52010-83-0

Basic information

• Product Name: Piperidine, 1-[(4-nitrophenyl)azo]-
• CAS NO: 52010-83-0
• Molecular Formula: C11H14N4O2
• Molecular Weight: 234.258
• Mol File: 52010-83-0.mol

Chemical Properties

• CAS DataBase Reference: Piperidine, 1-[(4-nitrophenyl)azo]-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine, 1-[(4-nitrophenyl)azo]-(52010-83-0)
• EPA Substance Registry System: Piperidine, 1-[(4-nitrophenyl)azo]-(52010-83-0)

Safety Data

• Hazardous Substances Data: 52010-83-0(Hazardous Substances Data)

Upstream product

• 110-89-4 piperidine 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 1947-33-7 4-nitrobenzenediazonium 4-methylbenzenesulfonate 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 92-93-3 1-phenyl-4-nitrobenzene 
• 110-89-4 piperidine 
• 100-00-5 4-chlorobenzonitrile 
• 619-72-7 4-nitrobenzonitrile 
• 636-98-6 p-nitrobenzene iodide 
• 57103-78-3 4,5-dimethyl-1-(4-nitro-phenyl)-1,6-dihydro-pyridazine 
• 99366-04-8 (E)-1-(2-(4-nitrophenyl)diazen-1-yl)naphthalen-2-ol 

Relevant articles and documents

Protein Modification via Mild Photochemical Isomerization of Triazenes to Release Aryl Diazonium Ions

This work describes the development of phenyl diazenyl piperidine triazene derivatives that can be activated to release aryl diazonium ions for labeling of proteins using light. These probes show marked bench stability at room temperature and can be photoisomerized via low-intensity UVA irradiation at physiological pH. Upon isomerization, the triazenes are rendered more basic and readily protonate to release reactive aryl diazonium ions. It was discovered that the intensity and duration of the UV light was essential to the observed diazonium ion reactivity in competition with the traditionally observed photolytic radical pathways. The combination of their synthetic efficiency coupled with their overall stability makes triazenes an attractive candidate for use in bioconjugation applications. Bioorthogonal handles on the triazenes are used to demonstrate the ease by which proteins can be modified.

Comparison of the Thermal Stabilities of Diazonium Salts and Their Corresponding Triazenes

A range of diazonium salts and their corresponding triazenes have been prepared in order to directly compare their relative thermal stabilities (via initial decomposition temperature) from differential scanning calorimetry (DSC) data. A structure-stability relationship has been explored to investigate trends in stability, depending on the aromatic substituent and the structure of the secondary amine component of the diazonium salts and triazenes. All of the triazenes investigated show significantly greater stability (many are stable above 200 °C) compared with the corresponding diazonium salts, which show varying stabilities.

Synthesis of triazenes of n-heterocycles mediated by resin immobilized diazonium ions

Diazonium ions were prepared from aromatic amines and immobilized in cation exchange resin support and used for the synthesis of triazenes of piperidine and morpholine in a solid phase synthesis. Immobilization is an excellent technique for the stabilization of diazonium ions and can be preserved in the solid state. Using resin immobilized diazonium ions, triazene synthesis is carried out in the absence of acids thereby increasing the yield of the product and simplifying work up.

Synthesis of triazenes by using aryl diazonium silica sulfates under mild conditions

An efficient, fast and straightforward procedure for the synthesis of aryltriazenes is described in the present paper by using aryl diazonium silica sulfates and secondary amines. Using the present method, different kinds of aryl diazonium silica sulfates

Rhodium(III)-catalyzed C-H activation of arenes using a versatile and removable triazene directing Group

Diverse opportunities: A Rhodium(III)-catalyzed ortho-selective olefination of arenes using a novel triazene as a directing group is reported. This method exhibits substantial post-functionalization synthetic versatility, overcoming a vital limitation in Ca spa 2-H activation/functionalization products: restricted structural diversity. Copyright

Unusually stable, versatile, and pure arenediazonium tosylates: Their preparation, structures, and synthetic applicability

(Graph Presented) A new, simple, and effective method for the diazotization of a wide range of arylamines has been developed by using a polymer-supported diazotization agent in the presence of p-toluenesulfonic acid. Various pure arenediazonium tosylates with unusual stabilities can be easily prepared by this method. As a result, these salts are useful and versatile substrates for subsequent transformations, such as halogenation and Heck-type reactions. The unusual stabilities of arenediazonium tosylates are also preliminarily discussed with their X-ray structures.

Synthesis of Biaryls from Aryltriazenes

Aryltriazenes react with aromatic solvents in the presence of trifluoroacetic acid to produce biaryls.The mechanism of the reaction involves the formation of arenediazonium trifluoroacetates which lose nitrogen to give mainly aryl radicals.