3-Octanone

Base Information

• Chemical Name: 3-Octanone
• CAS No.: 106-68-3
• Molecular Formula: C8H16O
• Molecular Weight: 128.214
• Hs Code.: 29141900
• European Community (EC) Number: 203-423-0
• NSC Number: 60161
• UN Number: 2271
• UNII: 79173B4107
• DSSTox Substance ID: DTXSID3041954
• Nikkaji Number: J3.245J
• Wikipedia: 3-Octanone
• Wikidata: Q18349104
• Metabolomics Workbench ID: 5461
• ChEMBL ID: CHEMBL2269087
• Mol file: 106-68-3.mol

Synonyms:3-octanone

Chemical Property of 3-Octanone

Chemical Property:

• Appearance/Colour: Clear colourless to slightly yellow liquid
• Vapor Pressure: 1.5mmHg at 25°C
• Melting Point: -23 °C
• Refractive Index: n20/D 1.415(lit.)
• Boiling Point: 169.9 °C at 760 mmHg
• Flash Point: 46.1 °C
• PSA: 17.07000
• Density: 0.812 g/cm³
• LogP: 2.54580
• Storage Temp.: Flammables area
• Solubility.: 2.60g/l
• Water Solubility.: 0.7 g/L
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 128.120115130
• Heavy Atom Count: 9
• Complexity: 76.6
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

3-Octanone >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R10:; R36:
• Safety Statements: S16:; S26:; S39:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: CCCCCC(=O)CC
• Description: 3-Octanone has a strong, penetrating, fruity odor reminiscent of lavender. It can be prepared by passing a mixture of vapors of caproic acid and acetic acid over ThO2 at 400°C, or by oxidation of d-ethyl n-amyl carbinol with chromates; another synthetic route is reported.
• Uses: 3-Octanone can be produced by oxidation of 3-octanol or by heating propionic acid and caproic acid over thorium oxide. 3-Octanone is used as an ingredient in soaps, perfumes, lotions, and creams. It is also used as a flavoring agent in foods. U.S. production and importation of 3-octanone was estimated to be relatively low (,25,000 lb at a single site) in 2005 as data for 3-octanone were not included in the 2006 U.S. EPA Inventory Update Reporting database. Perfumery, solvent for nitrocellulose and vinyl resins. 3-Octanone was used to study the effect of TiO2 photo catalyst on the rate and the ratio of products generated in photo catalytic oxidation of 3-octanone. It is used as a flavor and fragrance ingredient.

Technology Process of 3-Octanone

There total 143 articles about 3-Octanone 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: 20.0%

octane (111-65-9) → 3-octanone (106-68-3) + octan-4-one (589-63-9) + octan-4-ol (589-62-8) + rac-3-octanol (589-98-0) + rac-octan-2-ol (4128-31-8,113301-48-7,4128-32-9) + hexyl-methyl-ketone (111-13-7)

Guidance literature:

With [PPh₄]₂[Mn^V(N)(CN)₄]; tetrabutylammonium periodite; acetic acid; In 2,2,2-trifluoroethanol; at 23 ℃; Inert atmosphere;

DOI:10.1002/asia.201601027

Reference yield: 6.0%

octane (111-65-9) → 3-octanone (106-68-3) + octan-4-ol (589-62-8) + hexyl-methyl-ketone (111-13-7)

Guidance literature:

With [Fe₄^III(μ-O)₂(μ-acetate)₆(2,2'-bipyridine)₂(H₂O)₂](NO₃^-)(OH^-); dihydrogen peroxide; acetic acid; In water; acetonitrile; at 32 ℃; for 3h; Overall yield = 33 %Spectr.; Catalytic behavior;

DOI:10.1016/j.molstruc.2018.11.062

Reference yield:

trans-2-Octene (13389-42-9) → 2,3-epoxyoctane (3234-26-2) + 3-octanone (106-68-3) + rac-3-octanol (589-98-0)

Guidance literature:

With iodosylbenzene; In dichloromethane; at 20 ℃; for 12h; Reagent/catalyst; Sealed tube; Inert atmosphere;

DOI:10.1080/10610278.2015.1083102

upstream raw materials:

oct-2-yne

3-octanone dimethyl acetal

rac-3-octanol

sodium proprionate

Downstream raw materials:

5-Aethyl-5-hydroxy-decan

oxime of 3-octanone

rac-3-octanol

octane-2,3-dione

Refernces

• 1、 Uma, Ramalinga,Davies, Maxwell,Crévisy, Christophe,Grée, René. "A tandem allylic alcohol isomerization-aldol condensation catalyzed by Rh and Ru complexes". . p. 3069 - 3072. Retrieved 2001.
• 2、 Hambraeus, Gustav,Nyberg, Nils. "Enzymatic hydrogenation of trans-2-nonenal in barley". . p. 8714 - 8721. Retrieved 2005.
• 3、 Epp, Konstantin,Luz, Ignacio,Heinz, Werner R.,Rapeyko, Anastasia,Llabrés i Xamena, Francesc X.,Fischer, Roland A.. "Defect-Engineered Ruthenium MOFs as Versatile Heterogeneous Hydrogenation Catalysts". . p. 1720 - 1725. Retrieved 2020.
• 4、 Bavykina,Mautscke,Makkee,Kapteijn,Gascon,Llabrési Xamena. "Base free transfer hydrogenation using a covalent triazine framework based catalyst". . p. 4166 - 4170. Retrieved 2017.
• 5、 Uma, Ramalinga,Gouault, Nicolas,Crévisy, Christophe,Grée, René. "Development of new iron catalysts for the tandem isomerization-aldol condensation of allylic alcohols". . p. 6187 - 6190. Retrieved 2003.
• 6、 Servin, Paul,Laurent, Régis,Dib, Hanna,Gonsalvi, Luca,Peruzzini, Maurizio,Majoral, Jean-Pierre,Caminade, Anne-Marie. "Number of terminal groups versus generation of the dendrimer, which criteria influence the catalytic properties?". . p. 3876 - 3879. Retrieved 2012.
• 7、 Cele, Mduduzi N.,Friedrich, Holger B.,Bala, Muhammad D.. "Liquid phase oxidation of n-octane to C8 oxygenates over modified Fe-MOF-5 catalysts". . p. 99 - 102. Retrieved 2014.
• 8、 Poreddy, Raju,Engelbrekt, Christian,Riisager, Anders. "Copper oxide as efficient catalyst for oxidative dehydrogenation of alcohols with air". . p. 2467 - 2477. Retrieved 2015.
• 9、 Hwu, Jih Ru. "A Novel Oxidative Desulfonylation. Facile Conversion of Sulfones to Aldehydes or Ketones". . p. 4432 - 4433. Retrieved 1983.
• 10、 Harwardt, Thomas,Francio, Giancarlo,Leitner, Walter. "Continuous-flow homogeneous catalysis using the temperature-controlled solvent properties of supercritical carbon dioxide". . p. 6669 - 6671. Retrieved 2010.