26815-04-3

Basic information

• Product Name: 4-[2-(1-Piperidinyl)ethoxy]benzaldehyde
• Synonyms: ASISCHEM C56804;4-(2-piperidine-1-ethyloxy)benzaldehyde;4-(2-PIPERIDINYLETHOXY) BENZALDEHYDE;4-[2-(1-PIPERIDINYL) ETHOXY] BENZALDEHYDE;AKOS BC-2071;PIPEB;4-[2-(N-Piperidyl)]Ethoxybenzaldehyde98%;4-(2-Piperidin-1-Yl-Ethoxy)Benzaldehyde
• CAS NO: 26815-04-3
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• Mol File: 26815-04-3.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 378.5°C at 760 mmHg
• Flash Point: 182.7°C
• Appearance: /
• Density: 1.084g/cm³
• Vapor Pressure: 6.25E-06mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-[2-(1-Piperidinyl)ethoxy]benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[2-(1-Piperidinyl)ethoxy]benzaldehyde(26815-04-3)
• EPA Substance Registry System: 4-[2-(1-Piperidinyl)ethoxy]benzaldehyde(26815-04-3)

Safety Data

• Hazardous Substances Data: 26815-04-3(Hazardous Substances Data)

Usage

General Description

4-[2-(1-Piperidinyl)ethoxy]benzaldehyde is a chemical compound with the molecular formula C14H19NO2. Its exact mass is 231.1422 g/mol and its monoisotopic mass is 231.141907 g/mol. The polarity of this compound is characterized by a fairly even distribution of electrons, hence an almost uniform negative and positive charge throughout the molecule. 4-[2-(1-Piperidinyl)ethoxy]benzaldehyde is commonly used in the field of organic synthesis, having convenient properties for the production of a variety of organic compounds. Details about its toxicity or usage restrictions are not readily available, suggesting it's mostly employed in controlled industrial or laboratory environments.

InChI:InChI=1/C14H19NO2/c16-12-13-4-6-14(7-5-13)17-11-10-15-8-2-1-3-9-15/h4-7,12H,1-3,8-11H2

Upstream product

• 1932-03-2 2-(piperidin-4-yl)ethyl chloride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 2008-75-5 N-chloroethylpiperidine hydrochloride 
• 223251-13-6 [4-[2-(1-piperidinyl)ethoxy]phenyl]methanol 
• 584-08-7 potassium carbonate 
• 408538-22-7 N-hydroxyethylpiperidine 
• 3040-44-6 1-piperidinoethanol 
• 110-89-4 piperidine 
• 52191-15-8 4-(2-bromoethyloxy)benzaldehyde 
• 54373-15-8 4-(2-chloroethoxy)benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 104396-95-4 [2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-butyl]-[4-(2-piperidino-ethoxy)-benzyl]-amine 
• 136135-80-3 1,3,3-Trimethyl-5-[1-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-meth-(Z)-ylidene]-2-oxa-bicyclo[2.2.2]octan-6-one 
• 223251-13-6 [4-[2-(1-piperidinyl)ethoxy]phenyl]methanol 
• 151533-32-3 2-(4''-[2'''-piperidinoethoxy]phenyl)-3-(4'-tetrahydropyranyloxyphenyl)-7-tetrahydropyranyloxy-2,3-dihydro-4H-1-benzopyran-4-one 
• 130064-36-7 2-[4-[2-(1-piperidino)-ethoxy]phenyl]-3-[4-hydroxyphenyl]-7-hydroxy-2H-1-benzopyran 
• 690274-17-0 3-methyl-2-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-7-(tetrahydro-pyran-2-yloxy)-chroman-4-one 
• 690274-21-6 7-(tert-butyl-dimethyl-silanyloxy)-3-isopropyl-2-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-chroman-4-one 
• 265654-08-8 7-hydroxy-3-(4-hydroxy-phenyl)-2-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-chroman-4-one 

Relevant articles and documents

Evaluation of 2-(piperidine-1-yl)-ethyl (PIP) as a protecting group for phenols: Stability to ortho-lithiation conditions and boiling concentrated hydrobromic acid, orthogonality with most common protecting group classes, and deprotection via Cope elimination or by mild Lewis acids

A new protecting group, 2-(piperidine-1-yl)-ethyl (PIP), was evaluated as a protecting group for phenols. The PIP group was stable to ortho-lithiation conditions and refluxing with concentrated hydrobromic acid. Deprotection was accomplished by two routes, oxidation to N-oxides followed by Cope elimination (CE) and subsequent hydrolysis or ozonolysis of the vinyl ether or one-step deprotection by BBr3?Me2S. The PIP group is orthogonal to the O-benzyl, O-acetyl, O-t-butyldiphenylsilyl, O-methyl, O-p-methoxybenzyl, O-allyl, O-tetrahydropyranyl and N-t-butoxy carbonyl groups. The CE step was systematically studied and was found to give higher yields when the reaction was performed in the presence of silylating agents.

Design, synthesis and biological evaluation of novel 4-anlinoquinazoline derivatives as EGFR inhibitors with the potential to inhibit the gefitinib-resistant nonsmall cell lung cancers

A series of quinazoline derivatives with benzylidene hydrazine carboxamide were designed and synthesised as EGFR inhibitors. Most compounds exhibited exceptional anti-proliferative activity against A549, HepG2, MCF-7 and H1975 cells. Furthermore, six compounds demonstrated excellent inhibition activity against EGFRWT with the IC50 value both less than 2 nM. Among the six compounds, 44 exhibited the strongest activity (0.4 nM) and potently inhibited EGFRL858R/T790M (0.1 μM). Excitingly, the most potent compound 14 showed excellent enzyme inhibitory activity with 6.3 nM and 8.4 nM for both EGFRWT and EGFRT790M/L858R. The result of AO single staining and Annexin V/PI staining showed that the compound 14 and 44 could induce remarkable apoptosis of A549 cells. The compound 14 arrested the cell cycle at the S phase and compound 44 arrested the cell cycle at the G0 phase in A549 cells. These preliminary results demonstrate that compound 14 and 44 may be promising lead compound-targeting EGFR.

TOLL-LIKE RECEPTOR SIGNALING INHIBITORS

Di- and triaryl-substituted heteroaromatic compounds have Toll-like receptor inhibitory activity, including at TLR2, TLR4, TLR7, and/or TLR9. Compounds and compositions have applications in the treatment of diseases and conditions mediated by Toll-like receptors and related receptors, such as bacterial sepsis, autoimmune disease, lupus erythematosus, ischemia-reperfusion injury, stroke, metabolic disease, obesity-related metabolic inflammation, gout, and cancer.