583-60-8

Basic information

• Product Name: 2-Methylcyclohexanone
• Synonyms: alpha-methylcyclohexanone[qr];methylanon[qr];o-Methylcyclohexanon;o-methylcyclohexanone[qr];sextonb[qr];2-METHYLCYCLOHEXANONE;FEMA 3946;METHYLCYCLOHEXANONE, 2-
• CAS NO: 583-60-8
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.17
• EINECS: 209-513-6
• Mol File: 583-60-8.mol
• Article Data: 366

Chemical Properties

• Melting Point: -14 °C
• Boiling Point: 162-163 °C(lit.)
• Flash Point: 116 °F
• Appearance: Clear colorless to very slightly yellow/Liquid
• Density: 0.924 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.04mmHg at 25°C
• Refractive Index: n20/D 1.448(lit.)
• Storage Temp.: Flammables area
• Solubility: Soluble in alcohol, ether (Weast, 1986), and many other polar organic solvents including cyclohexanone.
• Explosive Limit: 1.2%(V)
• Water Solubility: Insoluble in water. Soluble in methanol and diethyl ether.
• BRN: 506751
• CAS DataBase Reference: 2-Methylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylcyclohexanone(583-60-8)
• EPA Substance Registry System: 2-Methylcyclohexanone(583-60-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20-20/21/22
• Safety Statements: 25-36/37
• RIDADR: UN 2297 3/PG 3
• WGK Germany: 1
• RTECS: GW1750000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 583-60-8(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 583-60-8 differently. You can refer to the following data:
1. CLEAR COLOURLESS TO VERY SLIGHTLY YELLOW LIQUID
2. o-Methylcyclohexanone is a colorless liquid with a weak peppermint-like odor (also reported to be acetone-like).
3. 2-Methylcyclohexanone has a weak, peppermint odor and burning sensation

Physical properties

Colorless liquid with a weak, peppermint-like odor.

Occurrence

Reported found in cockroaches as attractant pheromone; not reported found in natural foods

Uses

Different sources of media describe the Uses of 583-60-8 differently. You can refer to the following data:
1. Solvent; rust remover
2. o-Methyl cyclohexanone is used as a solventfor varnishes, lacquers, and plastics; and asa rust remover.
3. 2-Methylcyclohexanone can be used as solvent, lacquers.

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

General Description

A water-white to pale yellow liquid with an acetone-like odor. Less dense than water. Vapors heavier than air. Flash point near 135°F. May be toxic by ingestion. Used as a solvent.

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

Different sources of media describe the Health Hazard of 583-60-8 differently. You can refer to the following data:
1. May cause irritation of the eyes, nose and throat. Prolonged or repeated contact may cause dermatitis.
2. 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 
• 108-94-1 cyclohexanone 
• 95-92-1 oxalic acid diethyl ester 
• 1713-33-3 1,2-epoxy-1-methylcyclohexane 
• 591-49-1 1-methylcyclohex-1-ene 
• 23115-33-5 Bis(trimethylsilyl) peroxomonosulfate 
• 1122-26-5 2-methylcyclohexanone oxime 
• 36851-77-1 6-bromo-hex-2-ene 
• 201230-82-2 carbon monoxide 
• 583-59-5 2-Methylcyclohexanol 
• 6004-60-0 1-cyclopentylethanone 
• 19980-35-9 1-trimethylsilyloxy-2-methyl-1-cyclohexene 

Downstream Products

• 5049-51-4 6-methyl-1-pyrrolidino-1-cyclohexene 
• 132982-81-1 2,2'-dimethyl-2,2'-methanediyl-bis-cyclohexanone 
• 56053-07-7 (+/-)-2-((Ξ)-furfurylidene)-6-methyl-cyclohexanone 
• 854435-34-0 1-(2-chloro-phenyl)-2-methyl-cyclohexanol 
• 101869-70-9 Opt_.-inakt. 1-Hydroxy-2-methyl-1-hydroxymethyl-cyclohexan 
• 7443-70-1 cis-2-methylcyclohexanol 
• 19879-12-0 cis-1,2-dimethylcyclohexanol 
• 19879-11-9 1,2-dimethylcyclohexanol 
• 24580-48-1 Opt_.-inakt. 2-Hydroxy-1-methyl-2-propyl-cyclohexan 
• 109938-87-6 4-(2-methyl-cyclohexenyl)-biphenyl 
• 51650-55-6 Opt_.-inakt. 2-Hydroxy-1-methyl-2-pentyl-cyclohexan 
• 15564-30-4 cis-1-ethynyl-2-methylcyclohexan-ol 
• 15564-30-4 cis-1-Ethinyl-2-methyl-1-cyclohexanol 
• 7443-52-9 (+/-)-trans-2-methylcyclohexanol 

Relevant articles and documents

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

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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.

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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.

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)

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

Synthesis of Chiral Amines via a Bi-Enzymatic Cascade Using an Ene-Reductase and Amine Dehydrogenase

Access to chiral amines with more than one stereocentre remains challenging, although an increasing number of methods are emerging. Here we developed a proof-of-concept bi-enzymatic cascade, consisting of an ene reductase and amine dehydrogenase (AmDH), to afford chiral diastereomerically enriched amines in one pot. The asymmetric reduction of unsaturated ketones and aldehydes by ene reductases from the Old Yellow Enzyme family (OYE) was adapted to reaction conditions for the reductive amination by amine dehydrogenases. By studying the substrate profiles of both reported biocatalysts, thirteen unsaturated carbonyl substrates were assayed against the best duo OYE/AmDH. Low (5 %) to high (97 %) conversion rates were obtained with enantiomeric and diastereomeric excess of up to 99 %. We expect our established bi-enzymatic cascade to allow access to chiral amines with both high enantiomeric and diastereomeric excess from varying alkene substrates depending on the combination of enzymes.

Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.