32352-96-8

Basic information

• Product Name: 4-nitro-N-nitrosoaniline
• CAS NO: 32352-96-8
• Molecular Formula: C₆H₄N₃O₃*Na
• Molecular Weight: 167.1222
• Mol File: 32352-96-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 290.3°C at 760 mmHg
• Flash Point: 129.4°C
• Density: 1.48g/cm³
• Vapor Pressure: 0.00209mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: 4-nitro-N-nitrosoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitro-N-nitrosoaniline(32352-96-8)
• EPA Substance Registry System: 4-nitro-N-nitrosoaniline(32352-96-8)

Safety Data

• Hazardous Substances Data: 32352-96-8(Hazardous Substances Data)

Upstream product

• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 

Downstream Products

• 148516-30-7 2-(4-nitro-phenylhydrazono)-3-oxo-glutaric acid diethyl ester 
• 85182-66-7 3-(4-nitro-phenylazomethylene)-4-phenyl-3,4-dihydro-benzo[f]quinoline 
• 85182-67-8 3-(4-nitro-phenylazomethylene)-4-p-tolyl-3,4-dihydro-benzo[f]quinoline 
• 102468-31-5 2-(4-nitro-phenylazomethylene)-1-phenyl-1,2-dihydro-quinoline 
• 18795-00-1 ethyl 2-((4-nitrophenyl)hydrazono)-3-oxobutanoate 
• 77083-58-0 2-(4-nitro-phenylhydrazono)-3-oxo-3-phenyl-propionic acid ethyl ester 
• 101445-29-8 1-methyl-2-(4-nitro-phenylazomethylene)-1,2-dihydro-quinoline 
• 102241-78-1 10-methyl-9-(4-nitro-phenylazomethylene)-9,10-dihydro-acridine 
• 20020-13-7 N,4-dinitroaniline 
• 50711-98-3 pentane-2,3,4-trione-3-(4-nitro-phenylhydrazone) 
• 6410-10-2 para red 
• 74-39-5 4-(p-nitrophenylazo)resorcinol 
• 61889-45-0 3-bromo-7-methyl-6-(4-nitro-phenylazomethylene)-6,7-dihydro-isothiazolo[5,4-b]pyridine 
• 61889-44-9 3-bromo-4,7-dimethyl-6-(4-nitro-phenylazomethylene)-6,7-dihydro-isothiazolo[5,4-b]pyridine 

Relevant articles and documents

Base-Free Cross-Couplings of Aryl Diazonium Salts in Methanol: PdII–Alkoxy as Reactivity-Controlling Intermediate

Pd-catalyzed cross-coupling reactions of aryl diazonium salts are generally assumed to proceed via cationic PdII intermediates which in turn would be highly reactive in the subsequent transmetalation step. Contrary to this belief, we herein report our observation and rationalization of opposing reactivities of ArN2+ in Suzuki (=effective) and Stille (=ineffective) cross-couplings in MeOH. Our systematic experimental and computational studies on the roles of transmetalating agent, solvent, base and the likely involvement of in situ formed diazoether derivatives challenge the currently accepted mechanism. Our data suggest that the observed solvent dichotomy is primarily due to PdII-methoxy intermediates being formed, which are unreactive with arylstannanes, but highly reactive with arylboronic acids, complementing the Suzuki “Pd-oxy” mechanism with the direct demonstration of transmetalation of a PdII-alkoxy complex. Lewis acids were found to circumvent this reactivity divergence, promoting efficient couplings regardless of the employed conditions or coupling partners.