525-06-4

Basic information

• Product Name: DIPHENYLKETENE
• Synonyms: DIPHENYLKETENE;2,2-Diphenylethylenone;Ethenone,diphenyl-;Diphenylethenone;2,2-Diphenylethenone;Ethenone, 2,2-diphenyl-;2-diphenylethenone
• CAS NO: 525-06-4
• Molecular Formula: C₁₄H₁₀O
• Molecular Weight: 194.2286
• Mol File: 525-06-4.mol
• Article Data: 45

Chemical Properties

• Melting Point: 201 °C(Solv: acetic acid (64-19-7))
• Boiling Point: bp760 265-270° (dec); bp12 146°; bp3.5 119-121°
• Flash Point: 106.4°C
• Appearance: /
• Density: d413.7 1.1107
• Vapor Pressure: 0.00812mmHg at 25°C
• Refractive Index: nD14.1 1.615
• CAS DataBase Reference: DIPHENYLKETENE(CAS DataBase Reference)
• NIST Chemistry Reference: DIPHENYLKETENE(525-06-4)
• EPA Substance Registry System: DIPHENYLKETENE(525-06-4)

Safety Data

• Hazardous Substances Data: 525-06-4(Hazardous Substances Data)

Usage

Chemical Description

Diphenylketene is an organic compound with two phenyl groups and a ketene functional group.

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 4604, 1971 DOI: 10.1021/ja00747a050Organic Syntheses, Coll. Vol. 3, p. 356, 1955

InChI:InChI=1/C14H10O/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H

Upstream product

• 4173-55-1 8,8-diphenyl-bicyclo[4.2.0]octan-7-one 
• 3469-15-6 Diphenylketene dimer 
• 858852-64-9 N-diphenylacetyl-phthalimide 
• 1070988-51-0 3-(4-Methoxy-phenyl)-2,2-diphenyl-cyclobutanon 
• 3469-17-8 2-diazo-1,2-diphenylethan-1-one 
• 71-43-2 benzene 
• 73388-91-7 4-allylthio-3,3,4-triphenyl-2-thietanone 
• 17397-37-4 α,α-bromodiphenylacetyl bromide 
• 79457-95-7 2-(Diphenylmethylen)-7a-ethoxytetrahydro-5-oxo-6,6-diphenyloxazolo<2,3-b><1,3,4>oxadiazol-3-carbonsaeure-ethylester 
• 1871-76-7 diphenylacetic acid chloride 
• 74487-99-3 benzoylphenylmethylene 
• 201230-82-2 carbon monoxide 
• 96010-02-5 benzophenone tosylhydrasone sodium salt 
• 94258-23-8 N-(2-pyridyl)diphenylacetamide 

Downstream Products

• 3626-07-1 diphenyl-acetic acid-(2-piperidino-ethyl ester) 
• 105209-47-0 8a-methyl-6,6,8,8-tetraphenyl-tetrahydro-thiazolo[3,2-a]pyridine-5,7-dione 
• 93331-11-4 N-(4,5-dihydro-thiazol-2-yl)-2,2-diphenyl-acetamide 
• 124483-50-7 diphenyl-thioacetic acid S-(7-oxo-6,6-diphenyl-4-thia-1-aza-bicyclo[3.2.0]hept-5-yl ester) 
• 55860-91-8 (2E)-1,1,2,4-tetraphenyl-1,3-butadiene 
• 3718-76-1 diphenyl-acetic acid-(4-oxo-1,3,3-triphenyl-3,4-dihydro-[2]naphthyl ester) 
• 68578-76-7 4-(2,2-diphenyl-vinyl)-N,N-dimethyl-aniline 
• 59260-77-4 1,1-bis(4-dimethylaminophenyl)-2,2-diphenylethene 
• 57301-86-7 1-benzhydrylidene-4,4-diphenyl-4,4a-dihydro-[1,3]oxazino[3,4-a]quinolin-3-one 
• 112222-85-2 N-benzoyl-O-diphenylacetyl-hydroxylamine 
• 102594-20-7 5,6,6-triphenyl-4-thia-1-aza-bicyclo[3.2.0]heptan-7-one 
• 116028-06-9 1-(4-methoxy-phenyl)-3,3,4-triphenyl-azetidin-2-one 
• 4107-01-1 N-(p-tolyl)diphenylacetamide 
• 18648-74-3 2,2-diphenyl-1-(4-methoxyphenyl)ethylene 

Relevant articles and documents

Synthesis of 3-alkylseleno-2-cylcobutenone via [2+2] cycloaddition reaction of alkyneselenolate with diphenylketene

3-Alkylseleno-2-cyclobutenones were synthesized by reaction of alkyneselenolate with diphenylketene via [2+2] cycloaddition. The complete structure of the 2-cyclobutenone was determined by X-ray diffraction.

Synthesis and time resolved infrared analysis of photochemical oxiranyl carbene and diphenyl ketene precursors

Synthesis of a nonnitrogenous phenanthrene-based precursor of oxiranyl carbene yielded a photochemical source for diphenyl ketene after an in situ intramolecular rearrangement. The initial carbene precursor targeted rearranged from a putative spiro-oxiranyl intermediate to a cyclobutanone. Photolysis of the phenanthrene–cyclobutanone generated an infrared signal centered at 2100?cm?1consistent with diphenyl ketene formation. Time-resolved infrared spectroscopy followed the reaction progress and measured bimolecular rate constants (kobs?=?9.1?×?106?M?1?s?1; butyl amine) consistent with diphenyl ketene formation. Quenching experiments combined with Stern–Volmer kinetics suggests a radical pathway is likely involved in the formation of diphenyl ketene from the phenanthrene-based precursor. The generality of the rearrangement is also discussed.

Coordination behaviors of diphenylketene adsorbed in the nanocages of zeolite NaY and AgY

We investigated in detail how polar cumulene molecules like diphenylketene were accommodated in faujasite zeolite pores based on 13C CP/MAS and DD/MAS NMR analyses as well as quantum chemical calculations after adsorbing the molecule into the zeolite NaY or AgY having “hard” sodium ions or “soft” silver ions. Since the diphenylketene has such a specific structure that a carbonyl group (a hard base) is accumulated by a carbon-carbon double bond (a soft π base), which is conjugated with two benzene rings (soft π bases), it is possible for the diphenylketene to adopt multicoordination modes to different metal ions in the zeolite. Compared with the coordination modes of benzophenone and 1,1-diphenylethene adsorbed in the NaY and AgY, those of diphenylketene were identified, and specific coordination behaviors in the zeolite’s supercages were classified depending on the hard or soft metal characters: The C=O and phenyl coordination modes to Na+ in NaY prevail, while the C=C and phenyl coordination to Ag+ in AgY is favored. We also unveiled the difference in the molecular mobility depending on the types of cations in the zeolite by comparing the 13C CP/MAS and DD/MAS NMR spectra.

Thermal [2+2]-cycloadditions of diphenylketene with aryl- and hetaryl-substituted thioketones

The reaction of diphenylketene (1) with aryl- and hetaryl-substituted thioketones (2) gave the corresponding 3,3,4,4-tetraarylthietan-2-ones (3) in good yields. Remarkably, the reactions with bis-hetaryl-substituted thioketones occurred significantly faster compared with those involving the bis-aryl-substituted thioketones. The structure of compound 3c has been established by X-ray crystallography.