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 
• 636-98-6 p-nitrobenzene iodide 
• 17763-80-3 para-nitrophenyl triflate 
• 14150-94-8 3,5-dinitro-1-methyl-2-pyridone 
• 67-64-1 acetone 
• 626-67-5 N-methylcyclohexylamine 
• 111-30-8 Glutaraldehyde 
• 121409-84-5 4-(4-Nitro-phenylcarbamoyl)-butyric acid methyl ester 

Downstream Products

• 192323-89-0 4-piperidino-cyclohexylamine 
• 2359-60-6 4-(1-piperidino)aniline 
• 839-93-0 1-(2,4-dinitrophenyl)piperidine 
• 40832-54-0 1-(4-nitrophenyl)piperidine N-oxide 
• 78039-75-5 1-(4-nitrophenoxy)-piperidine 
• 79421-45-7 4-(4-hydroxypiperidinyl)nitrobenzene 
• 6641-28-7 4-(piperidin-1-yl)aniline dihydrochloride 
• 1393367-48-0 1-(4-azidophenyl)piperidine 
• 1393367-61-7 1-(4-(4-((4-chlorophenox)ymethyl)-1H-1,2,3-triazol-1-yl)phenyl)piperidine 
• 1393367-62-8 1-(4-(4-(p-tolyloxymethyl)-1H-1,2,3-triazol-1-yl)-phenyl)piperidine 
• 1443155-73-4 N-(1,3-benzothiazol-2-ylmethyl)-4-(piperidin-1-yl)aniline 
• 379255-22-8 2-chloro-N-(4-(piperidin-1-yl)phenyl)acetamide 
• 30130-59-7 N-(4-(piperidin-1-yl)phenyl)formamide 

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 of benzo[d]oxazole derivatives as the potent type-I FLT3-ITD inhibitors

Fms-like tyrosine kinase 3 (FLT3) has been considered as a potential drug target for the treatment of acute myeloid leukemia (AML), because of its high and aberrant expression in AML patients, especially the patients with FLT3-ITD mutation. Initiating from a hit compound (IC50: 500 nM against FLT3-ITD), a series of compounds were designed and synthesized based on benzo[d]oxazole-2-amine scaffold to discover new potent FLT3-ITD inhibitors. During the medicinal chemistry works, flexible molecular docking was used to provide design rationale and study the binding modes of the target compounds. Through the mixed SAR exploration based on the enzymatic and cellular activities, compound T24 was identified with potent FLT3-ITD inhibitory (IC50: 0.41 nM) and anti-proliferative (IC50: 0.037 μM against MV4-11 cells) activities. And the binding mode of T24 with “DFG-in” FLT3 was simulated by a 20-ns molecular dynamics run, providing some insights into further medicinal chemistry efforts toward novel FLT3 inhibitors in AML therapy.