4-Methylcyclohexanone

Base Information

• Chemical Name: 4-Methylcyclohexanone
• CAS No.: 589-92-4
• Molecular Formula: C7H12O
• Molecular Weight: 112.172
• Hs Code.: 29142200
• European Community (EC) Number: 209-665-3,215-556-1
• NSC Number: 3816
• UN Number: 2297
• UNII: 0L1R78K79S
• DSSTox Substance ID: DTXSID5060435
• Nikkaji Number: J1.213K
• Wikidata: Q22138343
• Metabolomics Workbench ID: 44937
• Mol file: 589-92-4.mol

Synonyms:4-Methyl-1-cyclohexanone;4-07-00-00044 (Beilstein Handbook Reference);NSC 3816;AI3-15916;BRN 0506746;Methyl-4 cyclohexanone-1;Methyl-4 cyclohexanone-1 [French];Cyclohexanone, 4-methyl-;

Chemical Property of 4-Methylcyclohexanone

Chemical Property:

• Appearance/Colour: Clear slightly yellow liquid.
• Vapor Pressure: 1.5mmHg at 25°C
• Melting Point: -41 ºC
• Refractive Index: n20/D 1.4443(lit.)
• Boiling Point: 170 ºC at 760 mmHg
• Flash Point: 45.9 ºC
• PSA: 17.07000
• Density: 0.912 g/cm³
• LogP: 1.76560
• Storage Temp.: Flammables area
• Water Solubility.: Not miscible in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 112.088815002
• Heavy Atom Count: 8
• Complexity: 86.6

Purity/Quality:

99% ^*data from raw suppliers

4-Methylcyclohexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn,Xi
• Statements: 10-22-20/21/22-2017/10/22
• Safety Statements: 16-36-36/37-23

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: CC1CCC(=O)CC1
• Description: 4-methylcyclohexanone is a colorless liquid with a musty animalistic odor. It is used as a food additive.
• Uses: Intermediates of Liquid Crystals 4-Methylcyclohexanone was used in the synthesis of the pinguisane-type sesquiterpenoid acutifolone A, in racemic form. It is used as intermediates of CCNU and it can be also be used as a solvent.

Technology Process of 4-Methylcyclohexanone

There total 120 articles about 4-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:

p-methylcyclohexanol (589-91-3) + acetophenone (98-86-2) → 1-Phenylethanol (98-85-1,13323-81-4) + 1-methylcyclohexan-4-one (589-92-4)

Guidance literature:

potassium hydroxide; Ru(CF₃CO₂)CO(PPh₃)2; at 140 ℃; for 6h; Equilibrium constant;

Reference yield:

methyl cyclohexane (82166-21-0) → 1-Methylcyclohexanol (590-67-0) + trans-4-methylcyclohexan-1-ol (7731-29-5) + cis-4-methylcyclohexanol (7731-28-4) + (+/-)-trans-2-methylcyclohexanol (7443-52-9) + cis-2-methylcyclohexanol (7443-70-1) + rac-trans-3-methylcyclohexanol (7443-55-2) + cis-3-methylcyclohexanol (5454-79-5) + 1-methylcyclohexan-4-one (589-92-4) + 2-Methylcyclohexanone (583-60-8) + cyclohexylmethyl alcohol (100-49-2) + cyclohexanecarbaldehyde (2043-61-0) + 3-Methylcyclohexanone (591-24-2,625-96-7)

Guidance literature:

With C₂₂H₁₇BClF₉N₆NiO₃; at 70 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ja4020277

Reference yield:

methyl cyclohexane (82166-21-0) → 2-Methylcyclohexanol (583-59-5) + 1-methylcyclohexan-4-one (589-92-4) + 2-Methylcyclohexanone (583-60-8) + cyclohexylmethyl alcohol (100-49-2) + cyclohexanecarbaldehyde (2043-61-0) + 3-Methylcyclohexanone (591-24-2,625-96-7)

Guidance literature:

With peracetic acid; Mn₂O₃(N,N',N''-trimethyl-1,4,7-triazacyclononane)2; dihydrogen peroxide; In acetonitrile; at 30 ℃; for 1h; Product distribution; reaction in the presence m-CPBA as peroxy acid; oxidation of saturated hydrocarbons with "H2O2-manganese(IV)complex-peroxycarboxylic acid" reagent; selectivity; effect of peroxy acid; effect of reaction conditions, additives;

DOI:10.1007/BF02641538

upstream raw materials:

3-methyl-7-oxabicyclo[4.1.0]heptane

p-methylcyclohexanol

trans-4-methylcyclohexan-1-ol

cis-4-methylcyclohexanol

Downstream raw materials:

4-methyl-cycloheptanone

4,4'-dimethyl-2,2'-methanediyl-bis-cyclohexanone

4-methyl-2,6-bis(4-methylbenzylidene)cyclohexanone

4-methyl-(1,1-dichloro)methylene-cyclohexanone

Refernces

• 1、 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.
• 2、 -. "CATALYTIC PROCESS". Paragraph 0224; 0244; 0248. . Retrieved 2021/12/03.