Triphenylmethanol

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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
-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.

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

  1. Frey; Chemische Berichte; vol. 28; (1895); p. 2520
  2. Akiyama, Ryo; Sugaya, Mariko; Shinozaki, Hiraku; Yamamoto, Tetsuya; Synthetic Communications; (2019)
  3. Pepekin et al.; Bulletin of the Academy of Sciences of the USSR Division of Chemical Science; vol. 24; (1975); p. 2090
  4. http://www.orgsyn.org/demo.aspx?prep=cv3p0841
  5. https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rt363m.pub2
  6. http://scripts.iucr.org/cgi-bin/paper?S0108270100007423
  7. http://www.orgsyn.org/demo.aspx?prep=cv3p0839
  8. Luzzio, Frederick A.; Moore, William J.; Journal of Organic Chemistry; vol. 58; nb. 2; (1993); p. 512 - 515

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