4-Heptanone

Base Information

• Chemical Name: 4-Heptanone
• CAS No.: 123-19-3
• Molecular Formula: C7H14O
• Molecular Weight: 114.188
• Hs Code.: 2914.19
• European Community (EC) Number: 204-608-9
• ICSC Number: 1414
• NSC Number: 8692
• UN Number: 2710
• UNII: 9BN582JQ61
• DSSTox Substance ID: DTXSID6047650
• Nikkaji Number: J43.327F
• Wikipedia: 4-Heptanone
• Wikidata: Q1287920
• Metabolomics Workbench ID: 5503
• Mol file: 123-19-3.mol

Synonyms:4-Oxoheptane;Butyrone;Di-n-Propyl ketone;Dipropyl ketone;GBL;NSC 8692;Propyl ketone;

Chemical Property of 4-Heptanone

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 5.2 mm Hg ( 20 °C)
• Melting Point: -33 °C
• Refractive Index: 1.407
• Boiling Point: 144 °C at 760 mmHg
• Flash Point: 48.9 °C
• PSA: 17.07000
• Density: 0.808 g/cm³
• LogP: 2.15570
• Storage Temp.: Flammables area
• Solubility.: H2O: insoluble
• Water Solubility.: 4.6 g/L (20 ºC)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 114.104465066
• Heavy Atom Count: 8
• Complexity: 58.8
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99.9% ^*data from raw suppliers

4-Heptanone >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-20/22-20-R20-R10-2017/10/20
• Safety Statements: 24/25-S24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: CCCC(=O)CCC
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes and skin. The vapour is irritating to the respiratory tract. Exposure at high levels could cause lowering of consciousness.
• Effects of Long Term Exposure: The substance defats the skin, which may cause dryness or cracking.
• Description: 4-Heptanone is an organic ketone containing seven carbon atoms. It can be found in urine samples of human being. It arises from in vivo beta-oxidation of 2-ethylhexanoic acid (EHA) from plasticisers, which is similar to the formation of 3-heptanone from valproic acid. It is mainly used as the solvents of nitrocellulose, nitrocellulose paint and synthetic resin and as the raw materials of organic synthesis. It can also be used as a internal standard of gas chromatography-mass spectrometry for the analysis of 3-monochloro-1, 2-propane diol which is a potential carcinogen found in soy sauce. It can be synthesized during the reaction of 1-butanol over base catalysts such as MgO. 4-Heptanone has a penetrating odor and burning taste. It is prepared by passing butyric acid over a wood coal at 425°C and then over cerium oxide at 500°C or over thorium oxide; also over manganese oxide at 400 - 425°C.
• Uses: Solvent for nitrocellulose, oils, resins, and polymers and in flavorings Dipropyl ketone (DPK) is used as a solventin oils, resins, nitrocellulose, and polymers;and as a flavoring compound. 4-Heptanone is used as a solvent for nitrocellulose as well as in organic synthesis. It is involved in the preparation of flavorings. It is used as an intermediate in the synthesis of active pharmaceutical ingredients. Further, it is used in paints and coatings.

Technology Process of 4-Heptanone

There total 257 articles about 4-Heptanone 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: 37.0%

trifluoromethanesulfonic acid ethyl ester (425-75-2) + acetone (67-64-1) → 4-heptanone (123-19-3) + 3-ethyl-2-pentanone (6137-03-7) + 3-ethylheptan-4-one (1528-25-2)

Guidance literature:

With n-butyllithium; potassium hydride; In diethyl ether;

DOI:10.1021/jo00080a042

Reference yield: 18.0%

n-heptane (142-82-5) → 4-heptanone (123-19-3) + n-pentyl methyl ketone (110-43-0) + heptan-3-ol (589-82-2) + 2-Heptanol (52390-72-4,543-49-7) + heptan-4-ol (589-55-9) + heptan-3-one (106-35-4)

Guidance literature:

With iodosylbenzene; In chloroform; acetonitrile; at 0.26 ℃; for 1.5h; Reagent/catalyst; regioselective reaction; Darkness;

DOI:10.1039/d0dt01383h

Reference yield: 7.0%

n-heptane (142-82-5) → 4-heptanone (123-19-3) + n-pentyl methyl ketone (110-43-0) + heptan-3-ol (589-82-2) + 2-Heptanol (52390-72-4,543-49-7) + heptan-3-one (106-35-4)

Guidance literature:

With iodosylbenzene; In chloroform; acetonitrile; at 0.26 ℃; for 1.5h; Reagent/catalyst; regioselective reaction; Darkness;

DOI:10.1039/d0dt01383h

upstream raw materials:

butanoic acid anhydride

ethene

heptan-4-ol

hept-3-yne

Downstream raw materials:

4,7-dipropyl-dec-5-yne-4,7-diol

3-phenylheptan-4-one

ethene

2-Pentanone

Refernces

• 1、 Murkute, Ambareesh D.,Jackson, James E.,Miller, Dennis J.. "Supported mesoporous solid base catalysts for condensation of carboxylic acids". . p. 189 - 199. Retrieved 2011.
• 2、 Minachev, Kh. M.,Atal'yan, O. K.. "TRANSFORMATION OF METAMERIC ESTERS ON NEODYMIUM AND ERBIUM OXIDES". . p. 1308 - 1312. Retrieved 1980.
• 3、 Rode, Edward,Davis, Mark E.,Hanson, Brian E.. "Hydroformylation of Propene with Zeolite-supported Rhodium Phosphine Complexes". . p. 1477 - 1478. Retrieved 1985.
• 4、 Rode, Edward,Davis, Mark E.,Hanson, Brian E.. "Rhodium Zeolites as Bifunctional Catalysts for the Synthesis of 2-Methylhexan-3-one and Heptan-4-one from Propylene, Carbon Monoxide, and Hydrogen". . p. 716 - 717. Retrieved 1985.
• 5、 Wang, Shuai,Iglesia, Enrique. "Experimental and theoretical assessment of the mechanism and site requirements for ketonization of carboxylic acids on oxides". . p. 183 - 206. Retrieved 2017.
• 6、 Bel'skii,I.F. et al.. "-". . . Retrieved 1964.
• 7、 Ibne-Rasa et al.. "". . p. 7894. Retrieved 1973.
• 8、 Murata, Kazuhisa,Matsuda, Akio. "SELECTIVE FORMATION OF KETONES FROM PROPENE, CO AND H2O : COBALT BASED CATALYTIC HYDROCARBONYLATION". . p. 11 - 12. Retrieved 1980.
• 9、 Komarewsky,Coley. "-". . p. 701,3269. Retrieved 1941.
• 10、 Nikishin,Sokova,Kapustina. "Oxidation of secondary alkanols with the system cerium ammonium nitrate-lithium bromide into ketones, α-bromo ketones, and α,α -dibromo ketones". . p. 391 - 395. Retrieved 2010.