Cyclooctanone

Base Information

• Chemical Name: Cyclooctanone
• CAS No.: 502-49-8
• Molecular Formula: C8H14O
• Molecular Weight: 126.199
• Hs Code.: 29142990
• European Community (EC) Number: 207-940-2
• NSC Number: 9475
• UNII: Z4GO9P8SUZ
• DSSTox Substance ID: DTXSID3060114
• Nikkaji Number: J6.200F
• Wikipedia: Cyclooctanone
• Wikidata: Q20054504
• Pharos Ligand ID: LYHBYV8A75KU
• Metabolomics Workbench ID: 125220
• ChEMBL ID: CHEMBL18737
• Mol file: 502-49-8.mol

Synonyms:NSC 9475;cyclooctan-1-one;

Chemical Property of Cyclooctanone

Chemical Property:

• Appearance/Colour: colorless to white crystalline low melting solid
• Vapor Pressure: 0.47mmHg at 25°C
• Melting Point: 32-41 °C(lit.)
• Refractive Index: 1.447
• Boiling Point: 193.229 °C at 760 mmHg
• Flash Point: 72.778 °C
• PSA: 17.07000
• Density: 0.912 g/cm³
• LogP: 2.29980
• Storage Temp.: Store below +30°C.
• Solubility.: 15g/l
• Water Solubility.: Soluble in water at 20°C 15g/L. Soluble in acetone, alcohol, chloroform, methanol and benzene.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 126.104465066
• Heavy Atom Count: 9
• Complexity: 86.7

Purity/Quality:

98% ^*data from raw suppliers

Cyclooctanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C,Xi
• Statements: 34-52/53-36/37/38
• Safety Statements: 45-36/37/39-26-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCCC(=O)CCC1
• Uses: Cyclooctanone is a aliphatic cycle that exhibited inhibitory activity towards aldosterone synthase, a promising therapeutic target for the treatment of cardiovascular diseases related to abnormally high aldosterone level. Cyclooctanone is a aliphatic cycle that exhibited inhibitory activity towards aldosterone synthase, a promising therapeutic target for the treatment of cardiovascular diseases related to abnormally high aldosterone level. It is also used in the synthesis of 14-membered lactones.

Technology Process of Cyclooctanone

There total 237 articles about Cyclooctanone 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: 96.0%

1,2-cyclooctene (931-88-4,22770-27-0,3958-30-3,25267-51-0) → cycloactanone (502-49-8) + cyclooctanol (696-71-9)

Guidance literature:

With tetrachloromethane; copper(II) choride dihydrate; chromium(III) acetylacetonate; water; at 150 ℃; for 12h; Sealed tube;

DOI:10.1134/S1070428013100047

Reference yield: 81.0%

cis-Cyclooctene (931-88-4,931-87-3,25267-51-0) → cycloactanone (502-49-8) + cis-1,2-epoxycyclooctane (4925-71-7)

Guidance literature:

With oxygen; magnesium oxide supported polytitazane-tin tetrachloride; In 1,4-dioxane; at 80 ℃; for 20h;

DOI:10.1039/CC9960001355

Reference yield: 69.0%

Cyclooctan (292-64-8) → cycloactanone (502-49-8) + cyclooctanol (696-71-9) + cyclooctylhydroperoxide (5130-47-2)

Guidance literature:

With O₄₀PV₂W₁₀^(8-)*5C₁₆H₃₆N⁽¹⁺⁾; dihydrogen peroxide; In acetonitrile; at 80 ℃; for 9h; Inert atmosphere;

DOI:10.2298/JSC111124040T

upstream raw materials:

diazomethane

methanol

diethyl ether

cyclohexanone

Downstream raw materials:

1-cyclooctenyl acetate

cyclononanone

cyclodecanone

2-cyclooct-1-enyl-naphthalene

Refernces

• 1、 Barloy, Laurent,Battioni, Pierrette,Mansuy, Daniel. "Manganese Porphyrins Supported on Montmorillonite as Hydrocarbon Mono-oxygenation Catalysts: Particular Efficacy for Linear Alkane Hydroxylation". . p. 1365 - 1367. Retrieved 1990.
• 2、 Tse, Chun-Wai,Chow, Toby Wai-Shan,Guo, Zhen,Lee, Hung Kay,Huang, Jie-Sheng,Che, Chi-Ming. "Nonheme iron mediated oxidation of light alkanes with oxone: Characterization of reactive oxoiron(IV) ligand cation radical intermediates by spectroscopic studies and DFT calculations". . p. 798 - 803. Retrieved 2014.
• 3、 Jatupisarnpong, Jirarot,Trakarnpruk, Wimonrat. "Transition metal-substituted polyoxometalates supported on MCM-41 as catalysts in the oxidation of cyclohexane and cyclooctane with H2O2". . p. 152 - 153. Retrieved 2012.
• 4、 Company, Anna,Gomez, Laura,Gueell, Mireia,Ribas, Xavi,Luis, Josep M.,Que Jr., Lawrence,Costas, Miquel. "Alkane hydroxylation by a nonheme iron catalyst that challenges the heme paradigm for oxygenase action". . p. 15766 - 15767. Retrieved 2007.
• 5、 Blicke et al.. "-". . p. 5418. Retrieved 1953.
• 6、 Atlay, Mark T.,Preece, Michael,Strukul, Giorgio,James, Brian R.. "Selective Homogeneous Catalytic Oxidation of Olefins using Oxygen/Hydrogen Mixtures: Oxygen Atom Transfer from an Iridium Hydroperoxide". . p. 406 - 407. Retrieved 1982.
• 7、 Maldotti, A.,Bartocci, C.,Amadelli, R.,Polo, E.,Battioni, P.,Mansuy, D.. "Oxidation of Alkanes by Dioxygen Catalysed By Photoactivated Iron Porphyrins". . p. 1487 - 1489. Retrieved 1991.
• 8、 Matsuura,T. et al.. "". . p. 3095 - 3100. Retrieved 1971.
• 9、 Szymańska, Anna,Nitek, Wojciech,Mucha, Dariusz,Karcz, Robert,Pamin, Katarzyna,Po?towicz, Jan,?asocha, Wies?aw. "Structural studies and physico-chemical properties of new oxodiperoxomolybdenum complexes with nicotinic acid". . p. 39 - 46. Retrieved 2013.
• 10、 Punniyamurthy, T.,Kalra, Swinder Jeet Singh,Iqbal, Javed. "Cobalt(II) Catalyzed Biomimetic Oxidation of Hydrocarbons in the Presence of Dioxygen and 2-Methylpropanal". . p. 8497 - 8500. Retrieved 1995.