Benzil

Title: Benzil
CAS Registry Number: 134-81-6
CAS Name: Diphenylethanedione
Additional Names: bibenzoyl; dibenzoyl; diphenylglyoxal; diphenyl-a,b-diketone
Molecular Formula: C14H10O2
Molecular Weight: 210.23
Percent Composition: C 79.98%, H 4.79%, O 15.22%
Literature References: Prepd by the oxidation of benzoin, C6H5CH(OH)COC6H5, with HNO3 or with a copper sulfate-pyridine mixture: Adams, Marvel, Org. Synth. vol. I, p 25 (1921); Clarke, Dreger, ibid. coll. vol. I, 80 (87, 2nd ed); Hatt et al., J. Chem. Soc. 1936, 93; L. F. Fieser, Experiments in Organic Chemistry (Boston, 3rd ed, 1955) p 173; Organic Experiments (Boston, 1964) p 214.
Properties: Yellow prisms (trigonal trapezohedral) from alcohol. d415 1.23. mp 95°. bp760 346-348°; bp12 188°. Absorption spectrum: Hantzsch, Schwiete, Ber. 49, 216 (1916). uv max (ethanol): 260 nm (e 22000). Infrared in chloroform: 5.93; 6.22; 6.85 m. Insol in water; sol in alcohol, ether, chloroform, ethyl acetate, benzene, toluene, nitrobenzene.
Melting point: mp 95°
Boiling point: bp760 346-348°; bp12 188°
Absorption maximum: uv max (ethanol): 260 nm (e 22000)
Density: d415 1.23
Derivative Type: a-Benzilmonoxime
Molecular Formula: C14H11NO2
Molecular Weight: 225.24
Percent Composition: C 74.65%, H 4.92%, N 6.22%, O 14.21%
Properties: Leaflets from 30% alc, mp 137-138°.
Melting point: mp 137-138°
Derivative Type: b-Benzilmonoxime
Molecular Formula: C14H11NO2
Molecular Weight: 225.24
Percent Composition: C 74.65%, H 4.92%, N 6.22%, O 14.21%
Properties: Solvated needles from benzene, when dry mp 113-114°.
Melting point: mp 113-114°
Derivative Type: Disemicarbazone
Molecular Formula: C16H16N6O2
Molecular Weight: 324.34
Percent Composition: C 59.25%, H 4.97%, N 25.91%, O 9.87%
Properties: Leaflets from alc, dec 243-244°.
Use: In organic syntheses.
Benzil Dioxime Benzilic Acid Benzilonium Bromide Benziodarone Benznidazole

Benzil
Benzil
Benzil-from-LT-monoclinic-xtal-CM-3D-balls.png
Benzil-from-LT-monoclinic-xtal-CM-3D-SF.png
Identifiers
CAS number 134-81-6 YesY
PubChem 8651
ChemSpider 8329 YesY
ChEBI CHEBI:51507 YesY
ChEMBL CHEMBL189886 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C14H10O2
Molar mass 210.23 g mol−1
Appearance yellow crystals or powder
Density 1.23 g/cm3, solid (1.255 g/cm3, x-ray)
Melting point 94-96 °C, 201.2–204.8 °F, 367.15-369.15 K
Boiling point 346–348 °C, 654.8–658.4 °F, 619–621 K
Solubility in water insoluble
Solubility in benzene soluble
Structure
Crystal structure P31,221[1]
Dipole moment 3.8 D[2]
Hazards
Main hazards Irritant
NFPA 704
NFPA 704.svg
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2
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Related compounds
Related diketones biacetyl
Related compounds benzophenone
glyoxal
bibenzil
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Benzil (systematically known as 1,2-diphenylethane-1,2-dione) is the organic compound with the formula (C6H5CO)2, generally abbreviated (PhCO)2. This yellow solid is one of the most common diketones. Its main use is as a photoinitiator in polymer chemistry.[3]