52422-07-8

Basic information

• Product Name: Piperidine, 1-(2,4-dinitro-1-naphthalenyl)-
• CAS NO: 52422-07-8
• Molecular Formula: C15H15N3O4
• Molecular Weight: 301.302
• Mol File: 52422-07-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Piperidine, 1-(2,4-dinitro-1-naphthalenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine, 1-(2,4-dinitro-1-naphthalenyl)-(52422-07-8)
• EPA Substance Registry System: Piperidine, 1-(2,4-dinitro-1-naphthalenyl)-(52422-07-8)

Safety Data

• Hazardous Substances Data: 52422-07-8(Hazardous Substances Data)

Upstream product

• 110-89-4 piperidine 
• 78521-30-9 1-(pyrrolidinyl)-2,4-dinitronaphthalene 
• 39139-79-2 1-dimethylamino-2,4-dinitronaphthalene 
• 53359-90-3 C₁₇H₂₀N₃O₅^(1-) 
• 14723-61-6 phenyl 2,4-dinitronaphthyl sulfide 
• 15352-94-0 ethyl ether of 2,4-dinitro-1-naphthol 

Downstream Products

• 110-89-4 piperidine 
• 39139-78-1 1-(Methylamino)-2,4-dinitronaphthalene 

Relevant articles and documents

Sopped-Flow Kinetics of 1-Ethoxy-2,4-dinitronaphthalene with Pyrrolidine and Piperidine in Dimethyl Sulfoxide Solution

The reaction of 1-ethoxy-2,4-dinitronaphthalene (1) with pyrrolidine or piperidine in dimethyl sulfoxide occured in two stages (Stages I and II).In the stage I, a ?-adduct forms at such a rate as is measured by a stopped-flow technique, and in the stage II it decays at a slower and spectrophotometrically measurable rate.The pyrrolidine system is more reactive than the piperidine system in the stages I and II, with the former reactivity in the stage II being ca. 11000 times higher than the latter.This huge difference was found by NMR evidence to stem from the structure of transition state in the stage II.Further, the activation parameters were determined, which corresponded to such difference in reactivity very well.

Aromatic Nucleophilic Substitution Reactions of 1-Dialkylamino-2,4-dinitronaphthalene with Primary or Secondary Amines in Organic Solvents: Facile Amine-Amine Exchange

The dialkylamino group, (e.g., dimethyl-, diethyl-, and N-n-butyl-N-methylamino, piperidino, and pyrrolidino) of 1-dialkylamino-2,4-dinitronaphthalenes is rapidly replaced by primary amines, particulary in dimethyl sulphoxide; however, substitution does not occur for secondary amines except in the case of pyrrolidine.

Reactions of Secondary amines with Their N-(2,4-Dinitro-1-naphthyl)Derivatives To Form Jackson-Meisenheimer Adducts. Substantial Difference in Reaction Rates between Pyrrolidine and Piperidine

Pyrrolidine, piperidine, and butylmethylamine react with their respective N-(2,4-dinitro-1-naphthyl) derivatives to form ? adducts as through the respective amide ions had attached at the 1 position.These reactions occur in dimethyl sulfoxide solution and proceed to a state of equilibrium.For the pyrrolidine and butylmethylamine reactions, equilibrium constants as well as rate constants both foward and reverse have been measured.Although two amine molecules are required to form the ? adduct, one to supply an amino moiety and the other to receive a proton, the forward reaction is only first order in amine; therefore, amine attack is not base catalyzed.Piperidine reacts so much slower than pyrrolidine, roughly 1/400th as fast, that rate and equilibrium measurements were inconvenient.The low reactivity of the piperidine system is ascribed to stereoelectronic/conformational/steric problems in the piperidino moiety of N-(2,4-dinitro-1-naphthyl)piperidine as it enters the transition state.