143726-74-3

Basic information

• Product Name: 2,5-Cyclohexadien-1-imine, 2,4,6-tris(1,1-dimethylethyl)-4-[(1,1-dimethylethyl)dioxy]-
• CAS NO: 143726-74-3
• Molecular Formula: C22H39NO2
• Molecular Weight: 349.557
• Mol File: 143726-74-3.mol

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadien-1-imine, 2,4,6-tris(1,1-dimethylethyl)-4-[(1,1-dimethylethyl)dioxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadien-1-imine, 2,4,6-tris(1,1-dimethylethyl)-4-[(1,1-dimethylethyl)dioxy]-(143726-74-3)
• EPA Substance Registry System: 2,5-Cyclohexadien-1-imine, 2,4,6-tris(1,1-dimethylethyl)-4-[(1,1-dimethylethyl)dioxy]-(143726-74-3)

Safety Data

• Hazardous Substances Data: 143726-74-3(Hazardous Substances Data)

Upstream product

• 961-38-6 2,4,6-Tri-tert-butylaniline 
• 75-91-2 tert.-butylhydroperoxide 

Relevant articles and documents

Catalytic oxidation of a trialkyl-substituted phenol and aniline with biomimetic schiff base complexes

The catalytic oxidation of 2,4,6-tri-tert-butylphenol and 2,4,6-tri-tert-butylaniline with molecular oxygen and tert-butylhydroperoxide was investigated using biomimetic Mn-, Fe- and Co-complexes as catalysts. The catalytic activity and product distribution were determined and compared with those observed in the reactions of the well-known Co(salen) complex.

Cobalt schiff base complex-catalyzed oxidation of anilines with tert-butyl hydroperoxide

Cobalt Schiff base complexes [Co(SB)] catalyze the oxidation of anilines (1) with tert-butyl hydroperoxide to give nitrobenzenes 2 and 4-(tert-butylperoxy)-2,5-cyclohexadien-1-imine derivatives 3 in yield distributions depending on the substitution mode of the substrate. 4-Alkyl- and 4-aryl-2,6-di-tert-butylanilines gave mixtures of 2 and 3, where the higher the bulkiness of the 4-substituent, the higher the yield of 2. With 2,4,6-trimethylaniline, the ratio of oxidations of the nitrogen and C-4 atoms was almost the same; but a hydrolyzed product 5 of the imine was obtained. 2,4,6-Triphenylaniline gave only 2. Nitrobenzene derivatives were also obtained from 2,6-dialkylanilines and 4-substituted anilines. The catalytic activity of Co(SB) depended on the nature of the SB ligand: the formal potential E° and steric factors seem to affect the reaction rate. Kinetic studies showed that the key step may involve hydrogen abstraction from the aniline, presumably by t-BuO? generated from homolytic decomposition of initially formed CoIII(SB)(OO-t-Bu). A precursor of 2 was found to be the nitrosobenzene derivative.

Co(salen) catalyzed oxidation of 2,4,6-trisubstituted anilines with tert-butylhydroperoxide

Co(salen) catalyzed oxidation of 2,4,6-trisubstituted (preferentially 2,6-di-tert-butylated) anilines with tert-butylhydroperoxide gives 4-tert-butylperoxy-2,5-cyclohexadien-1-imine and nitrobenzene derivatives. The relative ratio of the products depends on the nature of the substituents in the substrate.