Benzophenone

Benzophenone

Names
IUPAC name Diphenylmethanone
Other names Benzophenone Diphenyl ketone Benzoylbenzene Benzoylphenyl Diphenylmethanone
Identifiers
CAS Registry Number	119-61-9
Jmol-3D images	Image
SMILES O=C(c1ccccc1)c2ccccc2
Properties
Chemical formula	C13H10O
Molar mass	182.22 g/mol
Appearance	White solid
Odor	Geranium-like
Density	1.11 g/cm3 (20 °C)
Melting point	48.5 °C (119.3 °F; 321.6 K)
Boiling point	305.4 °C (581.7 °F; 578.5 K)
Solubility in water	0.0137 g/100 ml (at 25 °C)
Solubility	Soluble in glacial acetic acid, acetone, benzene, carbon disulfide, CCl4, methanol
Solubility in diethyl ether	16.6 g/100 ml
Solubility in ethanol	13.3 g/100 ml
Vapor pressure	1.93·10-3 mm Hg at 25 °C
Hazards
Safety data sheet	Sigma-Aldrich
Flash point	110 °C (230 °F; 383 K)
Related compounds
Related compounds	Acetophenone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Benzophenone is the simplest di-aryl ketone.

It is often used in drying solvents together with sodium metal, to produce a very dry solvent suitable for Grignard reagents.

Properties

Chemical

Benzophenone can be reduced by sodium metal to produce the intensely blue colored benzophenone ketyl radical. This is highly reactive towards water and oxygen so it can be used as an indicator of solvent dryness.

Benzophenone is a strong UV absorber, owing to cross-conjugation. This results in its use as a UV photoinitiator in some UV curing resins. Derivatives of benzophenone are often used in sunscreens and as an additive to prevent the UV-induced degradation of polymers and other organic compounds.

Physical

Benzophenone is a white solid, with a characteristic smell, practically insoluble in water, but more soluble in organic solvents.

Availability

Benzophenone is sold by lab suppliers. Can also be purchased from eBay.

Preparation

Benzophenone is produced by the copper-catalyzed oxidation of diphenylmethane with oxygen from air.

It can also be produced by the ketonic decarboxylation of calcium benzoate.

Projects

• Photosensitizer in photochemistry
• Water indicator in air-free techniques
• Synthesis of diphenylmethanol

Handling

Safety

Benzophenone is considered safe, but it may be irritant.

Storage

In sealed bottles.

Disposal

Can be neutralized by oxidizing it with an oxidizing solution/mixture.

References

Relevant Sciencemadness threads

• Preparation of Benzophenone
• benzophenone synthesis
• Lewis acid for benzophenone synthesis with benzoyl bromide