Formyldiazomethane (CHOCHN₂) and difluoromethyldiazomethane (CHF₂CHN₂) are highly reactive, low-molecular-weight compounds widely used to introduce difluoromethyl or aldehyde groups into organic molecules. Despite their value, these functionalized diazomethane derivatives pose significant safety risks due to their gaseous state, volatility, toxicity, and explosiveness under standard conditions. Existing production methods require handling explosive diazo solutions, further increasing experimental hazards.

Innovative Solution: DFHZ-Tfs Reagent

Building on the success of the trifluoromethyldiazomethane reagent (TFHZ-Tfs, Cat. No. 9025326), Professor Bi Xihe’s research group at Northeast Normal University has developed a new, safer alternative:

  • Difluoroacetaldehyde N-o-trifluorotoluenesulfonylhydrazone (DFHZ-Tfs, Cat. No. 9171852)

Exclusively supplied by J&K Scientific, DFHZ-Tfs eliminates the need for direct handling of hazardous reagents, significantly enhancing safety in the lab.

Key Advantages of DFHZ-Tfs:

  • In Situ Generation of Diazomethanes:
    • Difluoromethyldiazomethane (in anhydrous organic solvents)
    • Formyldiazomethane (in solution systems)
    • Easily switch between products by changing the reaction solvent.
  • Safer Handling:
    • No need to work directly with explosive diazo solutions.
    • Minimizes safety risks in diazomethane synthesis and usage.
  • High Efficiency and Versatility:
    • High yields and high selectivity in critical transformations.
    • Ideal for cyclopropanation and Doyle-Kirmse reactions (Figure 3).

Broad Application Potential

This novel reagent opens up new opportunities for safer and more efficient organic synthesis, making it an essential tool for researchers working with highly reactive functional groups.

Figure 1. Difluoroacetaldehyde N-trifluoromethylbenzenesulfonylhydrazone(DFHZ-Tfs, Cat. No. 9171852)Characteristics

Figure 2. DFHZ-Tfs generates difluoromethyldiazomethane under anhydrous reaction conditions; formsyldiazomethane under aqueous conditions [1][1]

Reference

  1. Yongquan Ning, Xinyu Zhang, Yi Gai, Yuanqing Dong, Paramasivam Sivaguru, Yingying Wang, Bhoomireddy Rajendra Prasad Reddy, Giuseppe Zanoni, Xihe Bi*, Angew. Chem. Int. Ed. 2020, 59, 6473–6481.

 

By 向阳 翟

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