroxide gives an unusually stable hydroperoxide, Ph3COOH.[5]
Triphenylmethanol forms 1:1 molecular complex with triphenylphosphine oxide.[6]
Physical
It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene.
Availability
Triphenylmethanol is sold by chemical suppliers.
Preparation
Triphenylmethanol can be obtained from the Grignard reaction of phenylmagnesium bromide and methyl benzoate or benzophenone in diethyl ether.[7]
Another route involves reacting triphenylmethane with chromyl chloride in tetrachloromethane at 22 °C for 30 minutes. The yield is given as 99%.[8]
Projects
- Synthesis of triarylmethane dyes
Handling
Safety
Triphenylmethanol is irritant.
Storage
In closed bottles.
Disposal
No special disposal is required.
References
- ↑ 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
- ↑ http://www.orgsyn.org/demo.aspx?prep=cv3p0841
- ↑ https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rt363m.pub2
- ↑ http://scripts.iucr.org/cgi-bin/paper?S0108270100007423
- ↑ http://www.orgsyn.org/demo.aspx?prep=cv3p0839
- ↑ Luzzio, Frederick A.; Moore, William J.; Journal of Organic Chemistry; vol. 58; nb. 2; (1993); p. 512 - 515
