92972-48-0

Basic information

• Product Name: 2,4-Dichloro-5-thiazolecarboxaldehyde
• Synonyms: BUTTPARK 121\04-87;IFLAB-BB F2124-0686;2,4-DICHLORO-5-THIAZOLECARBOXALDEHYDE;2,4-DICHLORO-5-FORMYLTHIAZOLE;2,4-DICHLOROTHIAZOLE-5-CARBALDEHYDE;2,4-DICHLOROTHIAZOLE-5-CARBOXALDEHYDE;2,4-DICHLOROTHIAZOL-5-CARBOXALDEHYDE;2,4-DICHLORO-1,3-THIAZOLE-5-CARBALDEHYDE
• CAS NO: 92972-48-0
• Molecular Formula: C₄HCl₂NOS
• Molecular Weight: 182.03
• Product Categories: API intermediates;Aldehyde;Organohalides;Thiazole;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Aldehydes;Building Blocks;C1 to C6;Carbonyl Compounds;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Organic Building Blocks;Thiazoles
• Mol File: 92972-48-0.mol

Chemical Properties

• Melting Point: 47-53℃
• Boiling Point: 307.1 °C at 760 mmHg
• Flash Point: >110°C
• Appearance: /
• Density: 1.69 g/cm³
• Vapor Pressure: 0.000741mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -3.71±0.10(Predicted)
• CAS DataBase Reference: 2,4-Dichloro-5-thiazolecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-5-thiazolecarboxaldehyde(92972-48-0)
• EPA Substance Registry System: 2,4-Dichloro-5-thiazolecarboxaldehyde(92972-48-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36/37/39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 92972-48-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dichloro-5-thiazolecarboxaldehyde is used as a key intermediate in the synthesis of thiazolidine-2,4-dione derivatives, which possess antimicrobial properties. These derivatives can be further utilized in the development of new antimicrobial agents to combat drug-resistant infections.
Used in Chemical Synthesis:
2,4-Dichloro-5-thiazolecarboxaldehyde is used as a versatile building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for a wide range of chemical reactions, making it a valuable component in the development of novel compounds with diverse applications.

InChI:InChI=1/C4HCl2NOS/c5-3-2(1-8)9-4(6)7-3/h1H

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 68-12-2 N,N-dimethyl-formamide 
• 4175-76-2 2,4-dichlorothiazole 
• 10025-87-3 trichlorophosphate 
• 17356-08-0 thiourea 
• 79-11-8 chloroacetic acid 

Downstream Products

• 170232-69-6 2,4-dichloro-5-(hydroxymethyl)thiazole 
• 1003-32-3 thiazole-5-carboxaldehyde 
• 139670-00-1 4-chloro-2-(piperidin-1-yl)thiazole-5-carbaldehyde 
• 129880-84-8 4-chloro-2-(morpholin-4-yl)-thiazole-5-carbaldehyde 
• 199851-22-4 4-chloro-2-tert-butylaminothiazole-5-carbaldehyde 
• 918131-29-0 2-benzylsulfanyl-4-chlorothiazole-5-carbaldehyde 
• 918131-30-3 2-p-methoxybenzylsulfanyl-4-chlorothiazole-5-carbaldehyde 

Relevant articles and documents

New thiazolyl-pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

A new series of N-substituted pyrazoline derivatives 6a–g, 7a–g, 8a–g, and 9a–g was synthetized by reaction of hydrazine derivatives and chalcone–thiazole hybrids bearing nitrogen mustard 5a–g. The chalcones 5a–g were obtained by Claisen–Schmidt condensation of thiazole-2-nitrogen mustard 3 and selected acetophenones 4a–g. These new compounds 6/7/8/9a–g were screened for their antifungal activity against Cryptococcus neoformans, with IC50 values of 3.9–7.8 μg/ml for the N-3,5-dichlorophenyl pyrazolines 9e–g. Interestingly, those compounds show low cytotoxic effects toward erythrocytes (RBC). In addition, N-acetyl (6a,b) and N-formyl pyrazolines (7a, 7b, 7c, and 7g) showed inhibitory activity against methicillin-susceptible Staphylococcus aureus, methicillin-resistant S. aureus, and vancomycin-intermediate S. aureus, with the most important minimum inhibitory concentration values ranging from 31.25 to 125 μg/ml. Regarding the antiprotozoal activity, thiazolyl-pyrazolines 9g, 8f, and 7c display high activity against Plasmodium falciparum, Leishmania (V) panamensis, and Trypanosoma cruzi, with EC50 values of 11.80, 6.46, and 4.98 μM, respectively, and with 7c being approximately 2.6-fold more potent than benznidazole with a selectivity index of 1.61 on U-937 human cells, showing promising potential as a novel antitrypanosomal agent.

