114393-97-4

Basic information

• Product Name: 4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzyaldehyde
• Synonyms: 4-[2-(5-Ethyl-2-Pyridyl)Ethoxy]-Benzaldehyde;4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-benzaldehyde;4-[2-(5-ETHYL-2-PYRIDINYL)ETHOXY]BENZYALDEHYDE;4-[2-(5-ETHYL-2-PYRIDINYL)ETHOXY]BENZALDEHYDE;4-[2-(5-Ethyl-3-pyridyl)ethoxy]benzaldehyde;Pioglitazone Aldehyde IMpurity
• CAS NO: 114393-97-4
• Molecular Formula: C₁₆H₁₇NO₂
• Molecular Weight: 255.31
• Product Categories: Aromatics;Heterocycles;Intermediates
• Mol File: 114393-97-4.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 431.82 °C at 760 mmHg
• Flash Point: 214.957 °C
• Appearance: Off-white low melting solid
• Density: 1.118 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: -20?C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 5.45±0.22(Predicted)
• CAS DataBase Reference: 4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzyaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzyaldehyde(114393-97-4)
• EPA Substance Registry System: 4-[2-(5-Ethyl-2-pyridinyl)ethoxy]benzyaldehyde(114393-97-4)

Safety Data

• Hazardous Substances Data: 114393-97-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Low Melting Solid

Uses

An intermediate of Pioglitazone (P471000).

InChI:InChI=1/C16H17NO2/c1-2-13-3-6-15(17-11-13)9-10-19-16-7-4-14(12-18)5-8-16/h3-8,11-12H,2,9-10H2,1H3

Upstream product

• 58765-11-0 4-hydroxybenzaldehyde potassium salt 
• 123-08-0 4-hydroxy-benzaldehyde 
• 144809-27-8 toluene-4-sulfonic acid 2-(5-ethylpyridin-2-yl)ethyl ester 
• 5223-06-3 5-ethyl-2-(2-hydroxyethyl)pyridine 
• 1122-91-4 4-bromo-benzaldehyde 
• 87199-17-5 4-formylphenylboronic acid, 
• 23616-79-7 benzyltri(n-butyl)ammonium chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 1194-02-1 4-fluorobenzonitrile 
• 144809-26-7 2-(5-ethyl-pyridin-2-yl)ethyl methanesulfonate 
• 136402-00-1 4-[2-(5-ethylpyridin-2-yl)ethoxy] benzonitrile 

Downstream Products

• 1026070-99-4 2-Methyl-benzoic acid [1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-hydrazide 
• 136401-69-9 5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzylidene}-2,4-thiazolidinedione 
• 144809-28-9 5-{4-[2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione 
• 136401-70-2 (E)-5-<4-<2-(5-Ethyl-2-pyridyl)ethoxy>benzylidene>-2,4-thiazolidinedione 
• 105355-27-9 Pioglitazone 
• 312690-32-7 2-[1-{4-[2-(5-Ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid ethyl ester 

Relevant articles and documents

Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist

Abstract: The present work describes the design, synthesis, molecular docking, biological evaluation, and assessment of structure–activity relationship of new derivatives based upon the molecular skeleton of the drug pioglitazone, a compound which is currently used for the management of type 2 diabetes mellitus. Pioglitazone has several side effects such as weight gain, edema, congestive heart failure, and bladder cancer. Therefore, there is a strong demand for identification of new lead candidates in the treatment of type 2 diabetes mellitus. A series of 24 compounds were prepared and evaluated for their peroxisome proliferator-activated receptor-γ (PPARγ) binding affinity assay and the IC50 values were determined. Among these compounds, six compounds exhibited promising IC50 values as compared to standard drugs pioglitazone and rosiglitazone. Furthermore, in order to confirm the target of these molecules, molecular docking study was carried out with peroxisome proliferator-activated receptor-γ (PPARγ) protein. Molecular modeling studies suggested that these compounds appropriately interact in the active sites of receptor. Graphical abstract: [Figure not available: see fulltext.].

Phosphoryl chloride mediated synthesis of 5-arylidene-2,4- thiazolidinediones derivatives via aromatic bisulfite adducts

The carbon-carbon bond formation by the condensation of bisulfite adduct of aromatic aldehydes with thiazolidine-2, 4-dione to furnish 5-arylidene-2,4- thiazolidinedione's has been investigated. This novel methodology was applied to convert substituted aryl bisulfite adducts to corresponding 5-arylidene-2,4-thiazolidinedione's with POCl3 in less-polar solvents such as toluene, chlorobenzene and o-xylene. 5-(4-methoxybenzylidene) thiazolidine-2,4-dione and 5-(4-ethoxybenzylidene)thiazolidine-2,4-dione were obtained in good yields.