20258-07-5

Usage

Uses

Used in Agricultural Industry:
CYCLOHEXYL N-CYCLOHEXYLCARBAMATE is used as an insecticidal agent for controlling a wide range of insect pests in various crops. It is valued for its effectiveness in managing insect infestations that can damage or destroy crops, thereby protecting agricultural yields and ensuring food security.
The application reason for using CYCLOHEXYL N-CYCLOHEXYLCARBAMATE in this context is its ability to interfere with the insects' nervous systems, causing paralysis and death, which helps in reducing the impact of pests on crop health and productivity. Its relatively low toxicity to humans and non-target species makes it a preferred choice in integrated pest management strategies, aiming to balance effective pest control with environmental and human safety.

Upstream product

• 1122-56-1 cyclohexylcarboxamide 
• 108-93-0 cyclohexanol 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 3173-53-3 Cyclohexyl isocyanate 
• 766-93-8 N-cyclohexylformamide 
• 108-91-8 cyclohexylamine 
• 13248-54-9 cyclohexyl chloroformate 

Relevant academic research and scientific papers

Dehydrogenative Synthesis of Carbamates from Formamides and Alcohols Using a Pincer-Supported Iron Catalyst

We report that the pincer-ligated iron complex (iPrPNP)Fe(H)(CO) [1, iPrPNP- = N(CH2CH2PiPr2)2-] is an active catalyst for the dehydrogenative synthesis of N-alkyl- and N-aryl-substituted carbamates from formamides and alcohols. The reaction is compatible with industrially relevant N-alkyl formamides, as well as N-aryl formamides, and 1°, 2°, and benzylic alcohols. Mechanistic studies indicate that the first step in the reaction is the dehydrogenation of the formamide to a transient isocyanate by 1. The isocyanate then reacts with the alcohol to generate the carbamate. However, in a competing reaction, the isocyanate undergoes a reversible cycloaddition with 1 to generate an off-cycle species, which is the resting state in catalysis. Stoichiometric experiments indicate that high temperatures are required in catalysis to facilitate the release of the isocyanate from the cycloaddition product. We also identified several other off-cycle processes that occur in catalysis, such as the 1,2-addition of the formamide or alcohol substrate across the Fe-N bond of 1. It has already been demonstrated that the transient isocyanate generated from dehydrogenation of the formamide can be trapped with amines to form ureas and, in principle, the isocyanate could also be trapped with thiols to form thiocarbamates. Competition experiments indicate that trapping of the transient isocyanate with amines to produce ureas is faster than trapping with an alcohol to produce carbamates and thus ureas can be formed selectively in the presence of alcohols. In contrast, thiols bind irreversibly to the iron catalyst through 1,2 addition across the Fe-N bond of 1, and it is not possible to produce thiocarbamates. Overall, our mechanistic studies provide general guidelines for facilitating dehydrogenative coupling reactions using 1 and related catalysts.

HYDROGENATION OF N-ARYL CARBAMATES TO N-ALICYCLIC CARBAMATES.

An economical, high-yield process is developed for the preparation of pure N-alicyclic carbamates by the rhodium-catalyzed hydrogenation of the corresponding N-aryl carbamates. The N-aryl carbamates are obtained by the simple reaction of low-cost aromatic