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

• 1207-69-8 9-Chloroacridine 
• 6574-15-8 1-(4-nitrophenyl)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 
• 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 
• 4096-20-2 N-phenyl piperidine 

Downstream Products

• 252900-55-3 (4-(3-methyl-2,5-dioxo-3-pyrrolinyl)phenyl)piperidine 
• 1383478-89-4 C₃₀H₃₅N₃OS 
• 51317-65-8 1-(4-isothiocyanatophenyl)piperidine 
• 1332527-53-3 4-{[3-(4-piperidin-1-ylphenylsulfamoyl)benzenesulfonylamino]methyl}piperidine-1-carboxylic acid tert-butyl ester 
• 1418221-36-9 C₂₅H₃₃N₃O₃S 
• 1403815-97-3 5-phenyl-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine 
• 1403885-38-0 (8-methoxy-2H-pyrazolo[3,4-c]quinolin-4-yl)-(4-piperidin-1-yl-phenyl)-amine 
• 1403885-74-4 (8-bromo-2H-pyrazolo[3,4-c]quinolin-4-yl)-(4-piperidin-1-yl-phenyl)-amine 
• 1394169-67-5 (S)-benzyl 3-(4-(piperidin-1-yl)phenylcarbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 892491-44-0 C₁₃H₁₈N₄O₂ 

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%.

Optimization of WZ4003 as NUAK inhibitors against human colorectal cancer

NUAK, the member of AMPK (AMP-activated protein kinase) family of protein kinases, is phosphorylated and activated by the LKB1 (liver kinase B1) tumor suppressor protein kinase. Recent work has indicated that NUAK1 is a key component of the antioxidant stress response pathway, and the inhibition of NUAK1 will suppress the growth and survival of colorectal tumors. As a promising target for anticancer drugs, few inhibitors of NUAK were developed. With this goal in mind, based on NUAK inhibitor WZ4003, a series of derivatives has been synthesized and evaluated for anticancer activity. Compound 9q, a derivative of WZ4003 by removing a methoxy group, was found to be the most potential one with stronger inhibitory against NUAK1/2 enzyme activity, tumor cell proliferation and inducing apoptosis of tumor cells. By in vivo efficacy evaluations of colorectal SW480 xenografts, 9q suppresses tumor growth more effectively with an excellent safety profile in vivo and is therefore seen as a suitable candidate for further investigation.

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.

Synthesis and Structure-Activity Relationships of Arylsulfonamides as AIMP2-DX2 Inhibitors for the Development of a Novel Anticancer Therapy

AIMP2-DX2, a splicing variant of AIMP2, is up-regulated in lung cancer, possesses oncogenic activity, and results in tumorigenesis. Specifically inhibiting the interaction between AIMP2-DX2 and HSP70 to suppress AIMP2-DX2-dependent cancers with small molecules is considered a promising avenue for cancer therapeutics. Optimization of hit BC-DXI-04 (IC50 = 40.1 μM) provided new potent sulfonamide based AIMP2-DX2 inhibitors. Among these, BC-DXI-843 showed improved inhibition against AIMP2-DX2 (IC50 = 0.92 μM) with more than 100-fold selectivity over AIMP2 in a luciferase assay. Several binding assays indicated that this compound effectively induces cancer cell apoptosis by specifically interrupting the interaction between DX2 and HSP70, which leads to the degradation of DX2 via Siah1-mediated ubiquitination. More importantly, BC-DXI-843 demonstrated in vivo efficacy in a tumor xenograft mouse model (H460 cells) at a dosage of 50 mg/kg, suggesting it as a promising lead for development of novel therapeutics targeting AIMP2-DX2 in lung cancer.