6574-15-8

Basic information

• Product Name: 1-(4-Nitrophenyl)piperidine
• Synonyms: 1-Piperidino-4-nitrobenzene;BUTTPARK 96\57-87;AURORA 2061;1-(4-NITROPHENYL)PIPERIDINE;N-(4-NITROPHENYL)PIPERIDINE;4-CHLORO-2-AMINOPYRIMIDINE
• CAS NO: 6574-15-8
• Molecular Formula: C₁₁H₁₄N₂O₂
• Molecular Weight: 206.24
• EINECS: 229-492-7
• Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Piperidine;CHIRAL CHEMICALS
• Mol File: 6574-15-8.mol
• Article Data: 100

Chemical Properties

• Melting Point: 104-106°C
• Boiling Point: 363.5 °C at 760 mmHg
• Flash Point: 173.6 °C
• Appearance: /
• Density: 1.188 g/cm³
• Vapor Pressure: 9.68E-17mmHg at 25°C
• Refractive Index: 1.706
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.92±0.20(Predicted)
• CAS DataBase Reference: 1-(4-Nitrophenyl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Nitrophenyl)piperidine(6574-15-8)
• EPA Substance Registry System: 1-(4-Nitrophenyl)piperidine(6574-15-8)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: 20/21/22
• Safety Statements: 22-36
• Hazardous Substances Data: 6574-15-8(Hazardous Substances Data)

Usage

General Description

1-(4-Nitrophenyl)piperidine is a chemical compound with a molecular formula C11H14N2O2. It is a piperidine derivative that contains a nitrophenyl group attached to the piperidine ring. 1-(4-Nitrophenyl)piperidine is commonly used in the synthesis of various pharmaceuticals and research chemicals. It exhibits significant biological activity and is used in the development of potential drug candidates. 1-(4-Nitrophenyl)piperidine is also a versatile building block in organic synthesis, with applications in the production of agrochemicals, dyes, and other specialty chemicals. Due to its structural and pharmacological properties, 1-(4-Nitrophenyl)piperidine is an important intermediate in the development of new compounds for medical and industrial purposes.

InChI:InChI=1/C23H21N5O4S/c1-13-8-10-14(11-9-13)28-20(30)15-6-4-5-7-16(15)25-22(28)33-12-17(29)18-19(24)26(2)23(32)27(3)21(18)31/h4-11H,12,24H2,1-3H3

Upstream product

• 110-89-4 piperidine 
• 98-95-3 nitrobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 350-46-9 4-Fluoronitrobenzene 
• 4096-20-2 N-phenyl piperidine 
• 111-24-0 1,5-dibromo-pentane 
• 100-01-6 4-nitro-aniline 
• 100-17-4 para-methoxynitrobenzene 
• 17763-80-3 para-nitrophenyl triflate 
• 14150-94-8 3,5-dinitro-1-methyl-2-pyridone 
• 67-64-1 acetone 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 23493-34-7 1-methyl-3-nitropyridinium iodide 
• 626-67-5 N-methylcyclohexylamine 

Downstream Products

• 40832-54-0 1-(4-nitrophenyl)piperidine N-oxide 
• 78039-75-5 1-(4-nitrophenoxy)-piperidine 
• 79421-45-7 4-(4-hydroxypiperidinyl)nitrobenzene 
• 879896-41-0 4-(piperdin-1-yl)phenyl isocyanate 
• 6641-28-7 4-(piperidin-1-yl)aniline dihydrochloride 
• 1332527-53-3 4-{[3-(4-piperidin-1-ylphenylsulfamoyl)benzenesulfonylamino]methyl}piperidine-1-carboxylic acid tert-butyl ester 
• 1443155-73-4 N-(1,3-benzothiazol-2-ylmethyl)-4-(piperidin-1-yl)aniline 
• 30130-59-7 N-(4-(piperidin-1-yl)phenyl)formamide 
• 693235-85-7 N-(2''-methoxybenzyl)-4-(piperidin-1'-yl)aniline 

Relevant articles and documents

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Rate and Yield Enhancements in Nucleophilic Aromatic Substitution Reactions via Mechanochemistry

A variety of nucleophilic aromatic substitution reactions were carried out mechanochemically to great advantage. On average, reactions rates were nine-times faster. The corresponding kinetic studies presented provide the clearest head-to-head kinetic comparisons between mechanochemical and conventional systems at identical temperatures. Attempts are provided at classifying the kinetics of one example. Removal of polar, protic solvents from these reactions presents environmental benefits to a reaction class whose kinetics are heavily dependent on such solvents.

Nucleophilic aromatic substitution reactions under aqueous, mild conditions using polymeric additive HPMC

The use of the inexpensive, benign, and sustainable polymer, hydroxypropyl methylcellulose (HPMC), in water enables nucleophilic aromatic subsitution (SNAr) reactions between various nucleophiles and electrophiles. The mild reaction conditions facilitate a broad functional group tolerance that can be utilized for subsequent derivatization for the synthesis of pharmaceutically relevant building blocks. The use of only equimolar amounts of all reagents and water as reaction solvent reveals the greenness and sustainability of the methodology presented herein.

Discovery and SARs of 5-Chloro- N4-phenyl- N2-(pyridin-2-yl)pyrimidine-2,4-diamine Derivatives as Oral Available and Dual CDK 6 and 9 Inhibitors with Potent Antitumor Activity

Cyclin-dependent kinases (CDKs) are promising therapeutic targets for cancer therapy. Herein, we describe our efforts toward the discovery of a series of 5-chloro-N4-phenyl-N2-(pyridin-2-yl)pyrimidine-2,4-diamine derivatives as dual CDK6 and 9 inhibitors. Intensive structural modifications lead to the identification of compound 66 as the most active dual CDK6/9 inhibitor with balancing potency against these two targets and good selectivity over CDK2. Further biological studies revealed that compound 66 was directly bound to CDK6/9, resulting in suppression of their downstream signaling pathway and inhibition of cell proliferation by blocking cell cycle progression and inducing cellular apoptosis. More importantly, compound 66 significantly inhibited tumor growth in a xenograft mouse model with no obvious toxicity, indicating the promising therapeutic potential of CDK6/9 dual inhibitors for cancer treatment. Therefore, the above results are of great importance in the development of dual CDK6/9 inhibitors for cancer therapy.