927896-38-6

Basic information

• Product Name: (E)-1-(2-iodo-4-methylphenyl)-2-phenyldiazene
• Synonyms: (E)-1-(2-iodo-4-methylphenyl)-2-phenyldiazene
• CAS NO: 927896-38-6
• Molecular Weight: 322.148
• Mol File: 927896-38-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (E)-1-(2-iodo-4-methylphenyl)-2-phenyldiazene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(2-iodo-4-methylphenyl)-2-phenyldiazene(927896-38-6)
• EPA Substance Registry System: (E)-1-(2-iodo-4-methylphenyl)-2-phenyldiazene(927896-38-6)

Safety Data

• Hazardous Substances Data: 927896-38-6(Hazardous Substances Data)

Upstream product

• 29289-13-2 2-iodo-4-methylaniline 
• 586-96-9 Nitrosobenzene 
• 6720-39-4 trans-phenyl-p-tolyl-diazene 

Downstream Products

• 1374253-94-7 C₂₅H₂₁N₂PS 
• 1026815-75-7 5-methyl-2-phenyl-3-triethylsilanyloxymethyl-2H-indazole 
• 1026526-49-7 (2-ethynyl-4-methyl-phenyl)-phenyl-diazene 

Relevant articles and documents

Experimental and theoretical investigation of the coarctate cyclization of (2-ethynylphenyl)phenyldiazenes

A new route to substituted 2-phenyl-2H-indazoles through the cyclization of (2-ethynylphenyl)-phenyldiazenes is presented. A coarctate reaction pathway forms the isoindazole carbene under neutral conditions, at moderate temperatures, and without the requirement of a carbene stabilizer. A wide variety of previously unknown diazene precursors was synthesized and cyclized. Trapping of the carbene with a silyl alcohol followed by deprotection affords the 3-hydroxymethyl-2-phenyl-2H-indazoles in good overall yield. The free carbene could also be trapped as a [2 + 1] cycloadduct with 2,3-dimethyl-2- butene.

Control of the equilibrium between 2-phosphinoazobenzenes and inner phosphonium salts by heat, solvent, acid, and photoirradiation

Several 2-phosphinoazobenzenes, which are in equilibrium with inner phosphonium salts, were synthesized. Effects of substituents, solvents, and acidic additives on their equilibria are described. Thermodynamic parameters of the equilibria in various solvents suggest that the acceptor character of the solvents is mainly responsible for the solvent effects. Addition of phenols changed the equilibria depending on their acidity. Substituents at the 4- and 4′-positions of the azobenzene also affected the equilibrium constants, which shifted the equilibrium toward the phosphonium salt in the order of their electron-withdrawing ability. Photoisomerization of the 2-phosphinoazobenzenes bearing electron-donating substituents at the 4- and 4′-positions, which shifted the equilibrium toward the 2-phosphinoazobenzene, proceeded successfully. While the phosphonium salt in equilibrium with the (E)-isomer of the 2-phosphinoazobenzene was protonated by perchlorophenol, the (Z)-isomer did not react with a proton source because it could not take on the form of an inner phosphonium salt. Thus, the properties and reactivity of the inner phosphonium salts in equilibrium with the phosphines can be successfully controlled by photoirradiation.