17969-22-1

Basic information

• Product Name: 4-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)-1,3-THIAZOLE
• Synonyms: 4-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)-1,3-THIAZOLE;4-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)THIAZOLE;Thiazole,4-(chloroMethyl)-2-(4-chlorophenyl)-;Thiazole, 4-(chloromethyl)-2-(p-chlorophenyl)-
• CAS NO: 17969-22-1
• Molecular Formula: C₁₀H₇Cl₂NS
• Molecular Weight: 244.14
• Mol File: 17969-22-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: 78 °C
• Boiling Point: 374 °C at 760 mmHg
• Flash Point: 180 °C
• Appearance: /
• Density: 1.378 g/cm³
• Vapor Pressure: 1.85E-05mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: 4-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)-1,3-THIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)-1,3-THIAZOLE(17969-22-1)
• EPA Substance Registry System: 4-(CHLOROMETHYL)-2-(4-CHLOROPHENYL)-1,3-THIAZOLE(17969-22-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 17969-22-1(Hazardous Substances Data)

Usage

General Description

4-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole is a chemical compound with the molecular formula C10H7Cl2NS. It belongs to the thiazole class of chemicals, which are heterocyclic compounds containing a five-membered ring with sulfur and nitrogen atoms. This specific compound is characterized by the presence of a chloromethyl group and a 4-chlorophenyl group. It is a potential building block for the synthesis of pharmaceutical and agrochemical products due to its unique structure and reactivity. It may also have applications in materials science and organic synthesis. However, it is important to handle this compound with caution as it may have harmful effects if not handled properly.

InChI:InChI=1/C10H7Cl2NS/c11-5-9-6-14-10(13-9)7-1-3-8(12)4-2-7/h1-4,6H,5H2

Upstream product

• 534-07-6 1,3-Dichloroacetone 
• 2521-24-6 4-chlorothiobenzamide 
• 623-03-0 4-Cyanochlorobenzene 
• 36093-99-9 [2-(4-chloro-phenyl)-thiazol-4-yl]-methanol 
• 61786-00-3 ethyl 2-(4-chlorophenyl)thiazole-4-carboxylate 
• 619-56-7 4-chlorobenzamide 

Downstream Products

• 36093-99-9 [2-(4-chloro-phenyl)-thiazol-4-yl]-methanol 
• 173192-01-3 4-[2-(4-Chloro-phenyl)-thiazol-4-ylmethoxy]-benzaldehyde 
• 1025878-18-5 {4-[2-(4-chloro-phenyl)-thiazol-4-ylmethoxy]-phenyl}-cyclohexyl-methanol 
• 1027933-90-9 O-({4-[2-(4-chloro-phenyl)-thiazol-4-ylmethoxy]-phenyl}-cyclohexyl-methyl)-hydroxylamine 
• 61329-09-7 2-[2-(4-chloro-phenyl)-thiazol-4-ylmethoxy]-2-methyl-propionic acid 
• 52041-83-5 [5-bromo-2-(4-chloro-phenyl)-thiazol-4-yl]-methanol 
• 52041-93-7 5-bromo-2-(4-chloro-phenyl)-thiazole-4-carbaldehyde 
• 52041-97-1 5-bromo-2-(4-chloro-phenyl)-thiazole-4-carboxylic acid 
• 620115-88-0 N-(3-{2-[2-(4-Chloro-phenyl)-thiazol-4-ylmethoxy]-ethyl}-phenyl)-C,C,C-trifluoro-methanesulfonamide 
• 544417-40-5 Capadenoson 
• 1143520-49-3 (1R)-N-((2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl)-1-(4-methylphenyl)ethanamine 
• 923526-95-8 2-(4-chlorophenyl)-4-((3-chlorophenylthio)methyl)thiazole 
• 501103-27-1 2-((2-(4-chlorophenyl)thiazol-4-yl)methylthio)aniline 
• 866357-72-4 4-((2-(4-chlorophenyl)thiazol-4-yl)methylthio)aniline 

