Diphenylmethane

Diphenylmethane
Diphenylmethane
Are common
Chem. formula	C 13 H 12
Physical properties
Molar mass	168.234 g / mol
Density	1.006 g / cm³
Thermal properties
T. melt.	22-24 ° C
T. bale.	264 ° C
Classification
Reg. CAS number	101-81-5
PubChem
Reg. EINECS number
Smiles
Inchi
Chebi
ChemSpider

Diphenylmethane is an organic compound of the hydrocarbon class, a methane derivative in the molecule of which two hydrogen atoms are replaced by phenyl groups. The diphenylmethane radical ((C ₆ H ₅ ) ₂ CH-) - benzhydryl .

Content

Physical and chemical properties

Diphenylmethane is a colorless transparent crystals with the smell of geranium, insoluble in water, but well soluble in organic solvents ( benzene , diethyl ether , chloroform ) and liquid sulfur dioxide .

Due to the presence of a methylene group and benzene rings, diphenylmethane has the properties of both aliphatic and aromatic compounds: the hydrogen atoms in the methylene group are able to be replaced by halogen atoms, a nitro group or other functional groups:

{\mathsf {(C_{6}H_{5})_{2}CH_{2}{\xrightarrow[{170^{o}t}]{PCl_{5}}}(C_{6}H_{5})_{2}CCl_{2}}}

{\ displaystyle {\ mathsf {(C_ {6} H_ {5}) _ {2} CH_ {2} {\ xrightarrow [{170 ^ {o} t}] {PCl_ {5}}} (C_ {6} H_ {5}) _ {2} CCl_ {2}}}}

oxidize to a carbonyl group with the formation of benzophenone :

{\mathsf {(C_{6}H_{5})_{2}CH_{2}{\xrightarrow[{}]{H_{2}CrO_{4}}}+(C_{6}H_{5})_{2}CO}}

{\ displaystyle {\ mathsf {(C_ {6} H_ {5}) _ {2} CH_ {2} {\ xrightarrow [{}] {H_ {2} CrO_ {4}}} + (C_ {6} H_ {5}) _ {2} CO}}}

Dehydrogenation of diphenylmethane over a platinum catalyst leads to fluorene , hydrogenation over nickel to dicyclohexylmethane.

The benzene rings of the diphenylmethane molecule enter into electrophilic substitution reactions at the 2, 2 ', 4, 4', 6, 6 'positions.

Synthesis Methods

From benzyl chloride and benzene in the presence of aluminum chloride ^[1] :

{\mathsf {C_{6}H_{5}CH_{2}Cl+C_{6}H_{6}{\xrightarrow[{}]{AlCl_{3}}}(C_{6}H_{5})_{2}CH_{2}+HCl}}

{\ displaystyle {\ mathsf {C_ {6} H_ {5} CH_ {2} Cl + C_ {6} H_ {6} {\ xrightarrow [{}] {AlCl_ {3}}} (C_ {6} H_ { 5}) _ {2} CH_ {2} + HCl}}}

From benzene and dichloromethane in the presence of aluminum chloride :

{\mathsf {CH_{2}Cl_{2}+2C_{6}H_{6}{\xrightarrow[{}]{AlCl_{3}}}(C_{6}H_{5})_{2}CH_{2}+2HCl}}

{\ displaystyle {\ mathsf {CH_ {2} Cl_ {2} + 2C_ {6} H_ {6} {\ xrightarrow [{}] {AlCl_ {3}}} (C_ {6} H_ {5}) _ { 2} CH_ {2} + 2HCl}}}

There is also a method for the synthesis of diphenylmethane from benzene and formaldehyde in an environment of 85% sulfuric acid .

Application

Diphenylmethane is used as a solvent in the paint industry and as a perfume for soaps. A number of diphenylmethane derivatives serve as pesticides , fungicides and bactericides .

Notes

↑ WW Hartman and Ross Phillips (1943). "Diphenylmethane." Org. Synth .; Coll. Vol. 2: 232.

Literature

Chemical Encyclopedia / Editorial Board: Knunyants I.L. et al. - M .: Soviet Encyclopedia, 1990. - T. 2 (Daf-Med). - 671 p. - ISBN 5-82270-035-5 .

[1] WW Hartman and Ross Phillips (1943). "Diphenylmethane." Org. Synth .; Coll. Vol. 2: 232.

Diphenylmethane

Are common
Chem. formula	C ₁₃ H ₁₂
Physical properties
Molar mass	168.234 g / mol
Density	1.006 g / cm³
Thermal properties
T. melt.	22-24 ° C
T. bale.	264 ° C
Classification
Reg. CAS number	101-81-5
PubChem
Reg. EINECS number
Smiles
Inchi
Chebi
ChemSpider