19788-34-2

Basic information

• Product Name: Benzenamine, N-nitroso-N-propyl-
• CAS NO: 19788-34-2
• Molecular Formula: C9H12N2O
• Molecular Weight: 164.207
• Mol File: 19788-34-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenamine, N-nitroso-N-propyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, N-nitroso-N-propyl-(19788-34-2)
• EPA Substance Registry System: Benzenamine, N-nitroso-N-propyl-(19788-34-2)

Safety Data

• Hazardous Substances Data: 19788-34-2(Hazardous Substances Data)

Upstream product

• 622-80-0 N-propylaniline 
• 13395-54-5 N-methyl-N-n-propylaniline 

Downstream Products

• 109231-01-8 4-nitroso-N-propyl-aniline 
• 74396-53-5 2-(propylamino)benzonitrile 
• 622-80-0 N-propylaniline 

Relevant articles and documents

Cp?Rh(iii) catalyzed: Ortho -halogenation of N -nitrosoanilines by solvent-controlled regioselective C-H functionalization

We present a novel, efficient, and regioselective method for the rhodium-catalyzed direct C-H ortho-halogenation of anilines that involves a removable N-nitroso directing group. This method featured mild reaction conditions, wide substrate scope, good functional group tolerance and satisfactory yields. To maintain the high ortho-regioselectivity and conversion, increasing the steric hindrance of the solvent was critical. Preliminary mechanistic studies suggest that C-H activation may be involved in the rate-determining step.

Unusual Rate-limiting Proton Transfer in the Acid-catalysed Reactions of N-Nitroso Compounds

For both N-methyl-N-nitrosoaniline and N-nitrosodiphenylamine, the catalytic effect of halide ion, thiocyanate ion, and thiourea in the denitrosation reaction in acid solution disappears at high nucleophile concentrations.This suggests a change to an earlier rate-limiting step.The data, including the variation of rate constant with acidity, are quantitatively in accord with a reaction mechanism involving protonation of the nitosamine followed by nucleophilic attack, either stage being rate limiting, depending on the reactivity and concentration of the nucleophile.The kinetic solvent isotope effect kH2O/kD2O decreases from 1.59 at 0.43M-thiourea to 0.71 at 0.015M-thiourea, which is consistent with a change from general acid catalysis at high to specific hydrogen ion catalysis at low .Substituent effects at the amino-nitrogen atom and also in the 4-position of a phenyl substituent are very amall, the largest effect being a three-fold reduction in rate constant effected by a 4-NO2 group.These results are in accord with the known dipolar nature of nitrosamines.There is a close analogy between this system and the acid-catalysed cleavage reaction of carbamate derivatives.A similar mechanism is proposed involving a pre-association of the reactants forming a hydrogen-bonded intermediate.