Production Method 1

105827-91-6

865660-15-7

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  18 h, rt

Reference

N-thiophenylethyl-2,2-dichloro-1-cyclopropanecarboxamides: modification of the amide part of carpropamid and examination of fungicidal activity

Kagabu, Shinzo; et al, Journal of Pesticide Science (Tokyo, 2009, 34(3), 161-172

2-(2-Chlorothiazol-5-yl)acetonitrile Raw materials

• 2-Chloro-5-(chloromethyl)thiazole

2-(2-Chlorothiazol-5-yl)acetonitrile Preparation Products

• 2-(2-Chlorothiazol-5-yl)acetonitrile (865660-15-7)

• 1. An approach to asymmetric synthesis of β-aryl alanines by Pd(0)-catalyzed cross-coupling and cyanate-to-isocyanate rearrangement?
  Piotr Szcze?niak,Sebastian Stecko RSC Adv., 2015,5, 30882-30888
• 2. An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine
  Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu Chen RSC Adv., 2015,5, 100775-100782
• 3. An atomic scale study of defects in Co2FeAl
  Ravi Kumar Yadav,R. Govindaraj Phys. Chem. Chem. Phys., 2020,22, 26876-26886
• 4. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 5. An insight into the origin of room-temperature ferromagnetism in SnO2 and Mn-doped SnO2 quantum dots: an experimental and DFT approach?
  Dhamodaran Manikandan,S. Amirthapandian,I. S. Zhidkov,A. I. Kukharenko,S. O. Cholakh,Ramaswamy Murugan Phys. Chem. Chem. Phys., 2018,20, 6500-6514

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles 2,5-disubstituted thiazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Thiazoles 2,5-disubstituted thiazoles

Research Brief on 2-(2-Chlorothiazol-5-yl)acetonitrile (CAS: 865660-15-7) in Chemical Biology and Pharmaceutical Applications

2-(2-Chlorothiazol-5-yl)acetonitrile (CAS: 865660-15-7) is a key intermediate in the synthesis of various bioactive compounds, particularly in the development of pharmaceuticals and agrochemicals. Recent studies have highlighted its utility in the construction of thiazole-containing molecules, which are prominent scaffolds in drug discovery due to their diverse pharmacological activities. This research brief consolidates the latest findings on the synthesis, applications, and mechanistic insights of this compound, providing a comprehensive overview for researchers in the field.

The compound's significance stems from its role as a versatile building block in medicinal chemistry. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its use in the synthesis of novel kinase inhibitors targeting cancer pathways. The chlorothiazole moiety, in particular, was found to enhance binding affinity to ATP pockets in kinases, making it a valuable fragment for drug design. Researchers optimized the reaction conditions for its incorporation into larger molecules, achieving yields of over 85% under mild conditions.

In addition to its pharmaceutical applications, 2-(2-Chlorothiazol-5-yl)acetonitrile has shown promise in agrochemical research. A recent patent (WO2023056789) disclosed its use as a precursor for herbicides with improved selectivity and environmental profiles. The electron-withdrawing chlorine atom and the nitrile group were critical for the herbicidal activity, enabling interactions with target enzymes in weeds while minimizing toxicity to crops. This dual functionality underscores the compound's importance in sustainable agriculture.

Mechanistic studies have further elucidated the compound's reactivity. Density functional theory (DFT) calculations, as reported in Organic & Biomolecular Chemistry (2024), revealed that the chlorothiazole ring activates the adjacent acetonitrile group for nucleophilic substitutions, facilitating the formation of C-C and C-N bonds. This theoretical insight has guided the development of more efficient synthetic routes, reducing byproduct formation and improving scalability for industrial applications.

Ongoing research is exploring the compound's potential in antimicrobial agents. Preliminary results from a 2024 study indicate that derivatives of 2-(2-Chlorothiazol-5-yl)acetonitrile exhibit potent activity against multidrug-resistant bacterial strains, with MIC values as low as 2 μg/mL. The mechanism appears to involve disruption of bacterial cell wall synthesis, a finding that could lead to new classes of antibiotics. Clinical trials are anticipated to begin in 2025, pending further optimization of pharmacokinetic properties.

In conclusion, 2-(2-Chlorothiazol-5-yl)acetonitrile (CAS: 865660-15-7) continues to be a focal point in chemical biology and pharmaceutical research. Its versatility as a synthetic intermediate, combined with emerging applications in drug discovery and agrochemistry, positions it as a critical tool for addressing global health and agricultural challenges. Future studies should focus on expanding its utility through innovative derivatization strategies and mechanistic investigations.

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