78521-30-9

Basic information

• Product Name: 1-(pyrrolidinyl)-2,4-dinitronaphthalene
• Synonyms: 1-(pyrrolidinyl)-2,4-dinitronaphthalene
• CAS NO: 78521-30-9
• Molecular Weight: 287.275
• Mol File: 78521-30-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(pyrrolidinyl)-2,4-dinitronaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(pyrrolidinyl)-2,4-dinitronaphthalene(78521-30-9)
• EPA Substance Registry System: 1-(pyrrolidinyl)-2,4-dinitronaphthalene(78521-30-9)

Safety Data

• Hazardous Substances Data: 78521-30-9(Hazardous Substances Data)

Upstream product

• 123-75-1 pyrrolidine 
• 14723-61-6 phenyl 2,4-dinitronaphthyl sulfide 
• 39139-79-2 1-dimethylamino-2,4-dinitronaphthalene 
• 53359-90-3 C₁₇H₂₀N₃O₅^(1-) 
• 15352-94-0 ethyl ether of 2,4-dinitro-1-naphthol 

Downstream Products

• 123-75-1 pyrrolidine 
• 52422-07-8 2,4-dinitro-1-(1-piperidyl)naphthalene 
• 39139-78-1 1-(Methylamino)-2,4-dinitronaphthalene 

Relevant articles and documents

Kinetic Studies of the Reactions of Some Phenyl Aryl Sulfides with Aliphatic Amines in Dimethyl Sulfoxide: the Mechanism of Base Catalysis

The reaction of n-butylamine, pyrrolidine and piperidine with 4'-R-phenyl 2,4,6-trinitrophenyl sulfides (R = H, Me, Br, NO2), 4a-d, result in the rapid formation of ?-adducts by attack at the unsubstituted 3-position; rate and equilibrium data are reported and substituent effects examined. Attack by amine at the 1-position of of 4a-d, phenyl 2,4-dinitronaphthyl sulfide 9, and phenyl 2,6-dinitro-4-trifluoromethyl sulfide 11, results in displacement of the phenylthio group.The substitutions by butylamine show a first order dependence on the amine concentration indicating that nucleophilic attack is rate determining.However the substitutions by pyrrolidine are subject to general base catalysis and it is argued that here the rate limiting step is deprotonation of the initially formed zwitterionic intermediate.

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.