Diphenylmethanol

Diphenylmethanol[1]
Diphenylmethanol
Names
Preferred IUPAC name
Diphenylmethanol
Other names
Benzhydrol
Diphenylcarbinol
Hydroxydiphenylmethane
Identifiers
CAS Number
  • 91-01-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:156087
ChemSpider
  • 6770 checkY
ECHA InfoCard 100.001.849 Edit this at Wikidata
EC Number
  • 202-033-8
PubChem CID
  • 7037
UNII
  • S4HQ1H8OWD checkY
CompTox Dashboard (EPA)
  • DTXSID2059015 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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)
Solubility in water
 0.5 g/L (20 °C)
Magnetic susceptibility (χ)
 -119.1·10−6 cm3/mol
Hazards[2]
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Warning
Hazard statements
 H315, H319, H335
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 [77 °F], 100 kPa).
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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[citation needed]. An alternative method involves reducing benzophenone with sodium borohydride or with zinc dust or with sodium amalgam and water.[3]

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[4] 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[permanent dead link]
  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