583-60-8

Usage

Uses

Used in Chemical Industry:
2-Methylcyclohexanone is used as a solvent for various applications, including varnishes, lacquers, and plastics. Its solubility properties make it a versatile component in the formulation of these materials.
Used as a Rust Remover:
2-Methylcyclohexanone is also utilized as a rust remover due to its ability to dissolve and break down rust particles, making it easier to clean and maintain metal surfaces.

Preparation

From cyclohexanone by treatment with a base and then with methyl iodide

Production Methods

2-Methylcyclohexanone is manufactured by the catalytic hydrogenation of o-cresol or by the dehydrogenation of o-methylcyclohexanol. Methylcyclohexanones are used in small amounts as general purpose solvents for cellulose-based finishes and coatings.

Synthesis Reference(s)

Journal of the American Chemical Society, 108, p. 304, 1986 DOI: 10.1021/ja00262a025Synthetic Communications, 8, p. 9, 1978 DOI: 10.1080/00397917808062176Synthesis, p. 611, 1976 DOI: 10.1055/s-1976-24139

Air & Water Reactions

Flammable. Slightly soluble in water.

Reactivity Profile

Contact with strong oxidizers may cause fires and explosions [USCG, 1999].

Hazard

Moderate fire risk. Toxic by ingestion,inhalation, and skin absorption. Eye and upper res-piratory tract irritant, and central nervous systemimpairment.

Health Hazard

May cause irritation of the eyes, nose and throat. Prolonged or repeated contact may cause dermatitis.

Health Hazard

o-Methyl cyclohexanone is a mildly toxiccompound. Any health hazard from inhalingits vapors is low. Its vapors at highconcentrations in air can be irritating to theeyes, nose, and throat. Ingestion of the liquidcan cause sleepiness. Toxicity studies on animalssuggest that methyl cyclohexanone maycause an adverse effect on the lungs, kidney,and liver. An intravenous administration of270 mg/kg was lethal to mice.LD50 value, intraperitoneal (mice): 200mg/kg.

Flammability and Explosibility

Flammable

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion and skin contact. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Methylcyclohexanone is used as a solvent in making varnish, plastics, and as a rust remover. Also used in the leather industry.

Shipping

UN2297 Methylcyclohexanone, Hazard Class: 3; Labels: 3-Flammable liquid.

Incompatibilities

Vapors may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Contact with peroxides may form unstable heat- and shock-sensitive explosives

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed

InChI:InChI=1/C7H12O/c1-6-4-2-3-5-7(6)8/h6H,2-5H2,1H3/t6-/m0/s1

Upstream product

• 1117-96-0 Diazoethan 
• 60-29-7 diethyl ether 
• 120-92-3 cyclopentanone 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 74-88-4 methyl iodide 
• 93-59-4 Perbenzoic acid 
• 2311-91-3 monoperoxyphthalic acid 
• 591-49-1 1-methylcyclohex-1-ene 
• 64-17-5 ethanol 
• 933-35-7 (+/-)-1-hydroxy-2c-methyl-cyclohexane-r-carbonitrile 
• 855210-00-3 2-methyl-7,9-dioxo-decanoic acid ethyl ester 
• 141-52-6 sodium ethanolate 
• 583-59-5 2-Methylcyclohexanol 
• 2808-75-5 2-methyl-1-methylenecyclohexane 

Downstream Products

• 5049-51-4 6-methyl-1-pyrrolidino-1-cyclohexene 
• 56053-07-7 (+/-)-2-((Ξ)-furfurylidene)-6-methyl-cyclohexanone 
• 38382-68-2 (+/-)-2-methyl-6-((Ξ)-[2]thienylmethylene)-cyclohexanone 
• 102370-18-3 1-ethyl-2-methyl-cyclohexanol 
• 13757-31-8 1-Butyl-2-methyl-cyclohexanol 
• 854712-37-1 2,2'-dimethyl-1,1'-ethynediyl-bis-cyclohexanol 
• 103095-86-9 5-(2-methyl-cyclohexyLiDene)-2-thioxo-thiazolidin-4-one 
• 15885-63-9 1-Methyl-2-isonicotinoylhydrazono-cyclohexan 
• 1194-91-8 3-methyl-2-oxo-cyclohexanecarbaldehyde 
• 76505-82-3 3-hydroxy-3-(3-methyl-2-oxo-cyclohexyl)-indolin-2-one 
• 1196-73-2 1-acetoxy-2-methylcyclohexene 
• 24785-76-0 2-benzyl-6-methylcyclohexan-1-one 
• 1206-21-9 2-benzyl-2-methyl-cyclohexanone 
• 1208-47-5 6-benzylidene-2-methylcyclohexan-1-one 

Relevant academic research and scientific papers

Activation of hydrogen peroxide by ionic liquids: Mechanistic studies and application in the epoxidation of olefins

Imidazolium-based ionic liquids that contain perrhenate anions are very efficient reaction media for the epoxidation of olefins with H2O 2 as an oxidant, thus affording cyclooctene in almost quantitative yields. The mechanism of this reaction does not follow the usual pathway through peroxo complexes, as is the case with long-known molecular transition-metal catalysts. By using in situ Raman, FTIR, and NMR spectroscopy and DFT calculations, we have shown that the formation of hydrogen bonds between the oxidant and perrhenate activates the oxidant, thereby leading to the transfer of an oxygen atom onto the olefin demonstrating the special features of an ionic liquid as a reaction environment. The influence of the imidazolium cation and the oxidant (aqueous H2O2, urea hydrogen peroxide, and tert-butyl hydrogen peroxide) on the efficiency of the epoxidation of cis-cyclooctene were examined. Other olefinic substrates were also used in this study and they exhibited good yields of the corresponding epoxides. This report shows the potential of using simple complexes or salts for the activation of hydrogen peroxide, owing to the interactions between the solvent medium and the active complex. Copyright

