Diphenylmethanol

Diphenylmethanol is the organic compound with the formula (C6H5)2CHOH. Also known as benzhydrol, it is a white solid and the parent member of a large class of diaryl alcohols.

Diphenylmethanol[1]
Names
IUPAC name
Diphenylmethanol
Other names
Benzhydrol
Diphenylcarbinol
Hydroxydiphenylmethane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.849
UNII
Properties
C13H12O
Molar mass 184.238 g·mol−1
Appearance White crystals
Density 1.103 g/cm3
Melting point 69 °C (156 °F; 342 K)
Boiling point 298 °C (568 °F; 571 K)
0.5 g/L (20 °C)
-119.1·10−6 cm3/mol
Hazards
R-phrases (outdated) R36 R37 R38
S-phrases (outdated) S26 S27 S28 S29 S30 S33 S35 S36
Related compounds
Related compounds
 Benzophenone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

Diphenylmethanol may be prepared by a Grignard reaction between phenylmagnesium bromide and benzaldehyde. An alternative method involves reducing benzophenone with sodium borohydride or with zinc dust or with sodium amalgam and water.[2]

Uses and safety

It has uses in perfume and pharmaceutical manufacture. In perfumery it is used as a fixative. In pharmaceutical manufacture it is used in the synthesis of antihistamines / antiallergenic agents and antihypertensive agents . It is used in the synthesis of Modafinil[3] and the benzhydryl group is present in the structure of many histamine H1 antagonists like diphenylhydramine. Benzhydrol is also used in the production of agrochemicals as well as other organic compounds and as a terminating group in polymerizations.

Diphenylmethanol is an irritant to the eyes, skin and respiratory system.

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References
  1. MSDS
  2. Wiselogle, F. Y.; Sonneborn, III, H. (1928). "Benzohydrol". Organic Syntheses. 8: 23. doi:10.15227/orgsyn.008.0024.
  3. EP 1583739
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