4994-13-2

Usage

Uses

Used in Chemical Industry:
4-Methylcyclohexanoneoxime is used as a stabilizer and inhibitor for its ability to prevent the corrosion of metals, particularly copper and its alloys, thus protecting them from degradation and extending their service life.
Used in Chemical Synthesis:
4-Methylcyclohexanoneoxime is used as a chemical intermediate in the production of other compounds, contributing to the synthesis of various organic and industrial chemicals.
Used in Organic Synthesis Reactions:
4-Methylcyclohexanoneoxime is used as a chemical reagent in a range of organic synthesis reactions, facilitating the creation of new compounds and materials for various applications.

InChI:InChI=1/C7H13NO/c1-6-2-4-7(8-9)5-3-6/h6,9H,2-5H2,1H3/b8-7-

Upstream product

• 82166-21-0 methyl cyclohexane 
• 589-92-4 1-methylcyclohexan-4-one 
• 6321-23-9 4-methylcyclohexylamine 

Downstream Products

• 591-47-9 4-methylcyclohexene 
• 2210-07-3 5-methyl-azepan-2-one 
• 2523-55-9 trans-4-methylcyclohexanamine 
• 16603-48-8 1-(hydroxyamino)-4-methylcyclohexanecarbonitrile 
• 128925-60-0 C₁₄H₁₇NO₂ 
• 128925-60-0 C₁₄H₁₇NO₂ 
• 172847-47-1 C₁₉H₂₂NOP 
• 78426-90-1 2-acetoxy-4-methylcyclohexanone 
• 75413-13-7 2,6-dimethyl-4,5,6,7-tetrahydro benzoxazole 
• 75230-61-4 Acetic acid 2-diacetylamino-5-methyl-cyclohex-1-enyl ester 
• 75230-60-3 Acetic acid 2-diacetylamino-5-methyl-cyclohex-2-enyl ester 
• 2523-56-0 cis-4-methylcyclohexanamine 
• 6321-23-9 4-methylcyclohexylamine 
• 84518-71-8 4,4'-dimethyldicyclohexylamine 

Relevant academic research and scientific papers

Oxidation of primary amines to oximes with molecular oxygen using 1,1-diphenyl-2-picrylhydrazyl and WO3/Al2O3 as catalysts

The oxidative transformation of primary amines to their corresponding oximes proceeds with high efficiency under molecular oxygen diluted with molecular nitrogen (O2/N2 = 7/93 v/v, 5 MPa) in the presence of the catalysts 1,1-diphenyl-2-picrylhydrazyl (DPPH) and tungusten oxide/alumina (WO3/Al2O3). The method is environmentally benign, because the reaction requires only molecular oxygen as the terminal oxidant and gives water as a side product. Various alicyclic amines and aliphatic amines can be converted to their corresponding oximes in excellent yields. It is noteworthy that the oxidative transformation of primary amines proceeds chemoselectively in the presence of other functional groups. The key step of the present oxidation is a fast electron transfer from the primary amine to DPPH followed by proton transfer to give the α-aminoalkyl radical intermediate, which undergoes reaction with molecular oxygen and hydrogen abstraction to give α-aminoalkyl hydroperoxide. Subsequent reaction of the peroxide with WO3/Al2O3 gives oximes. The aerobic oxidation of secondary amines gives the corresponding nitrones. Aerobic oxidative transformation of cyclohexylamines to cyclohexanone oximes is important as a method for industrial production of ε-caprolactam, a raw material for Nylon 6.

Aerobic oxidation of primary amines to oximes catalyzed by DPPH and WO 3/Al2O3

(Chemical Equation Presented) Catalytic teamwork: Aerobic oxidation of primary amines to the corresponding oximes proceeds highly efficiently in the presence of the catalysts 1,1-diphenyl-2-picrylhydrazyl (DPPH) and WO 3/Al2O3 under mild conditions (see scheme). This new method is both selective and environmentally benign.

Chlorination of oximes with aqueous H2O2/HCl system: Facile synthesis of gem-chloronitroso- and gem-chloronitroalkanes, gem-chloronitroso- and gem-chloronitrocycloalkanes

Chlorination of cyclic and linear ketone oximes with aqueous H 2O2/HCl in a two-phase dichloromethane-water system selectively affords gem-chloronitroso compounds in yields of up to 94%. One-pot oxidation of the resulting gem-chloronitroso compounds with peracetic acid, prepared in situ, gives gem-chloronitroalkanes and cycloalkanes in yields of up to 82%. The advantages of the method are that it is facile and environmentally benign and does not require gaseous chlorine. Georg Thieme Verlag Stuttgart.

Synthesis of amides with anti-inflammatory and analgesic activities

A series of N-Aroyl-cyclohexyl- and cyclohexenylamides 3- or 4- methylsubstituted were synthesized and evaluated for their anti-inflammatory and analgesic potencies, and gastrointestinal irritation liability. One compound, N-benzoyl-4-methyl-cyclohexylamide 6a, possessed an anti- inflammatory activity comparable to that of indomethacin.

Stereoselective hydride reductions of cyclic N-diphenylphosphinyl imines. Highly diastereoselective syntheses of protected primary amines

Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.