2497-21-4

Basic information

• Product Name: 4-HEXEN-3-ONE
• Synonyms: FEMA 3352;4-HEXEN-3-ONE;4-HEXENE-3-ONE;(4E)-4-Hexen-3-one;(E)-CH3CH=CHC(=O)C2H5;2-Hexen-4-one;2-Hexene-4-one;ethyl1-propenylketone
• CAS NO: 2497-21-4
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.14
• EINECS: 219-681-2
• Product Categories: C3 to C6;Carbonyl Compounds;Ketones
• Mol File: 2497-21-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: -71.05°C (estimate)
• Boiling Point: 135-137 °C(lit.)
• Flash Point: 94 °F
• Appearance: Clear colorless to yellow liquid
• Density: 0.858 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.71mmHg at 25°C
• Refractive Index: n20/D 1.44(lit.)
• Storage Temp.: Flammables area
• CAS DataBase Reference: 4-HEXEN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HEXEN-3-ONE(2497-21-4)
• EPA Substance Registry System: 4-HEXEN-3-ONE(2497-21-4)

Safety Data

• Hazard Codes: Xn
• Statements: 10-22-36/37/38
• Safety Statements: 16-26-36/37/39
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 3
• RTECS: MP8659900
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2497-21-4(Hazardous Substances Data)

Usage

Description

4-Hexen-3-one is an unsaturated aldehyde with a pungent, acrid, metallic, and ethereal odor. It is a clear colorless to yellow liquid and is known to occur naturally in strawberry fruit, essential oil of Ruta graveolens, and Holigarna grahamii leaves. Due to its fruity fragrance, it is also used in the perfume industry.

Uses

Used in Flavor Industry:
4-Hexen-3-one is used as a flavor compound for its pungent mustard, pepper, horseradish, rum, roasted onion, and slightly tropical nuances at 10 ppm.
Used in Perfume Industry:
4-Hexen-3-one is used as a fragrance ingredient for its aroma characteristics at 1.0%, which include pungent, horseradish, and mustard notes with an ethyl vinyl ketone ethereal note, and notes reminiscent of vinegar and rum.
Used in Chemical Synthesis:
4-Hexen-3-one can be synthesized by hydration of 4-hexen-2-yne aqueous H2SO4/HgSO4 or by hydrogenation of 2-hexen-5-yn-4-one over PdCaCO3 catalyst in methanol, making it useful in various chemical applications.

Preparation

By hydration of 4-hexen-2-yne aqueous H2SO4-HgSO4; by hydrogenation of 2-hexen-5-yn-4-one over Pd-CaCO3 catalyst in methanol.

InChI:InChI=1/C6H10O/c1-3-5-6(7)4-2/h3,5H,4H2,1-2H3/b5-3+

Upstream product

• 106-95-6 allyl bromide 
• 107-12-0 propiononitrile 
• 24253-30-3 5-hexen-3-one 
• 590-14-7 1-bromo-1-propene 
• 123-62-6 propionic acid anhydride 
• 563-43-9 ethylaluminum dichloride 
• 592-43-8 2-hexene 
• 17202-79-8 1-vinyl-1-cyclobutanol 
• 100-52-7 benzaldehyde 
• 4984-85-4 propioin 
• 592-41-6 1-hexene 
• 4798-58-7 (E)-hex-4-en-3-ol 
• 68318-01-4 4-chloro-hex-2t-ene 
• 924-41-4 1,5-hexadiene-3-ol 

Downstream Products

• 135328-67-5 Trifluoro-methanesulfonate((Z)-1-methyl-3-trimethylsilanyloxy-pent-2-enyl)-triphenyl-arsonium; 
• 135328-65-3 Trifluoro-methanesulfonate((E)-1-methyl-3-trimethylsilanyloxy-pent-2-enyl)-triphenyl-arsonium; 
• 122617-80-5 5-Phenyltellanyl-hexan-3-one 
• 6124-56-7 4,5-epoxyhexan-3-one 
• 4798-58-7 (E)-hex-4-en-3-ol 
• 688-99-3 5-hexen-3-ol 
• 589-38-8 n-hexan-3-one 
• 127006-44-4 (E)-6-Cyclohexyl-6-hydroxy-5-methyl-hex-4-en-3-one 
• 92694-77-4 1-hydroxy-2-ethyl-1-phenyl-3-pentanone 
• 173975-73-0 4-(cyclohexylhydroxymethyl)-3-hexanone 
• 80201-97-4 rac-5-phenyl-3-hexanone 
• 497181-06-3 5-(4-trimethylsilanyl-benzylsulfanyl)-hexan-3-one 
• 497181-07-4 5-(4-trimethylsilanyl-phenylsulfanyl)-hexan-3-one 
• 6147-92-8 5-methyl-3-octanone 

Relevant articles and documents

Chromium-Catalyzed Production of Diols From Olefins

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

Expedient Synthesis of 1,5-Diketones by Rhodium-Catalyzed Hydroacylation Enabled by C-C Bond Cleavage

A rhodium-catalyzed intermolecular hydroacylation reaction of vinyl cyclobutanols with non-chelating aldehydes has been developed. This reaction offers a new and atom-economical approach for the selective preparation of 1,5-diketones in high yields. Experimental data suggest a sequential ring-opening, transfer hydrogenation, and hydroacylation mechanism. We propose that aldehyde decarbonylation is avoided by the formation of a novel rhodium enolate species that also accounts for the compatibility of a broad range of aldehydes and its anti-Markovnikov selectivity.

POSS-derived mesoporous ionic copolymer-polyoxometalate catalysts with a surfactant function for epoxidation reactions

A series of novel polyoxometalate (POM)-based stable polymeric hybrids were successfully synthesized using polyhedral oligomeric vinylsilsesquioxanes (POSS) and ionic liquids (IL) bearing hydrophobic alkyl chains as the building blocks, followed by ion exchange with Keggin-type phosphotungstic acid (PW). The obtained hybrids POSS-ILx-PW were demonstrated to be mesostructured and amphiphilic materials with good thermal stability. Catalytic tests for the H2O2-based epoxidation of cyclooctene have shown that these newly designed catalysts exhibit extraordinary catalytic activities, catalytic rates, and quite stable reusability. The unique amphiphilic property and the mesoporous structure are revealed to be responsible for the catalysts' excellent performance in epoxidation reactions with H2O2.