4771-31-7

Basic information

• Product Name: 4-(Chloromethyl)-2-phenyl-1,3-thiazole
• Synonyms: 4-(CHLOROMETHYL)-2-PHENYL-1,3-THIAZOLE;4-chloromethyl-2-phenylthiazole;4-(chloromethyl)-2-phenyl-1,3-thiazole(SALTDATA: FREE);2-Phenyl-4-(chloroMethyl)thiazole;Thiazole, 4-(chloroMethyl)-2-phenyl-;4-(Chloromethyl)-2-phenyl-1,3-thiazole 97%;4-(Chloromethyl)-2-phenyl-1,3-thiazole97%
• CAS NO: 4771-31-7
• Molecular Formula: C₁₀H₈ClNS
• Molecular Weight: 209.7
• Product Categories: Heterocycle
• Mol File: 4771-31-7.mol
• Article Data: 49

Chemical Properties

• Melting Point: 49 °C
• Boiling Point: 349.2 °C at 760 mmHg
• Flash Point: 165 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 9.64E-05mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: 2-8°C
• PKA: 0.22±0.10(Predicted)
• CAS DataBase Reference: 4-(Chloromethyl)-2-phenyl-1,3-thiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Chloromethyl)-2-phenyl-1,3-thiazole(4771-31-7)
• EPA Substance Registry System: 4-(Chloromethyl)-2-phenyl-1,3-thiazole(4771-31-7)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3261
• HazardClass: IRRITANT
• Hazardous Substances Data: 4771-31-7(Hazardous Substances Data)

Usage

General Description

4-(Chloromethyl)-2-phenyl-1,3-thiazole is a chemical compound that consists of a thiazole ring with a chloromethyl group and a phenyl group attached. It is commonly used in organic synthesis and pharmaceutical research, as it possesses potential bioactive properties and can be modified to create new compounds with desirable pharmacological effects. The chloromethyl group provides a site for further functionalization, allowing for the introduction of different chemical groups and enhancing the compound's versatility in creating new molecules. Additionally, the presence of the thiazole ring can impart specific biological activities, making it an important building block for drug discovery and development. Its unique structure and reactivity make 4-(Chloromethyl)-2-phenyl-1,3-thiazole a valuable tool in the field of medicinal chemistry.

InChI:InChI=1/C10H8ClNS/c11-6-9-7-13-10(12-9)8-4-2-1-3-5-8/h1-5,7H,6H2

Upstream product

• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 59937-01-8 2-phenylthiazole-4-carboxylic acid ethyl ester 
• 55-21-0 benzamide 
• 23780-13-4 (2-phenylthiazol-4-yl)methanol 
• 100-47-0 benzonitrile 
• 75-34-3 1,1-dichloroethane 
• 534-07-6 1,3-Dichloroacetone 
• 2227-79-4 benzenecarbothioamide 
• 37128-19-1 4-chloromethyl-2-phenyl-4,5-dihydro-thiazol-4-ol 

Downstream Products

• 1244030-71-4 2-amino-3-cyano-7-(dimethylamino)-4-(2-phenylthiazol-4-yl)-4H-chromene 
• 79116-16-8 methyl 2-(2-phenyl-4-thiazolylmethoxy)benzoate 
• 79116-17-9 methyl 2-(2-phenyl-4-thiazolylmethylthio)benzoate 
• 103787-86-6 5-[4-(2-Phenyl-thiazol-4-ylmethoxy)-benzyl]-thiazolidine-2,4-dione 
• 103789-67-9 4-((2-phenylthiazol-4-yl)methoxy)benzaldehyde 
• 4771-34-0 4-chloromethyl-5-nitro-2-phenyl-thiazole 
• 4771-33-9 5-chloro-4-chloromethyl-2-phenyl-thiazole 
• 17386-38-8 1,1-bis-(2-phenyl-thiazol-4-ylmethyl)-pyrrolidinium; chloride 
• 63484-66-2 2-bromo-10-(2-phenyl-thiazol-4-ylmethyl)-10H-acridin-9-one 
• 17386-23-1 1-(2-phenyl-thiazol-4-ylmethyl)-piperidine 
• 17386-21-9 2-phenyl-4-pyrrolidin-1-ylmethyl-thiazole 
• 78742-64-0 2-phenyl-4-(phenylsulfanyl-methyl)-thiazole 
• 854473-16-8 acetic acid-(2-phenyl-thiazol-4-ylmethyl ester) 
• 165736-03-8 (2-phenylthiazol-4-yl)methanamine 

Relevant articles and documents

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.

Structural and Activity Relationships of 6-Sulfonyl-8-Nitrobenzothiazinones as Antitubercular Agents

The benzothiazinone (BTZ) scaffold compound PBTZ169 kills Mycobacterium tuberculosis by inhibiting the essential flavoenzyme DprE1, consequently blocking the synthesis of the cell wall component arabinans. While extraordinarily potent against M. tuberculosis with a minimum inhibitory concentration (MIC) less than 0.2 ng/mL, its low aqueous solubility and bioavailability issues need to be addressed. Here, we designed and synthesized a series of 6-methanesulfonyl substituted BTZ analogues; further exploration introduced five-member aromatic heterocycles as linkers to attach an aryl group as the side chain. Our work led to the discovery of a number of BTZ derived compounds with potent antitubercular activity. The optimized compounds 6 and 38 exhibited MIC 47 and 30 nM, respectively. Compared to PBTZ169, both compounds displayed increased aqueous solubility and higher stability in human liver microsomes. This study suggested that an alternative side-chain modification strategy could be implemented to improve the druglike properties of the BTZ-based compounds.

Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2-phenylthiazole or oxazole skeletons

A series of novel pyridazinone derivatives were designed and synthesized by replacing 4-(tert-butyl)phenyl moiety of pyridaben with 2-phenylthiazole or oxazole fragments via activity substructure connecting approach. The structures of all target compounds were characterized through NMR, MS, and elemental analysis. Bioassay results exhibit that most compounds showed potent bioactivities against Aphis fabae, Tetranychus urticae, Erysiphe graminis, and/or Puccinia polysora. Among the newly synthesized compounds, 2-(tert-butyl)-4-chloro-5-(((2-phenylthiazol-4-yl)methyl)thio)pyridazin-3(2H)-one (12b) displays remarkable insecticidal activity against A fabae. Its LC50 value (2.73 mg/L) is better than that of pyridaben (5.46 mg/L), although inferior to that of imidacloprid (0.51 mg/L). In addition to its extraordinary insecticidal activity, compound 12b also exerts 96.9% fungicidal activities against P polysora at 500 mg/L in vivo, significantly superior to that of pyridaben (50.0%), while slightly lower than that of tebuconazole (100%). This article discusses the synthesis, bioassay results, and structure-activity relationship of this series of novel pyridazinone derivatives.