64431-75-0

Basic information

• Product Name: Diazocyclohexane
• Synonyms: Diazocyclohexane
• CAS NO: 64431-75-0
• Molecular Weight: 110.159
• Mol File: 64431-75-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Diazocyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: Diazocyclohexane(64431-75-0)
• EPA Substance Registry System: Diazocyclohexane(64431-75-0)

Safety Data

• Hazardous Substances Data: 64431-75-0(Hazardous Substances Data)

Upstream product

• 6156-08-7 cyclohexanone hydrazone 
• 138723-92-9 2,2-dimethoxy-5,5-pentamethylene-1,3,4-Δ³-oxadiazoline 
• 4545-18-0 N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide 
• 80-30-8 N-cyclohexyl-p-toluenesulfonamide 
• 108-94-1 cyclohexanone 
• 33469-53-3 N-cyclohexyl-N-nitroso-toluene-4-sulfonamide 

Downstream Products

• 52867-48-8 (E)-2-(N-Cyclohexyl-N'-cyclohexylidene-hydrazino)-but-2-enedioic acid dimethyl ester 
• 2412-73-9 benzoic acid cyclohexyl ester 
• 32137-21-6 cyclohexylhydrazone of cyclohexanone 

Relevant articles and documents

Δ3-1,3,4-oxadiazolines: Photochemical precursors to diazoalkanes and sec-alkanediazonium ions in acidic solution

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Safe and Facile Access to Nonstabilized Diazoalkanes Using Continuous Flow Technology

Despite the high synthetic potential of nonstabilized diazo compounds, their utilization has always been hampered by stability, toxicity, and safety issues. The present method opens up access to the most reactive nonstabilized diazoalkanes. Among diazo compounds, nonstabilized alkyl diazo compounds are the least represented because of their propensity to degrade during preparation. The continuous flow oxidation process of hydrazones on a silver oxide column afforded an output stream of base- and metal-free pure diazo solution in dichloromethane. Starting from innocuous ketones and aldehydes, this methodology allows the production of a broad range of unprecedented diazoalkanes compounds in excellent yields, while highlighting their synthetic potential and the possibility of safe large-scale diazo production.

Diazo preparation via dehydrogenation of hydrazones with "activated" DMSO

We report that "activated" dimethyl sulfoxide efficiently dehydrogenates hydrazones to the respective diazo species at -78°C. Under optimized conditions, triethylamine hydrochloride is removed quantitatively by vacuum filtration to provide solutions of diazo compounds. Stable diazo species can be isolated in high yield, or alternatively, the direct treatment of these solutions with carboxylic acids provides esters.