4994-13-2

Basic information

• Product Name: 4-Methylcyclohexanoneoxime
• Synonyms: p-Methylcyclohexanone oxime;cyclohexanone, 4-methyl-, oxime
• CAS NO: 4994-13-2
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.19
• Mol File: 4994-13-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 218.1°Cat760mmHg
• Flash Point: 117.5°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 0.0486mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: 4-Methylcyclohexanoneoxime(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylcyclohexanoneoxime(4994-13-2)
• EPA Substance Registry System: 4-Methylcyclohexanoneoxime(4994-13-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 4994-13-2(Hazardous Substances Data)

Usage

General Description

4-Methylcyclohexanoneoxime, also known as MCHOX, is an organic compound that is commonly used as a stabilizer and inhibitor in industrial settings. It is a colorless, crystalline solid with a melting point of 86-90°C. 4-Methylcyclohexanoneoxime is known for its ability to inhibit the corrosion of metals, particularly copper and its alloys. It is also used as a chemical intermediate in the production of other compounds. In addition, it is used as a chemical reagent in various organic synthesis reactions. 4-Methylcyclohexanoneoxime is considered to have low toxicity and is not known to be a significant environmental or health hazard.

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 articles and documents

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.

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.

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.