Relevant articles and documents

Heterocycles 44. Synthesis, characterization and anticancer activity of new thiazole ortho-hydroxychalcones

A novel series of substituted thiazole ortho-hydroxychalcones was synthesized to be physico-chemically characterized and evaluated for the anticancer activity. The chalcones were synthesized with 28–68% yields, via Claisen–Schmidt condensation in an ethanolic solution. All the synthesized compounds were purified and characterized by MS, 1H NMR, 13C NMR, IR, and melting points. The cytotoxicity of thiazole ortho-hydroxychalcones 3a–3o as well as doxorubicin was determined in a panel of 9 cancer cell lines including sensitive and drug resistant phenotypes. Compounds 3a, 3b, 3c, 3j, as well as doxorubicin displayed cytotoxic effects in all the 9 tested cancer cell lines with IC50 values below 75 μM. The best samples showed IC50 values below 10 μM against 5/9 cancer cell lines for 3a, 3h, and 3o, against 7/9 cancer cell lines for 3c and 3f, and against 8/9 cancer cell lines for 3j. Hypersensitivity of all resistant cells towards 3b, 3g, 3j, 3m, and 3o was also obtained, suggesting that these compounds are appropriate molecules that could be used to combat drug resistance of cancer cells.

Design, synthesis, fungicidal activities and structure–activity relationship studies of (?)-borneol derivatives containing 2-aryl-thiazole scaffold

A series of (-)-borneol derivatives containing 2-aryl-thiazole scaffold were designed, synthesized, and characterized by 1H NMR, 13C NMR, and HRMS. The fungicidal activities of these novel compounds against Fusarium oxysporum, Magnaporthe grisea, Botrytis cinerea, and Penicillium digitatum were evaluated. The results indicated that (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl(Z)-4-oxo-4-(((2-phenylthiazol-4-yl)methyl)amino)but-2-enoate (6a) displayed potential fungicidal activities with broad spectrum. Especially, 6a exhibited an IC50 value of 48.5 mg/L against P. digitatum, which has higher fungicidal activity than commercial products hymexazol and amicarthiazol. Moreover, (1S,2R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl-4-oxo-4-(((2-phenylthiazol-4-yl)methyl)amino)butanoate (5a) possesses an IC50 value of 24.3 mg/L against B. cinerea, comparable to hymexazol and far superior to amicarthiazol. Furthermore, the superficial structure–activity relationship was discussed, which might be helpful for discovering novel fungicides.

Neladenoson Bialanate Hydrochloride: A Prodrug of a Partial Adenosine A1 Receptor Agonist for the Chronic Treatment of Heart Diseases

Adenosine is known to be released under a variety of physiological and pathophysiological conditions to facilitate the protection and regeneration of injured ischemic tissues. The activation of myocardial adenosine A1 receptors (A1Rs) has been shown to inhibit myocardial pathologies associated with ischemia and reperfusion injury, suggesting several options for new cardiovascular therapies. When full A1R agonists are used, the desired protective and regenerative cardiovascular effects are usually overshadowed by unintended pharmacological effects such as induction of bradycardia, atrioventricular (AV) blocks, and sedation. These unwanted effects can be overcome by using partial A1R agonists. Starting from previously reported capadenoson we evaluated options to tailor A1R agonists to a specific partiality range, thereby optimizing the therapeutic window. This led to the identification of the potent and selective agonist neladenoson, which shows the desired partial response on the A1R, resulting in cardioprotection without sedative effects or cardiac AV blocks. To circumvent solubility and formulation issues for neladenoson, a prodrug approach was pursued. The dipeptide ester neladenoson bialanate hydrochloride showed significantly improved solubility and exposure after oral administration. Neladenoson bialanate hydrochloride is currently being evaluated in clinical trials for the treatment of heart failure.