7775-81-7

Basic information

• Product Name: Diazene, bis[4-(1,1-dimethylethyl)phenyl]-
• CAS NO: 7775-81-7
• Molecular Formula: C20H26N2
• Molecular Weight: 294.44
• Mol File: 7775-81-7.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Diazene, bis[4-(1,1-dimethylethyl)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Diazene, bis[4-(1,1-dimethylethyl)phenyl]-(7775-81-7)
• EPA Substance Registry System: Diazene, bis[4-(1,1-dimethylethyl)phenyl]-(7775-81-7)

Safety Data

• Hazardous Substances Data: 7775-81-7(Hazardous Substances Data)

Upstream product

• 769-92-6 4-tert-Butylaniline 
• 7775-78-2 1,2-di(p-tert-butylphenyl)hydrazine 
• 98-80-6 phenylboronic acid 
• 18522-89-9 1-azido-4-tert-butylbenzene 
• 214360-66-4 2-(4-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 544-16-1 n-Butyl nitrite 
• 3282-56-2 4-tert-butylnitrobenzene 

Downstream Products

• 6479-87-4 2-(tert-butyl)phenazine 
• 17082-79-0 1.2.4.5-Tetrakis-<4-tert.-butyl-phenyl>-3.3.6.6-tetraphenyl-1.2.4.5-tetraaza-3.6-disila-cyclohexan 

Relevant articles and documents

Azo synthesis meets molecular iodine catalysis

A metal-free synthetic protocol for azo compound formation by the direct oxidation of hydrazine HN-NH bonds to azo group functionality catalyzed by molecular iodine is disclosed. The strengths of this reactivity include rapid reaction times, low catalyst loadings, use of ambient dioxygen as a stoichiometric oxidant, and ease of experimental set-up and azo product isolation. Mechanistic studies and density functional theory computations offering insight into this reactivity, as well as the events leading to azo group formation are presented. Collectively, this study expands the potential of main-group element iodine as an inexpensive catalyst, while delivering a useful transformation for forming azo compounds.

Photocatalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

Visible light mediated oxidative dehydrogenation of hydrazobenzenes under an ambient atmosphere using an organic dye as a photocatalyst was reported for the first time. The reaction provides an environmentally benign method for the preparation of azobenzenes in excellent yields with good functional group tolerance.

Chan-Evans-Lam Couplings with Copper Iminoarylsulfonate Complexes: Scope and Mechanism

Copper(II) pyridyliminoarylsulfonate complexes with chloride or triflate counteranions were employed in Chan-Evans-Lam (CEL) couplings of N-nucleophiles and arylboronic acids. The complexes avoided typical side reactions in CEL couplings, and an excess of boronic acid was not required. Water was tolerated, and addition of neither base nor other additives was necessary. Primary amines, acyclic and cyclic secondary amines, anilines, aminophenol, imidazole, pyrazole, and phenyltetrazole can be quantitatively arylated at either 25 or 50 °C with 2.5 mol % of the catalyst. Reaction kinetics were investigated in detail. Kinetic and spectroscopic studies provide evidence for the formation of unproductive copper-substrate complexes. Formation of an aniline-phenylboronic acid adduct was responsible for the zero-order dependence of reaction rates on phenylboronic acid concentration. Kinetic evidence indicates that the order of reaction steps is transmetalation, nucleophile coordination, and oxidation. Couplings performed poorly with electron-deficient arylboronic acids, due to a slower Cu(II)/Cu(III) oxidation in the catalytic cycle. Photoredox catalysis partially resolved this problem, but addition of copper acetate as an external oxidant proved to be more efficient.