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

May be synthesized by hydration of 4-hexen-2-yne aqueous H2S04/HgS04; by hydrogenation of 2-hexen-5-yn-4-one over PdCaC03 catalyst in methanol.

Chemical Properties

Different sources of media describe the Chemical Properties of 2497-21-4 differently. You can refer to the following data:
1. 4-Hexene-3-one has a pungent, acrid, metallic, ethereal odor
2. Clear colorless to yellow liquid

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.

Aroma threshold values

Aroma characteristics at 1.0%: pungent, horseradish and mustard with an ethyl vinyl ketone ethereal note, notes reminiscent of vinegar and rum.

Taste threshold values

Taste characteristics at 10 ppm: pungent mustard, pepper, horseradish, rum, roasted onion and slightly tropical nuances

General Description

4-Hexen-3-one is an unsaturated aldehyde that is reported to occur 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.

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

Upstream product

• 13721-54-5 Vinylethylacetylen 
• 14092-20-7 2-hexen-4-yne 
• 106-95-6 allyl bromide 
• 107-12-0 propiononitrile 
• 4798-58-7 (E)-hex-4-en-3-ol 
• 91001-07-9 (E)-hexa-1,4-dien-3-ol 
• 10575-41-4 hex-4-yn-3-one 
• 563-43-9 ethylaluminum dichloride 
• 625-35-4 trans-chrotonyl chloride 
• 97-93-8 triethylaluminum 
• 4187-86-4 pent-1-yn-3-ol 
• 68318-01-4 4-chloro-hex-2t-ene 
• 33683-44-2 5-hydroxyhexan-3-one 
• 144-62-7 oxalic acid 

Downstream Products

• 589-38-8 n-hexan-3-one 
• 6147-92-8 5-methyl-3-octanone 
• 145123-14-4 4-((E)-1-Ethyl-1-propyl-but-2-enyl)-morpholine 
• 128192-10-9 2,4-dimethyl-3-phenyl-2-cyclopenten-1-one 
• 92694-77-4 syn-4-(phenylhydroxymethyl)-3-hexanone 
• 135266-68-1 syn-4-(phenylhydroxymethyl)-3-hexanone 
• 132455-66-4 syn-4-(phenylhydroxymethyl)-3-hexanone 
• 127006-44-4 (E)-6-Cyclohexyl-6-hydroxy-5-methyl-hex-4-en-3-one 
• 131671-56-2 4-ethylhept-6-en-3-one 
• 377774-20-4 1-cyclohexylidene-butan-2-one 

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.

4-hydroxy-3-hexanone catalytic dehydration method

The invention relates to a 4-hydroxyl-3-hexanone catalytic dehydration method and mainly aims to solve the problems of a catalyst in the prior art, such as low activity, high reaction temperature and low space velocity. According to the technical scheme, 4-hydroxyl-3-hexanone serving as a raw material comes into contact with a catalyst to generate 4-hexylene-3-hexanone under the conditions that the reaction temperature ranges from 200 DEG C to 400 DEG C and the liquid mass space velocity relative to the 4-hydroxyl-3-hexanone is equal to 0.5-15h, wherein the used catalyst has the crystal grain diameter being at most 5mm, and has ZSM-5 zeolite with mesopores and micropores, and the ratio of the volume of the mesopores to the volume of the micropores in the ZSM-5 zeolite is equal to 1.5-10. The problems in the prior art can be well solved by adoption of the technical scheme. The 4-hydroxyl-3-hexanone catalytic dehydration method can be used for industrial production of 4-hexylene-3-hexanone prepared by using the 4-hydroxyl-3-hexanone.