Diphenylmethanol

Diphenylmethanol^[1]
Names
	Preferred IUPAC name Diphenylmethanol
	Other names Benzhydrol; Diphenylcarbinol; Hydroxydiphenylmethane
Identifiers
CAS Number	91-01-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:156087;
ChemSpider	6770 ;
ECHA InfoCard	100.001.849
EC Number	202-033-8;
PubChem CID	7037;
UNII	S4HQ1H8OWD ;
CompTox Dashboard (EPA)	DTXSID2059015 ;
	InChI InChI=1S/C13H12O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14H Key: QILSFLSDHQAZET-UHFFFAOYSA-N ; InChI=1/C13H12O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14H Key: QILSFLSDHQAZET-UHFFFAOYAG;
	SMILES 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
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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

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

[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

[1]

[2]

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Names


Preferred IUPAC name Diphenylmethanol
Other names Benzhydrol Diphenylcarbinol Hydroxydiphenylmethane
Identifiers
CAS Number	91-01-0^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:156087
ChemSpider	6770^Y
ECHA InfoCard	100.001.849
EC Number	202-033-8
PubChem CID	7037
UNII	S4HQ1H8OWD^Y
CompTox Dashboard (EPA)	DTXSID2059015
InChI InChI=1S/C13H12O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13-14H^Y Key: QILSFLSDHQAZET-UHFFFAOYSA-N^Y 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
SMILES 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
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 [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references