2-Methylcyclohexanone

Base Information

• Chemical Name: 2-Methylcyclohexanone
• CAS No.: 583-60-8
• Deprecated CAS: 24965-84-2
• Molecular Formula: C7H12O
• Molecular Weight: 112.172
• Hs Code.: 29142200
• European Community (EC) Number: 209-513-6
• NSC Number: 524
• UN Number: 2297
• UNII: 56E8224ZFJ
• DSSTox Substance ID: DTXSID6052245
• Nikkaji Number: J3.301D
• Wikidata: Q20968563
• Pharos Ligand ID: TQ6TKXSS2GHS
• Metabolomics Workbench ID: 44936
• ChEMBL ID: CHEMBL1946183
• Mol file: 583-60-8.mol

Synonyms:2-methylcyclohexanone

Chemical Property of 2-Methylcyclohexanone

Chemical Property:

• Appearance/Colour: CLEAR COLOURLESS TO VERY SLIGHTLY YELLOW LIQUID
• Vapor Pressure: 2.04mmHg at 25°C
• Melting Point: -14 °C
• Refractive Index: n20/D 1.448(lit.)
• Boiling Point: 163.7 °C at 760 mmHg
• Flash Point: 45.9 °C
• PSA: 17.07000
• Density: 0.912 g/cm³
• LogP: 1.76560
• Storage Temp.: Flammables area
• Solubility.: Soluble in alcohol, ether (Weast, 1986), and many other polar organic solvents including cyclohexanone.
• Water Solubility.: Insoluble in water. Soluble in methanol and diethyl ether.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 112.088815002
• Heavy Atom Count: 8
• Complexity: 96.6
• Transport DOT Label: Flammable Liquid

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Methylcyclohexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-20-20/21/22
• Safety Statements: 25-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: CC1CCCCC1=O
• Physical properties: Colorless liquid with a weak, peppermint-like odor.
• Uses: Solvent; rust remover o-Methyl cyclohexanone is used as a solventfor varnishes, lacquers, and plastics; and asa rust remover. 2-Methylcyclohexanone can be used as solvent, lacquers.

Technology Process of 2-Methylcyclohexanone

There total 364 articles about 2-Methylcyclohexanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + methyl iodide (74-88-4) → 2,6-dimethylcyclohexanone (2816-57-1) + 2,2-dimethyl-cyclohexanone (1193-47-1) + 2-Methylcyclohexanone (583-60-8)

Guidance literature:

With manganese(II) bromide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hexamethyldisilazane; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1016/S0040-4039(00)60135-1

Reference yield: 16.0%

7-iodohept-1-en-3-one (139367-30-9) → 2-Methylcyclohexanone (583-60-8) + cycloheptanone (502-42-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; Heating;

DOI:10.1021/jo00057a039

Reference yield: 15.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + methyl iodide (74-88-4) → 2,2-dimethyl-cyclohexanone (1193-47-1) + 2-Methylcyclohexanone (583-60-8)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 50 ℃; for 2h;

upstream raw materials:

Diazoethan

diethyl ether

cyclopentanone

1-(1-Cyclohexen-1-yl)pyrrolidine

Downstream raw materials:

6-methyl-1-pyrrolidino-1-cyclohexene

2,2'-dimethyl-2,2'-methanediyl-bis-cyclohexanone

(+/-)-2-((Ξ)-furfurylidene)-6-methyl-cyclohexanone

1-but-3-en-1-ynyl-2-methyl-cyclohexanol

Refernces

• 1、 Rezaeifard, Abdolreza,Jafarpour, Maasoumeh,Nasseri, Mohammad Ali,Haddad, Reza. "Pronounced catalytic activity of manganese(III) - Schiff base complexes in the oxidation of alcohols by tetrabutylammonium peroxomonosulfate". . p. 711 - 717. Retrieved 2010.
• 2、 Okamoto, Tadashi,Sasaki, Ken,Oka, Shinzaburo. "RHODIUM-CATALYZED STEREOSELECTIVE DEHYDROGENATION OF CIS- AND -TRANS-METHYLCYCLOHEXANOLS BY MOLECULAR OXYGEN". . p. 1247 - 1250. Retrieved 1984.
• 3、 Whitesell,Felman. "-". . p. 1663. Retrieved 1977.
• 4、 Raja, Thirumalaiswamy,Jyothi,Sreekumar,Talawar,Santhanalakshmi,Rao. "Calcined layered double hydroxides as basic heterogeneous catalysts for the oppenauer oxidation of alcohols". . p. 2117 - 2119. Retrieved 1999.
• 5、 Kulawiec, Robert J.,Crabtree, Robert H.. "Carbon-carbon bond formation reactions of the iodomethane complex [Cp(dppe)Ru(ICH3)]PF6". . p. 1891 - 1893. Retrieved 1988.
• 6、 Inagaki, Satoshi,Iwase, Koji,Goto, Naomi. "Theoretical Prediction and Experimental Confirmation of Relative Stabilities of Isomeric Allyl Anions from Enamines and Vinyl Ethers". . p. 2019 - 2022. Retrieved 1984.
• 7、 Banerjee, Sridhar,Haukka, Matti,Hossain, Md. Kamal,Huelsmann, Ricardo Dagnoni,Martendal, Edmar,Munshi, Sandip,Nordlander, Ebbe,Paine, Tapan K.,Peralta, Rosely,Singh, Reena,Sinha, Arup,Valiati, Andrei Felipe,Wendt, Ola F.,Xavier, Fernando,Yiga, Solomon. "Hydrogen-atom and oxygen-atom transfer reactivities of iron(". supporting information. p. 870 - 884. Retrieved 2022/02/01.
• 8、 Martin, Teo,Galeotti, Marco,Salamone, Michela,Liu, Fengjiao,Yu, Yanmin,Duan, Meng,Houk,Bietti, Massimo. "Deciphering Reactivity and Selectivity Patterns in Aliphatic C-H Bond Oxygenation of Cyclopentane and Cyclohexane Derivatives". supporting information. p. 9925 - 9937. Retrieved 2021/06/30.