Pronounced catalytic activity of manganese(III) - Schiff base complexes in the oxidation of alcohols by tetrabutylammonium peroxomonosulfate

A novel and practical catalytic method for efficient and highly selective oxidation of a wide range of benzylic, allylic, aliphatic, primary, and secondary alcohols to the corresponding aldehydes and ketones using tetrabutylammonium peroxomonosulfate cata

RHODIUM-CATALYZED STEREOSELECTIVE DEHYDROGENATION OF CIS- AND -TRANS-METHYLCYCLOHEXANOLS BY MOLECULAR OXYGEN

Methylcyclohexanols were dehydrogenated stereoselectively by rhodium phosphine catalyst and molecular oxygen.The less stable stereoisomers were consumed preferentially.

Two new silver(I) complexes with 2,4,6-tris(2-pyridyl)-1,3,5-triazine (tptz): Preparation, characterization, crystal structure and alcohol oxidation activity in the presence of oxone

Two new silver(I) complexes ((tptz)Ag2(NO3) 2 and [Ag5(tptz)4](NO3)5) with 2,4,6-tris(2-pyridyl)-1,3,5-triazine (tptz) have been synthesized and characterized by X-ray diffraction, elemental analysis, 1H NMR, IR, fluorescence, UV-Vis spectroscopy and electrochemistry. Oxidation of alcohols to their corresponding aldehydes and ketones was conducted with one of the Ag complexes as a catalyst, soluble enough in organic solvent, using oxone (2KHSO5·KHSO4·K2SO4) as an oxidant under biphasic reaction conditions (CH2Cl 2/H2O) and tetra-n-butylammonium bromide as phase transfer agent under air at room temperature.

Calcined layered double hydroxides as basic heterogeneous catalysts for the oppenauer oxidation of alcohols

The oxidation of various alcohols with a ketone was carried out over a series of calcined layered double hydroxides, producing corresponding ketones in a batch reaction system. From the observed results it was found that the layered double hydroxide, Mg(I

STEREOCHEMICAL EFFECTS IN THE GAS-PHASE PINACOL REARRANGEMENT OF CIS- AND TRANS-1-METHYLCYCLOHEXANE-1,2-DIOL.

The gas-phase pinacol rearrangement of cis and trans-1-methyl-1,2-cyclohexanediols, promoted by D3(+) and CnH5(+) (n= 1,2), was studied by the radiolytic method in the pressure range 100-760 Torr.Under all conditions, 2-methyl-cyclohexanone is the predominant product, arising from both substrates via different pinacol rearrangements and successive fast isomerisation of the corresponding primary intermediates, e,g, O-protonated 1-methyl-1-cyclopentanecarboxaldehyde.This conclusion is based from kinetic analysis of competition experiments with pinacol as reference substrate, carried out at high pressure (760 Torr) with or without added base (NMe3, 3 Torr), showing that the pinacol rearrngement rates are markedly dependent on the stereochemical features of the diol.Accordingly, the trans diol rearranges more rapidly than the cis isomer, which in turn isomerizes faster than pinacol, indicating that anti-periplanar CH2 migration to the vicinal tertiary C-OH2(+) center in trans (k2) is over five times faster than H migration in cis (k3).Analysis of the relative migrating ability of the different CH2 moieties in trans (k2 > k1) allowed exclusion of appreciable anchimeric assistance in these gas-phase pinacol rearrangements.The results are compared with revelant gas-phase data with those concerting the same substrates in acidic solution.

Carbon-carbon bond formation reactions of the iodomethane complex [Cp(dppe)Ru(ICH3)]PF6

The new iodomethane complex [Cp(dppe)-Ru(IMe)](CF3SO3) (1a) is formed by a new synthetic route, the reaction between methyl trifluoromethanesulfonate and Cp(dppe)RuI (dppe = 1,2-bis(diphenylphosphino)ethane). The hexafluorophosphate salt 1b reacts with a wide range of nucleophiles, including enamines and lithium enolates, affording C-methylation products. In the first reported case of carbon-carbon bond formation via a halocarbon complex, complex 1 regioselectively methylates 1-(N-pyrrolidino)cyclohexene producing 2-methylcyclohexanone in good yield, after hydrolysis. We also report the synthesis of a new haloarene complex and its equilibration with free iodomethane.

A new and highly effective method for catalytic oxidation of alcohols to the corresponding carbonyl compounds using the tris[(2-oxazolinyl)phenolato] manganese(III)/Oxone/n-Bu4NBr oxidation system

Oxone (2KHSO5·KHSO4·K 2SO4) in the presence of mer-tris[(2-oxazolinyl)phenolato] manganese(III), Mn(phox)3, as catalyst under biphasic reaction conditions (CH2Cl2/H2O)

Theoretical Prediction and Experimental Confirmation of Relative Stabilities of Isomeric Allyl Anions from Enamines and Vinyl Ethers

Relative stabilities of isomeric allyl anions from enamines and vinyl ethers are predicted in terms of the continuity-discontinuity of the orbital phase.The predictions are supported by ab initio molecular orbital calculations and confirmed by experiments on model compounds.

Reduction of nitrosoarene ligands in binuclear palladium(II) complexes

Reduction of the binuclear Pd11 complexes Pd2(OCOR)2(o-CH2C6H4-NO)2 (1) and Pd2(OCOR)2(o-PhN-C6H4-NO)2 (2) (where R = Me, C