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.

Kinetics of Reactions of Cyclic Secondary Amines with 2,4-Dinitro-1-naphthyl Ethyl Ether in Dimethyl Sulfoxide Solution. Spectacular Difference between the Behavior of Pyrrolidine and Piperidine

The reactions named in the title, which form N-(2,4-dinitro-1-naphthyl) derivatives of these heterocyclic amines, occur in two distinct stages.In stage I, the spectrum of a ?-adduct intermediate develops at a rate which is measurable in a stopped flow apparatus; in stage II, it decays at a slower and easily measurable rate.The kinetics of both stage I and stage II have been studied.Pyrrolidine and piperidine are similar in their stage I behavior, but reactivity in stage II is about 11000 times greater in the pyrrolidine system.This huge difference between systems apparently so similar is judged to arise from steric interactions forced by differences in conformation between the amino moieties in the intermediate ? adducts as they release the nucleofuge.It calls into question the rate-limiting proton transfer interpretation of base catalysis in analogous aminodephenoxylation reactions in protic solvents.