Phenylazo -diphenylamine

Other Names Diphenylamine, 4-(phenylazo)- 4-(Phenylamino)azobenzene 4- (Phenylazo)dip henylamine 4-Anilinoazobenzene 4- Phenazodiphenylamine Af-Phenyl-4-(phenylazo)aniline N- Phenyl-4-(phenylazo)benzenamine Af-Phenyl-4-aminoazobenzene NSC 74774 CA Index Name Benzenamine, Af-phenyl-4-(phenylazo)-CAS Registry Number 101-75-7 Merck Index Number Not listed Chemical Structure 

Chemical/Dye Class Azo Molecular Formula C18H15N3 Molecular Weight 273.33 pH Range 1.2-2.5 

Solubility Insoluble in water soluble in ethanol, methanol UV-Visible (X ) 411 nm, 272 nm Melting Point 89-91°C 

Boiling Point (Calcd.) 451.7 28.0°C Pressure 760 Torr Synthesis Synthetic methodsi-i  

Major Applications Display device,nonlinear optial (NLO) material, photoresists, printing plates, 1 - lithographic plates, photosensitive materials,photography,2o markers Safety/Toxicity Oral toxicity  

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Nucleophilic displacements on unsubstituted aromatics usually do not occur since H is not a good leaving group. However, an example of nucleophilic aromatic substitution of hydrogen (NASH) has been reported on reacting aniline and azobenzene in the presence of base under aerobic conditions to generate 4-(phenylazo)diphenylamine, 9 (equation 13)115. 

Spiro-ADA 55, which contains four phenylazodiphenylamine groups, was synthesized by Hartwig-Buchwald coupling of 4-(phenylazo)diphenylamine and 2,2, 7,7 -tetrabromo-9,9 -spirobifluorene (14) in 89% yield [98]. 

Preparation of TMPMgCI LiCI (64) A dried and argon-flushed 2 L 5c/i/e -flask, equipped with a magnetic stirring bar and rubber septum, was charged with /-PrMgCl LiCl (1.31 M in THF, 850 mL, 1.11 mol). Then, 2,2,6,6-tetramethylpiperidine (161 g, 194 mL, 1.14 mol, 1.02 equiv.) was added at once and the mixture was stirred until gas evolution ceases (48 h). Titration with benzoic acid using 4-(phenylazo)diphenylamine as indicator prior to use showed a concentration of 1.15 M. 

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