Diphenylmethanol

Last updated
Diphenylmethanol [1]
Diphenylmethanol.png
Diphenylmethanol-from-xtal-3D-bs-17.png
Names
Preferred IUPAC name
Diphenylmethanol
Other names
Benzhydrol
Diphenylcarbinol
Hydroxydiphenylmethane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.849 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-033-8
PubChem CID
UNII
  • InChI=1S/C13H12O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14H Yes check.svgY
    Key: QILSFLSDHQAZET-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceWhite 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 [2]
GHS labelling:
GHS-pictogram-exclam.svg
Warning
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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.

Related Research Articles

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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