2406-04-4

Basic information

• Product Name: 2,5-Cyclohexadien-1-one, 4-(phenylimino)-
• Synonyms: N-phenyl-p-benzoquinone monoimine;2,5-Cyclohexadien-1-one,4-(phenylimino);N-phenyl-1,4-benzoquinonemonoimine;4-(phenylimino)cyclohexa-2,5-dienone;N-phenyl-1,4-benzoquinone 4-imine;1,4-benzoquinone-4-phenylimine;4-(Phenylimino)-2,5-cyclohexadien-1-one;N-phenyl p-benzoquinone imine
• CAS NO: 2406-04-4
• Molecular Formula: C12H9NO
• Molecular Weight: 183.21
• Mol File: 2406-04-4.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadien-1-one, 4-(phenylimino)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadien-1-one, 4-(phenylimino)-(2406-04-4)
• EPA Substance Registry System: 2,5-Cyclohexadien-1-one, 4-(phenylimino)-(2406-04-4)

Safety Data

• Hazardous Substances Data: 2406-04-4(Hazardous Substances Data)

Usage

General Description

2,5-Cyclohexadien-1-one, 4-(phenylimino)- is a chemical compound that belongs to the class of cyclohexadienones. It is characterized by a cyclohexene ring with a ketone and an imine functional group attached to it. 2,5-Cyclohexadien-1-one, 4-(phenylimino)- is commonly used in organic synthesis for the preparation of various heterocyclic compounds and has been studied for its potential pharmacological and biological activities. Additionally, it is used as a building block for the synthesis of complex organic molecules in medicinal and pharmaceutical research.

Upstream product

• 101-54-2 N-phenylphenylene-1,4-diamine 
• 7732-18-5 water 
• 122-37-2 4-anilinophenol 
• 106-51-4 p-benzoquinone 
• 62-53-3 aniline 
• 60-29-7 diethyl ether 
• 861363-81-7 N,N'-bis-(4-diethylamino-phenyl)-N,N'-diphenyl-hydrazine 
• 1165952-91-9 cyclohexa-1,3-diene 
• 1208-86-2 N-(4-methoxyphenyl)phenylamine 
• 34865-89-9 p-hydroxydiphenylamine radical 
• 134044-81-8 2,5-dichloro-4-hydroxyphenoxyl radical 
• 615-93-0 2,5-Dichloro-1,4-benzoquinone 
• 7646-79-9 cobalt(II) chloride 
• 35548-96-0 N-phenylquinone diimine 

Downstream Products

• 104053-92-1 3-Decylsulfanyl-4-phenylamino-phenol 
• 104053-99-8 2,5-Bis-decylsulfanyl-4-[(E)-phenylimino]-cyclohexa-2,5-dienone 
• 104054-04-8 2,6-Bis-decylsulfanyl-4-phenylimino-cyclohexa-2,5-dienone 
• 104054-07-1 2,3,6-Tris-decylsulfanyl-4-[(E)-phenylimino]-cyclohexa-2,5-dienone 
• 104054-02-6 2-Decylsulfanyl-4-[(Z)-phenylimino]-cyclohexa-2,5-dienone 
• 104054-02-6 2-Decylsulfanyl-4-[(E)-phenylimino]-cyclohexa-2,5-dienone 
• 90712-85-9 2,5-bis(4-chlorophenylamino)-1,4-benzoquinone-4-phenylimine 
• 464-72-2 tetraphenylethane-1,2-diol 
• 122-37-2 4-anilinophenol 
• 106-51-4 p-benzoquinone 
• 615-93-0 2,5-Dichloro-1,4-benzoquinone 
• 134044-81-8 2,5-dichloro-4-hydroxyphenoxyl radical 
• 34865-89-9 p-hydroxydiphenylamine radical 
• 21086-81-7 2,5-Bis(phenylamino)-4-phenylimino-2,5-cyclohexadienone 

Relevant articles and documents

The kinetics of the reversible chain reaction between 2,5-dichloroquinone and 4-hydroxydiphenylamine

The paper presents the results obtained in a study of the kinetics of the reversible chain reaction between 2,5-dichloroquinone and 4-hydroxydiphenylamine (K eq = 3.2). We studied the dependence of the reaction rate on the concentrations of the initiator, initial reagents, and all products. The equations obtained earlier for the rate of reversible chain reactions and the method of equal concentrations suggested in this work were used to estimate the rate constants of most of the reaction mechanism elementary steps from the experimental data. The results obtained were shown to closely agree with and agument the data obtained earlier for the kinetics of the chain reaction between N-phenyl-1,4-benzoquinonemonoimine and 2,5-dichlorohydroquinone. On the whole, all the elementary steps of these two (forward and back) reversible chain reactions were characterized by rate constant values.

Palladium-catalyzed carbonylation of iminoquinones and aryl iodides to access arylp-amino benzoates

A palladium-catalyzed carbonylation of iminoquinones and aryl iodides has been developed for the construction of arylp-amino benzoates. Using benzene-1,3,5-triyl triformate (TFBen) as the CO source, the reaction proceeded well to give various arylp-amino benzoates in good to excellent yields. Additionally, control experiments were conducted to gain more insights into the reaction mechanism.

Pd-Catalyzed Redox-Neutral C-N Coupling Reaction of Iminoquinones with Electron-Deficient Alkenes without External Oxidants: Access of Tertiary (E)-Enamines and Application to the Synthesis of Indoles and Quinolin-4-ones

A novel and efficient reductive N-alkenylation of iminoquinones with electron-deficient olefins has been successfully developed by Pd(II)-catalyzed redox-neutral reactions, which provides a synthesis of tertiary (E)-enamines. We further demonstrate that the tertiary enamines can be converted to multifarious N-heterocyclic compounds, indoles, and quinolones in good yields.

A new method for the synthesis of iminoquinones via DMP-mediated oxidative reaction

Iminoquinones were synthesized by oxidation of primary and secondary amines with hypervalent iodine reagent Dess-Martin periodinane in average to good yields, and possible mechanisms were postulated. This methodology is convenient to establish a library of diversified iminoquinone compounds and has great significance for their potential application in the field of pharmaceuticals.