Diphenylmethanol

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Diphenylmethanol[1]
Diphenylmethanol
Names
IUPAC name
Diphenylmethanol
Other names
Benzhydrol
Diphenylcarbinol
Hydroxydiphenylmethane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.849 Edit this at Wikidata
  • InChI=1S/C13H12O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14H checkY
    Key: QILSFLSDHQAZET-UHFFFAOYSA-N checkY
  • InChI=1/C13H12O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14H
    Key: QILSFLSDHQAZET-UHFFFAOYAG
  • OC(c1ccccc1)c2ccccc2
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)
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).
checkY verify (what is checkY☒N ?)

Diphenylmethanol, (C6H5)2CHOH (also known as benzhydrol), is a secondary alcohol with a relative molecular mass of 184.23 g/mol. It has a melting point of 69 °C and a boiling point of 298 °C.

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[2] 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.

Preparation

Diphenylmethanol may be prepared by a Grignard reaction between phenylmagnesium bromide and benzaldehyde, or by reducing benzophenone, with sodium borohydride or with zinc dust or with sodium amalgam and water.[3]

References

  1. ^ MSDS
  2. ^ EP 1583739 
  3. ^ F. Y. Wiselogle and H. Sonneborn, III (1941). "Benzohydrol". Organic Syntheses; Collected Volumes, vol. 1, p. 90.