Benzophenone

Benzophenone

Names
Preferred IUPAC name Diphenylmethanone
Other names Benzophenone Phenyl ketone Diphenyl ketone Benzoylbenzene Benzoylphenyl Diphenylmethanone
Identifiers
CAS Number	119-61-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:41308 Y
ChemSpider	2991 Y
DrugBank	DB01878 Y
ECHA InfoCard	100.003.943
KEGG	C06354 Y
PubChem CID	3102
UNII	701M4TTV9O Y
InChI InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H Y Key: RWCCWEUUXYIKHB-UHFFFAOYSA-N Y InChI=1/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H Key: RWCCWEUUXYIKHB-UHFFFAOYAX
SMILES O=C(c1ccccc1)c2ccccc2
Properties
Chemical formula	C13H10O
Molar mass	182.22 g·mol−1
Appearance	White solid
Odor	Geranium-like
Density	1.11 g/cm3
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	Insoluble
Solubility in organic solvents	1 g/7.5 mL in ethanol 1 g/6 mL in diethyl ether
Magnetic susceptibility (χ)	-109.6·10−6 cm3/mol
Hazards
Main hazards	Harmful (XN)
Safety data sheet	External MSDS by JT Baker
NFPA 704	1 1 0
Flash point	110 °C (230 °F; 383 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Benzophenone is the organic compound with the formula (C₆H₅)₂CO, generally abbreviated Ph₂CO. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone.

Benzophenone can be used as a photo initiator in UV-curing applications such as inks, imaging, and clear coatings in the printing industry. Benzophenone prevents ultraviolet (UV) light from damaging scents and colors in products such as perfumes and soaps.

Benzophenone can also be added to plastic packaging as a UV blocker to prevent photo-degradation of the packaging polymers or its contents. Its use allows manufacturers to package the product in clear glass or plastic (such as a PETE water bottle). Without it, opaque or dark packaging would be required.

In biological applications, benzophenones have been used extensively as photophysical probes to identify and map peptide–protein interactions.

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

A laboratory route involves the reaction of benzene with carbon tetrachloride followed by hydrolysis of the resulting diphenyldichloromethane. It can also be prepared by Friedel-Crafts acylation of benzene with benzoyl chloride in the presence of a Lewis acid (e.g. aluminium chloride) catalyst.

Another route of synthesis is through a palladium(II)/oxometalate catalyst. This converts an alcohol to a ketone with two groups on each side.

Another, less well-known reaction to produce benzophenone is the pyrolysis of anhydrous calcium benzoate.

Benzophenone is a common photosensitizer in . It crosses from the S₁ state into the triplet state with nearly 100% yield. The resulting diradical will abstract a hydrogen atom from a suitable hydrogen donor to form a ketyl radical.