DIPHENYLKETENE Chemical Properties

Melting point:

201 °C(Solv: acetic acid (64-19-7))

Boiling point:

bp760 265-270° (dec); bp12 146°; bp3.5 119-121°

Density 

d413.7 1.1107

refractive index 

nD14.1 1.615

solubility 

sol benzene, THF

NIST Chemistry Reference

Ethenone, 2,2-diphenyl-(525-06-4)

DIPHENYLKETENE Usage And Synthesis

Uses

Diphenylketene is used for acylation of carboxylic acids to give mixed anhydrides; cycloaddition with a variety of unsaturated compounds; synthetic source of diphenylallenes.

Preparation

Preparative Methods of Diphenylketene: originally prepared by zinc reduction of α-chlorodiphenylacetyl chloride; oxidation of benzil monohydrazone with yellow Mercury(II) Oxide followed by thermal rearrangement of the α-diazo ketone; dehydrohalogenation of diphenylacetyl chloride with Triethylamine; debromination of α- bromodiphenylacetyl bromide by the action of Triphenylphosphine.

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 4604, 1971 DOI: 10.1021/ja00747a050
Organic Syntheses, Coll. Vol. 3, p. 356, 1955

storage

Diphenylketene stored in a tightly stoppered bottle at 0 °C is stable for several weeks. Trace amounts of hydroquinone and storage under nitrogen inhibit polymerization and lead to increased stability. Given the reactivity of diphenylketene with amino acids, care should be taken to avoid skin contact.

DIPHENYLKETENE(525-06-4)Related Product Information

• DIPHENYLKETENE
• ketene
• Benzil
• 1,4-Benzoquinone
• Dimethylketene