5-Hexen-2-one

Base Information

• Chemical Name: 5-Hexen-2-one
• CAS No.: 109-49-9
• Molecular Formula: C6H10O
• Molecular Weight: 98.1448
• Hs Code.: 29141990
• European Community (EC) Number: 203-675-1
• NSC Number: 6973
• UNII: XWM6RL9YEI
• DSSTox Substance ID: DTXSID0059372
• Nikkaji Number: J1.503B
• Wikidata: Q24816828
• Metabolomics Workbench ID: 5441
• Mol file: 109-49-9.mol

Synonyms:5-hexene-2-one

Chemical Property of 5-Hexen-2-one

Chemical Property:

• Appearance/Colour: Clear colorless liquid, typical ketone odor
• Vapor Pressure: 10.1mmHg at 25°C
• Melting Point: -71.05°C (estimate)
• Refractive Index: n20/D 1.419(lit.)
• Boiling Point: 129.5 °C at 760 mmHg
• Flash Point: 23.9 °C
• PSA: 17.07000
• Density: 0.819 g/cm³
• LogP: 1.54160
• Storage Temp.: Flammables area
• Water Solubility.: Soluble in water.
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 98.073164938
• Heavy Atom Count: 7
• Complexity: 74.2

Purity/Quality:

≥99.0% ^*data from raw suppliers

5-Hexen-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.
• Hazard Codes: R10:Flammable.
• Statements: 10
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)CCC=C
• Uses: Intermediate in pharmaceutical synthesis, perfumes, fungicides, insecticides, fine chemicals. Allyl Acetone is used as a nature identical flavor and fragrance. And it is also used to produce 2-methyl-hex-5-en-2-ol.

Technology Process of 5-Hexen-2-one

There total 95 articles about 5-Hexen-2-one 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: 97.0%

hex-5-en-2-one oxime (59239-06-4) → 5-Hexen-2-one (109-49-9)

Guidance literature:

hex-5-en-2-one oxime; With 2,2'-dipyridyldiselenide; trimethylphosphane; In tetrahydrofuran; toluene; at 20 ℃; for 0.0333333h;

With water; In tetrahydrofuran; at 20 ℃; for 0.5h; Further stages.;

DOI:10.1016/j.tetlet.2004.06.001

Reference yield: 80.0%

2-acetyl-pent-4-enoic acid ethyl ester (610-89-9,84984-48-5) → 5-Hexen-2-one (109-49-9)

Guidance literature:

With sodium hydroxide; In water; for 2h; Reflux;

DOI:10.1016/j.tet.2014.12.088

Reference yield: 80.0%

dichloromethane (75-09-2) + 1-(4-morpholinyl)-4-penten-1-one (58170-51-7) → 5-Hexen-2-one (109-49-9)

Guidance literature:

dichloromethane; 1-(4-morpholinyl)-4-penten-1-one; With titanium tetrachloride; magnesium; In tetrahydrofuran; at 0 ℃; for 1.05h; Inert atmosphere;

With water; potassium carbonate; chemoselective reaction; Inert atmosphere;

DOI:10.1021/ol8004326

upstream raw materials:

diphenylether

allyl acetoacetate

2,2-bis-allyloxy-propane

hex-5-en-2-ol

Downstream raw materials:

5-(4-isopropyl-phenyl)-hexan-2-one

9,13-dimethyl-tetradeca-111,6,8,12-tetraen-5-one

5-(5-isopropyl-2-methyl-phenyl)-hexan-2-one

1,3-bis-(1,3-dioxo-hept-6-enyl)-benzene

Refernces

• 1、 ?mit, Biljana M.,Pavlovi?, Radoslav Z.. "Three-step synthetic pathway to fused bicyclic hydantoins involving a selenocyclization step". . p. 1101 - 1108. Retrieved 2015.
• 2、 Hooz,Layton. "". . p. 1626. Retrieved 1970.
• 3、 Chen, Shuming,Han, Feng,Houk, K. N.,Ivlev, Sergei,Meggers, Eric,Xie, Xiulan,Ye, Chen-Xi. "Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis". . p. 13552 - 13556. Retrieved 2020.
• 4、 Procopio, Antonio,Dalpozzo, Renato,De Nino, Antonio,Nardi, Monica,Sindona, Giovanni,Tagarelli, Antonio. "Erbium(III) triflate: A valuable catalyst for the rearrangement of epoxides to aldehydes and ketones". . p. 2633 - 2635. Retrieved 2004.
• 5、 Kupin,Petrow. "". . p. 3999,4001;engl.Ausg.S.3958. Retrieved 1959.
• 6、 Shono, Tatsuya,Ohmizu, Hiroshi,Kise, Naoki. "A NOVEL SYNTHESIS OF TERMINAL OLEFINS BY ANODIC OXIDATION OF CARBOXYLIC ACIDS HAVING A TRIMETHYLSILYL GROUP ON THE β-POSITION". . p. 1517 - 1520. Retrieved 1980.
• 7、 Martín, Manuel,Martínez, Gabriel,Urpí, Fèlix,Vilarrasa, Jaume. "Conversion of ketoximes to ketones with trimethylphosphine and 2,2′-dipyridyl diselenide". . p. 5559 - 5561. Retrieved 2004.
• 8、 Khanova,Sultanova,Dokichev,Zlotskii. "Reaction of methyl diazoacetate with unsaturated heterocyclic derivatives of carbonyl compounds catalyzed by Rh2(OAc)4". . p. 106 - 108. Retrieved 2007.
• 9、 Wang, Hai,Wu, Xiao-Feng,Yin, Zhiping,Zhang, Youcan. "Iron-catalyzed carbonylative cyclization of γ,δ-unsaturated aromatic oxime esters to functionalized pyrrolines". supporting information. p. 7045 - 7048. Retrieved 2020/07/14.