2359-60-6

Basic information

• Product Name: 4-Piperidinoaniline
• Synonyms: 4-PIPERIDIN-1-YLANILINE;4-PIPERIDINOANILINE;N-(4-AMINOPHENYL)PIPERIDINE;TIMTEC-BB SBB010087;4-Piperidinoaniline,98%;1-(p-Aminophenyl)piperidine;4-(1-PIPERIDINO)ANILINE [1-(4-AMINOPHENYL)PIPERIDINE];4-(1-PIPERIDINO)ANILINE, 97+%
• CAS NO: 2359-60-6
• Molecular Formula: C₁₁H₁₆N₂
• Molecular Weight: 176.26
• Product Categories: Amines and Anilines;Heterocycles;Amines;Phenyls & Phenyl-Het;Building Blocks;Heterocyclic Building Blocks;Piperidines
• Mol File: 2359-60-6.mol
• Article Data: 41

Chemical Properties

• Melting Point: 26-29 °C(lit.)
• Boiling Point: 140-142°C 1mm
• Flash Point: >230 °F
• Appearance: /
• Density: 1.074 g/cm³
• Vapor Pressure: 6.32E-05mmHg at 25°C
• Refractive Index: n20/D 1.5937(lit.)
• Storage Temp.: 2-8°C
• PKA: 7.79±0.10(Predicted)
• BRN: 139525
• CAS DataBase Reference: 4-Piperidinoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Piperidinoaniline(2359-60-6)
• EPA Substance Registry System: 4-Piperidinoaniline(2359-60-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36/37-20/21/22
• Safety Statements: 26-36-36/37/39-22
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2359-60-6(Hazardous Substances Data)

Usage

Description

4-Piperidinoaniline, also known as 4-(4-Aminophenyl)piperidine, is an organic compound with a molecular formula of C11H16N2. It is a white crystalline solid and is used as a chemical intermediate in the synthesis of various pharmaceuticals and other organic compounds.

Uses

Used in Pharmaceutical Industry:
4-Piperidinoaniline is used as a reactant for the synthesis of various pharmaceutical compounds, including:
1. Amino acid arylamides: These are used as selective interleukin-2 inducible T-cell inhibitors, which can be beneficial in the treatment of autoimmune diseases and transplantation.
2. Antimalarial drugs: 4-Piperidinoaniline serves as a key intermediate in the synthesis of antimalarial medications, contributing to the development of new treatments for this life-threatening disease.
3. Aglycoristocetin derivatives: These derivatives exhibit anti-influenza virus activity, making 4-Piperidinoaniline an essential component in the development of new antiviral drugs.
4. IRAK-4 inhibitors: As a reactant, 4-Piperidinoaniline is used in the synthesis of IRAK-4 inhibitors, which are potential therapeutic agents for the treatment of inflammatory diseases.
5. 9-Aminoacridines: These compounds, derived from 4-Piperidinoaniline, possess antiprion activity, which is crucial in the research and development of treatments for prion-related diseases.

InChI:InChI=1/C11H16N2/c12-10-4-6-11(7-5-10)13-8-2-1-3-9-13/h4-7H,1-3,8-9,12H2

Upstream product

• 4096-20-2 N-phenyl piperidine 
• 100-00-5 4-chlorobenzonitrile 
• 110-89-4 piperidine 
• 106-39-8 bromochlorobenzene 
• 106-47-8 4-chloro-aniline 
• 106-40-1 4-bromo-aniline 
• 586-78-7 para-nitrophenyl bromide 
• 1207-69-8 9-Chloroacridine 
• 6574-15-8 1-(4-nitrophenyl)piperidine 
• 127-63-9 diphenyl sulphone 
• 350-46-9 4-Fluoronitrobenzene 
• 111-24-0 1,5-dibromo-pentane 
• 106-50-3 1,4-phenylenediamine 
• 61083-49-6 N-(p-nitrophenyl)pyridinium chloride 

Downstream Products

• 251371-32-1 1-cyclopentyl-7-[4-(piperidin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one 
• 25556-16-5 1,4-di-(1-piperidinyl)benzene 

Relevant articles and documents

Triphenylamine-based redox-active aramids with 1-piperidinyl substituent as an auxiliary donor: Enhanced electrochemical stability and electrochromic performance

A new triphenylamine-based diamine monomer 4,4′-diamino-4″-(1-piperidinyl)triphenylamine was synthesized and polymerized with various aromatic dicarboxylic acids via the phosphorylation polyamidation technique leading to a series of redox-active aromatic polyamides (aramids). All the aramids exhibit good solubility in many organic solvents and can be solution-cast into flexible and strong films with high thermal stability. Cyclic voltammograms of the polymer films on the indium-tin oxide (ITO)-coated glass substrate exhibit a pair of well-defined and reversible oxidation waves with very low onset potentials of 0.27–0.35?V (vs. Ag/AgCl) in acetonitrile solution, with a strong color change from colorless neutral form to green and deep blue oxidized forms in the range of 0.75–1.20?V. The optical transmittance change (Δ%T) at 636?nm between the neutral state and the fully oxidized state is up to 83%.

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

Method for preparing amine through catalytic reduction of nitro compound by cyclic (alkyl) (amino) carbene chromium complex

The cyclic (alkyl) (amino) carbene chromium complex is prepared from corresponding ligand salt, alkali and CrCl3 and used for catalyzing pinacol borane to reduce nitro compounds in an ether solvent under mild conditions to generate corresponding amine. The method for preparing amine has the advantages of cheap and accessible raw materials, mild reaction conditions, wide substrate application range, high selectivity and the like, and is simple to operate.

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.