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Diphenylmethanol

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Diphenylmethanol
Diphenylmethanol
Names
Preferred IUPAC name Diphenylmethanol
Other names Benzhydrol
Diphenylcarbinol
Hydroxydiphenylmethane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.849 Edit this at Wikidata
EC Number
  • 202-033-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H12O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14HKey: QILSFLSDHQAZET-UHFFFAOYSA-N
  • InChI=1/C13H12O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14HKey: QILSFLSDHQAZET-UHFFFAOYAG
SMILES
  • OC(c1ccccc1)c2ccccc2
Properties
Chemical formula C13H12O
Molar mass 184.238 g·mol
Appearance White crystals
Density 1.103 g/cm
Melting point 69 °C (156 °F; 342 K)
Boiling point 298 °C (568 °F; 571 K)
Solubility in water 0.5 g/L (20 °C)
Magnetic susceptibility (χ) -119.1·10 cm/mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds Benzophenone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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.

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 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.

References

  1. MSDS
  2. "Diphenylmethanol". pubchem.ncbi.nlm.nih.gov.
  3. Wiselogle, F. Y.; Sonneborn, III, H. (1928). "Benzohydrol". Organic Syntheses. 8: 23. doi:10.15227/orgsyn.008.0024.
  4. EP 1583739, Rose, Sebastien & Klein, Dominique, "Method for preparing methyl 2-diphenylmethylsulfinylacetate", published 2005-10-12, assigned to Organisation de Synthese Mondi 
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