139670-00-1

Basic information

• Product Name: 4-CHLORO-2-(1-PIPERIDINO)-5-THIAZOLECARBOXALDEHYDE
• Synonyms: AKOS BBS-00006706;4-CHLORO-2-PIPERIDIN-1-YL-THIAZOLE-5-CARBALDEHYDE;4-CHLORO-2-PIPERIDIN-1-YL-1,3-THIAZOLE-5-CARBALDEHYDE;4-CHLORO-2-(1-PIPERIDINO)-5-THIAZOLECARBOXALDEHYDE;4-CHLORO-2-(1-PIPERIDINO)-5-THIAZOLECARBOXALDEHYDE, 95+%
• CAS NO: 139670-00-1
• Molecular Formula: C₉H₁₁ClN₂OS
• Molecular Weight: 230.71
• EINECS: 604-604-1
• Mol File: 139670-00-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 368°Cat760mmHg
• Flash Point: 176.3°C
• Appearance: /
• Density: 1.373g/cm³
• Vapor Pressure: 1.32E-05mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-CHLORO-2-(1-PIPERIDINO)-5-THIAZOLECARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2-(1-PIPERIDINO)-5-THIAZOLECARBOXALDEHYDE(139670-00-1)
• EPA Substance Registry System: 4-CHLORO-2-(1-PIPERIDINO)-5-THIAZOLECARBOXALDEHYDE(139670-00-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 139670-00-1(Hazardous Substances Data)

Usage

Description

4-Chloro-2-(1-piperidino)-5-thiazolecarboxaldehyde is an organic compound with the molecular formula C9H9ClN2OS. It is characterized by its thiazolecarboxaldehyde structure, which features a thiazole ring fused with a carbaldehyde group. The presence of a chloro and piperidino group further enhances its chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-(1-piperidino)-5-thiazolecarboxaldehyde is used as a reagent for the synthesis of thiazolyl thiazolidinedione derivatives. These derivatives serve as aldose reductase inhibitors, which are crucial in preventing sorbitol accumulation in tissues. This application is particularly relevant in the treatment of diabetic complications, such as neuropathy and retinopathy, where uncontrolled sorbitol accumulation can lead to cellular damage and impaired function.

InChI:InChI=1/C9H11ClN2OS/c10-8-7(6-13)14-9(11-8)12-4-2-1-3-5-12/h6H,1-5H2

Upstream product

• 2591-86-8 N-Formylpiperidine 
• 4175-76-2 2,4-dichlorothiazole 
• 68-12-2 N,N-dimethyl-formamide 
• 110-89-4 piperidine 
• 92972-48-0 2,4-dichlorothiazole-5-carboxaldehyde 

Downstream Products

• 919016-57-2 4-methoxy-2-piperidino-1,3-thiazole-5-carbaldehyde 
• 919016-59-4 C₁₁H₁₆N₂O₂S 
• 1242339-51-0 C₁₈H₂₀N₂O₂S 
• 1242339-39-4 C₁₇H₁₇ClN₂OS 

Relevant articles and documents

Ultrasound promoted montmorillonite K-10 catalyzed synthesis, characterization, molecular modelling, SAR and hypoglycemic studies of new rhodanine bejeweled acridine analogues

In the present work an efficient ultrasound promoted synthesis of (Z)-2-((4-chloro-2-(piperidin/morpholin-1-yl)thiazol-5-yl)methylene)-3,3,7,9 tetra methyl-3,4-dihydroacridin-1 (2H) -one analogues 6(a-h) via Knoevenagel condensation using MK-10 catalyst have been reported. MK-10 due to its diverse properties and high surface area to volume ratio exhibits favorable features for the reaction response such as the shorter reaction time, simple work-up procedure, clean reaction profiles and excellent product yields through reusability of the catalyst upto five cycles. In silico molecular docking studies were carried out to find out the effective binding affinity of the synthesized acridine analogues towards PPARγ protein (Id-2XKW). The results obtained showed that compounds 6c and 6g possess good binding interaction towards PPARγ with binding energy of -9.6 and -9.0 k.cal/mol which was greater than standard Acarbose (-8.9 k.cal/mol) and comparable to that of standard pioglitazone (-9.8 k.cal/mol). In vitro α-amylase and α-glucosidase assays were performed for hypoglycemic activity evaluation. The compounds 6c and 6g at a concentration of 100 μg/mL showed 87.18 ± 0.90 and 83.34 ± 0.15 percent inhibition towards α-glucosidase, 85.24 ± 1.06 and 80.76 ± 0.55 percent inhibition towards α-amylase which was higher than standard pioglitazone and on par to that of Acarbose.

Thiazole analogs of chalcones, capable of functionalization at the heterocyclic nucleus

The synthesis of new amino and alkoxy derivatives of thiazole-5- carbaldehyde, on the basis of which a,β-unsaturated ketones of the thiazole series were synthesized, are described in this paper. The possibility of obtaining chalcones and variation of substitution reactions in the thiazole ring has been shown. 2010 Springer Science+Business Media, Inc.

Preparation and characterisation of N-disubstituted 2-amino-4-chloro-5-formyl-thiazoles and their dicyanmethylene derivatives

In contrast to N-disubstituted 3-hydroxy-anilines 5 which react with the Vilsmeier reagent to N-substituted 4-amino-salicylaldehydes 7 their heteroanalogous N-disubstituted 2-amino-4-hydroxy-thiazoles 6 react with the same reagent to N-substituted 2-amino