Diphenylmethane

Diphenylmethane is an organic compound with the formula (C6H5)2CH2 (often abbreviated CH
2Ph
2). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white solid.

Names
Preferred IUPAC name
1,1′-Methylenedibenzene[1]
Other names
Diphenylmethane
Benzylbenzene
Identifiers
3D model (JSmol)
Abbreviations BnPh, Ph2CH2
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.708
MeSH Diphenylmethane
UNII
  • InChI=1S/C13H12/c1-3-7-12(8-4-1)11-13-9-5-2-6-10-13/h1-10H,11H2 Y
    Key: CZZYITDELCSZES-UHFFFAOYSA-N Y
  • InChI=1/C13H12/c1-3-7-12(8-4-1)11-13-9-5-2-6-10-13/h1-10H,11H2
    Key: CZZYITDELCSZES-UHFFFAOYAV
  • c1c(cccc1)Cc2ccccc2
Properties
C13H12
Molar mass 168.234
Appearance colourless oil
Density 1.006 g/mL
Melting point 22 to 24 °C (72 to 75 °F; 295 to 297 K)
Boiling point 264 °C (507 °F; 537 K)
14 mg/L
Acidity (pKa) 33
-115.7·10−6 cm3/mol
Hazards
Main hazards flammable
Flash point > 110 °C; 230 °F; 383 K
Related compounds
Related compounds
 Diphenylmethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Diphenylmethane is a common skeleton in organic chemistry. The diphenylmethyl group is also known as benzhydryl.

Synthesis

It is prepared by the Friedel–Crafts alkylation of benzyl chloride with benzene in the presence of a Lewis acid such as aluminium chloride:[2]

C6H5CH2Cl + C6H6 → (C6H5)2CH2 + HCl

Reactivity of the C-H bond

The methylene group in diphenylmethane is mildly acidic with a pKa of 32.2. The resulting carbanion can be alkylated:[3]

(C6H5)2CH2 + NaNH2 → (C6H5)2CHNa + NH3
(C6H5)2CHNa + RBr → (C6H5)2CHR + NaBr

The Ph2CH-H bond is weak, with a bond dissociation energy of 82 kcal/mol.[4]

See also

References
  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 452. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. W. W. Hartman and Ross Phillips (1934). "Diphenylmethane". Organic Syntheses. 14: 34. doi:10.15227/orgsyn.014.0034.
  3. Murphy, William S.; Hamrick, Phillip J.; Hauser, Charles R. (1968). "1,1-Diphenylpentane". Organic Syntheses. 48: 80. doi:10.15227/orgsyn.048.0080.
  4. . doi:10.1021/ja00051a010. Cite journal requires |journal= (help); Missing or empty |title= (help)


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