Triphenylmethanol

Triphenylmethanol

Names
IUPAC name Triphenylmethanol
Other names Triphenylcarbinol Tritanol
Identifiers
CAS Registry Number	76-84-6 Y
ChEMBL	ChEMBL118166 Y
ChemSpider	6215 Y
InChI InChI=1S/C19H16O/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,20H Y Key: LZTRCELOJRDYMQ-UHFFFAOYSA-N Y InChI=1/C19H16O/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,20H Key: LZTRCELOJRDYMQ-UHFFFAOYAJ
Jmol-3D images	Image
PubChem	6457
SMILES OC(c1ccccc1)(c2ccccc2)c3ccccc3
Properties
Chemical formula	C19H16O
Molar mass	260.33 g/mol
Density	1.199 g/cm3
Melting point	160 to 163 °C (320 to 325 °F; 433 to 436 K)
Boiling point	360 to 380 °C (680 to 716 °F; 633 to 653 K)
Hazards
MSDS	External MSDS
Related compounds
Related compounds	Triphenylmethane
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Triphenylmethanol (also known as triphenylcarbinol, TrOH) is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes.

Structure and Properties

Triphenylmethanol contains three phenyl rings and an alcohol group bound to a central tetrahedral carbon atom. All three C-Ph bonds are typical of sp³-sp² carbon-carbon bonds with lengths of approximately 1.47 Å, while the C-O bond length is approximately 1.42 Å.^[1]

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:^[2]

Ph₃COH + MeCOCl → Ph₃CCl + MeCO₂H

The three phenyl groups also offer steric protection. Reaction with hydrogen peroxide gives an unusually stable hydroperoxide, Ph3COOH.^[3]

Acid-base properties

As a derivative of methanol, triphenylmethanol is expected to have a pK_a in the range of 16-19. Typical of alcohols, resonance offers no stabilization of the conjugate base due to being bonded to a saturated carbon atom. Stabilization of the anion by solvation forces is largely ineffective due to the steric influence of the three phenyl groups.

On the other hand, the basicity of triphenylmethanol is enhanced due to the formation of a resonance-stabilized carbocation upon breaking of the C-O bond. After protonation of the oxygen under strongly acidic conditions, triphenylmethanol loses water to form the triphenylmethyl ("trityl") cation, e.g., triphenylmethyl hexafluorophosphate. The trityl cation is one of the easier to isolate carbocations, although it quickly reacts with water.

Synthesis

The preparation of triphenylmethanol from methyl benzoate or benzophenone and phenylmagnesium bromide is a common laboratory experiment for illustrating the Grignard reaction.^[4] An alternative starting material is diethyl carbonate.^[5]

Applications

Although not of major industrial importance, triphenylmethanol is a useful reagent in the research laboratory. Substituted derivatives of triphenylmethanol are intermediates in the production of the commercially useful triarylmethane dyes.^[6]

References