Design and development of novel thiazole-sulfonamide derivatives as a protective agent against diabetic cataract in Wistar rats via inhibition of aldose reductase

In recent years, ALR2 (aldose reductase) inhibitors have attracted attention for their effective ability to reduce the progression of diabetes-associated cataracts. Therefore, in the present article, we intended to develop novel thiazole-sulfonamide hybrids as a potent inhibitor of ALR2. These molecules significantly inhibited the ALR2 level in the rat lenses homogenate, where the most potent compound 7b showed activity comparable to sorbinil as standard. In Wistar rats, compound 7b improved the insulin level and body weight of the experimental animal together with a reduction in the glucose output. Compound 7b showed a significant reduction in the expression of ALR2 in rat lenses in western blot analysis.

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.

Pyrimidine-thiazolidinone derivatives

Pyrimidine-thiazolidinone derivatives may be used for preventing or treating diseases in humans or animals, and have demonstrated efficacy specifically in treating type-2 diabetes. Methods of synthesizing the pyrimidine-thiazolidinone derivatives, described herein, can provide high yields in a short time and with high purity. The pyrimidine-thiazolidinone derivatives demonstrate improved hypoglycemic activity compared to most anti-diabetic drugs currently available.

Synthesis of carboxamide and sulfonyl carboxamide linked heterocycles under green conditions

Direct coupling of heteroaldehydes with heteroaryl amines / sulfonylamines is performed under green conditions using PEG-400 in the presence of oxidant CCl3CN/H2O2. The presence of electron withdrawing substituents on heteroaldehydes increased the yield. Further heteroaryl amines favor the reaction when compared with heteroaryl sulfonylamines.

Solvent-free synthesis of bis-hydrazones through 1,3-dipolar cycloaddition of sydnone and study of their optical, molecular docking, and antioxidant properties

A series of new 1-(aryl)-1H-pyrazol-3,4-bis (aryl)-3,4-dicarbohydrazones (4) was obtained by the condensation of 1-arylpyrazole-3,4-dicarbohydrazides (3) with various aryl aldehydes under solvent-free conditions. The structures of the newly synthesized hy

Synthesis, characterization and antioxidant property of novel series of thiazole based chalcones carrying thiophene/furan derivatives

Two novel series of thiazole based chalcones bearing thiophene or furan derivatives (4a-h and 5a-f) were synthesized by acid/base catalyzed Claisen Schimidt condensation reaction between thiazole carbaldehyde (2) with various substituted acetylfuran (3a) or acetylthiophene (3b). The structures of these newly synthesized compounds were confirmed by their 1H-NMR, IR, Mass spectral and elemental analytical data. All the new compounds were screened for their antioxidant activity.

THIAZOLE DERIVATIVES FOR THE TREATMENT OF ANIMAL TRYPANOSOMIASIS

The present invention relates to a novel class of compounds of general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, X and Y are as defined herein, to their use in human and veterinary medicine, and in the treatment of animal trypanosomiasis in particular, to compositions containing them, to processes for their preparation and to intermediates used in such processes.

HEPATITIS B CORE PROTEIN ALLOSTERIC MODULATORS

ABSTRACT The present disclosure provides, in part, compounds having allosteric effector properties against Hepatitis B virus Cp. Also provided herein are methods of treating viral infections, such as hepatitis B, comprising administering to a patient in need thereof a disclosed compound.

LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.