58784-38-6

Basic information

• Product Name: 4-nitrophenylketene
• Synonyms: 4-nitrophenylketene
• CAS NO: 58784-38-6
• Molecular Weight: 163.133
• Mol File: 58784-38-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-nitrophenylketene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrophenylketene(58784-38-6)
• EPA Substance Registry System: 4-nitrophenylketene(58784-38-6)

Safety Data

• Hazardous Substances Data: 58784-38-6(Hazardous Substances Data)

Upstream product

• 3282-33-5 1-(4-chlorophenyl)-2-diazoethanone 
• 4203-31-0 2-diazo-1-(4-nitrophenyl)ethanone 
• 108099-76-9 2,4-dinitrophenyl 4-nitrophenylacetate 
• 35665-94-2 p-nitrophenyl p-nitrophenylacetate 

Downstream Products

• 50507-86-3 Diethylamide of p-nitrophenylacetic acid 
• 1497283-55-2 C₁₂H₁₆N₂O₃ 
• 104-03-0 4-nitrobenzeneacetic acid 
• 105625-84-1 3-[(E)-3-(4-Nitro-phenyl)-acryloyl]-5-[1-(4-nitro-phenyl)-meth-(E)-ylidene]-2-phenyl-3,5-dihydro-imidazol-4-one 
• 105625-86-3 5-[1-(4-Hydroxy-phenyl)-meth-(E)-ylidene]-3-[(E)-3-(4-nitro-phenyl)-acryloyl]-2-phenyl-3,5-dihydro-imidazol-4-one 
• 105625-82-9 3-[(E)-3-(4-Nitro-phenyl)-acryloyl]-2-phenyl-5-[1-phenyl-meth-(E)-ylidene]-3,5-dihydro-imidazol-4-one 
• 33703-64-9 1-(p-nitrophenyl)-2-hydroxycyclobutene-3,4-dione 

Relevant articles and documents

Ketene-forming eliminations from aryl phenylacetates promoted by R2NH/R2NH2+ in aqueous MeCN. Mechanistic borderline between E2 and E1cb

Elimination reactions of 2-X-4-NO2C6H3CH2C(O) OC6H3-2-Y-4-NO2 [X = H (1), NO2 (2)] promoted by R2NH/R2NH2+ in 70 mol % MeCN(aq) have been studied kinetically. The base-promoted eliminations from 1 proceeded by the E2 mechanism when Y = Cl, CF3, and NO2. The mechanism changed to the competing E2 and E1cb mechanisms by the poorer leaving groups (Y = H, OMe) and to the E1cb extreme by the strongly electron-withdrawing β-aryl group (2, X = NO2). The values of β = 0.14 and |β1g| = 0.10-0.21 calculated for elimination from 1 (Y = NO2) indicate a reactant-like transition state with small extents of proton transfer and Cα-OAr bond cleavage. The extent of proton transfer increased with a poorer leaving group, and the degree of leaving group bond cleavage increased with a weaker base. Also, the changes in the k1 and k-1/k2 values with the reactant structure variation are consistent with the E1cb mechanism. From these results, a plausible pathway of the change of the mechanism from E2 to the E1cb extreme is proposed.

Aminoxyl radical addition to arylketenes

Kinetic studies of the addition of the aminoxyl radical TEMPO (2,2,6,6-tetramethylpiperidinylaminoxyl, TO) to the 4-substituted phenylketenes 8 (4-RC6H4CH=C=O, R=NO2, CN, Cl, H, CH 3, CH3O) and to 3-p

Reactions of aryl phenylacetates with secondary amines in MeCN. Structure-reactivity relationship in the ketene-forming eliminations and concurrent E2 and E1cb mechanisms

Elimination reactions of aryl esters of arylacetic acids 1 and 2 promoted by R2NH in MeCN have been investigated kinetically. The reactions are second-order and exhibit β = 0.44-0.84, β(lg) = 0.41-0.50, and ρ(H) = 2.0-3.6. Bronsted β and β(lg) decrease with the electron-withdrawing ability of the β-aryl substituent. Hammett ρ(H) values remain nearly the same, but the β(lg) value increases as the base strength becomes weaker. Both ρ(H) and β decrease with the change of the leaving group from 4-nitrophenoxide to 2,4-dinitrophenoxide. The results are consistent with an E2 mechanism and a reaction coordinate with a large horizontal component corresponding to proton transfer. When the base-solvent system is changed from R2NH-MeCN to R2NH/R2NH2+-70 mol% MeCN(aq), the Bronsted β, ρ(H), and β(lg) decrease. Finally, the ketene-forming elimination reactions from p-nitrophenyl p-nitrophenylacetate promoted by R2NH/R2NH2+ buffers in 70 mol% MeCN(aq) have been shown to proceed by concurrent E2 and E1cb mechanisms.