820-69-9

Basic information

• Product Name: (E)-hex-3-ene-2,5-dione
• CAS NO: 820-69-9
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.128
• Mol File: 820-69-9.mol

Chemical Properties

• Boiling Point: 213°Cat760mmHg
• Flash Point: 76.4°C
• Density: 0.971g/cm³
• CAS DataBase Reference: (E)-hex-3-ene-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-hex-3-ene-2,5-dione(820-69-9)
• EPA Substance Registry System: (E)-hex-3-ene-2,5-dione(820-69-9)

Safety Data

• Hazardous Substances Data: 820-69-9(Hazardous Substances Data)

Usage

Uses

Used in the Chemical Industry:
(E)-hex-3-ene-2,5-dione is used as a solvent in various industrial processes for its ability to dissolve a wide range of substances, facilitating different chemical reactions and production of other organic compounds.
Used in the Flavor and Fragrance Industry:
(E)-hex-3-ene-2,5-dione serves as a flavoring agent in the food products industry, enhancing the taste and aroma of various consumables. Additionally, it is utilized as a fragrance additive in the perfumery and personal care products sector, contributing to the creation of appealing scents.
Used in Organic Chemistry Research:
Due to its reactivity and capacity to undergo multiple chemical reactions, (E)-hex-3-ene-2,5-dione is a valuable compound in the field of organic chemistry, particularly for research and development purposes.
Caution:
It is crucial to handle (E)-hex-3-ene-2,5-dione with care, as it is a potential irritant and may pose health risks if not managed properly. Safety measures should be taken to minimize exposure and ensure the safe use of (E)-hex-3-ene-2,5-dione in various applications.

Upstream product

• 17559-81-8 (Z)-hex-3-ene-2,5-dione 
• 625-86-5 2,5-dimethylfuran 
• 66310-18-7 4c-(5-methyl-3-phenyl-[1,4,2]dioxazol-5-yl)-but-3-en-2-one 
• 513-88-2 1,1-Dichloroacetone 
• 67711-62-0 1,4-dimethyl-2,3-dioxa-7-thia-bicyclo(2.2.1)hept-5-ene 
• 95-63-6 1,2,4-Trimethylbenzene 
• 638-02-8 2,5-DIMETHYLTHIOPHENE 
• 106-42-3 para-xylene 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 498-66-8 norbornene 

Downstream Products

• 91968-25-1 (+/-)-4r,5t-diacetyl-1-methyl-cyclohexene 
• 93571-05-2 (5R,6S)-5,6-Diacetyl-4-methyl-cyclohex-2-enecarboxylic acid ethyl ester 
• 92865-34-4 (5S,6R)-5,6-Diacetyl-cyclohex-2-enecarboxylic acid 2-oxo-propyl ester 
• 92656-01-4 (5S,6R)-5,6-Diacetyl-4-methyl-cyclohex-2-enecarboxylic acid 2-oxo-propyl ester 
• 104312-10-9 (S)-3-((R)-1-Hydroxy-3-phenyl-propyl)-hexane-2,5-dione 
• 104312-10-9 (S)-3-((S)-1-Hydroxy-3-phenyl-propyl)-hexane-2,5-dione 
• 116857-91-1 1,3-diphenyl-4,5-diacetyl-4,5-diethoxycarbonylpyrazole 
• 116857-85-3 1,3-diphenyl-4,5-diacetylpyrazole 
• 116857-84-2 1,3-diphenyl-4,5-diacetyl-4,5-dihydropyrazole 
• 7189-05-1 1-(1,3-diphenyl-1H-pyrazol-4-yl)ethan-1-one 
• 116857-90-0 1-(4-methylphenyl)-3-phenyl-4-acetylpyrazole 
• 116857-89-7 1-(4-methylphenyl)-3-phenyl-4,5-diacetylpyrazole 
• 116857-88-6 1-(4-chlorophenyl)-3-phenyl-4-acetylpyrazole 
• 116857-86-4 1-(4-chlorophenyl)-3-phenyl-4,5-diacetyl-4,5-dihydropyrazole 

Relevant articles and documents

Stereoselective Synthesis of cis-2-Ene-1,4-diones via Aerobic Oxidation of Substituted Furans Catalyzed by ABNO/HNO3

We report a highly efficient and selective catalytic system, ABNO (9-azabicyclo-[3.3.1]nonane N-oxyl)/HNO3, for the aerobic oxidation of substituted furans to cis-2-ene-1,4-diones under mild reaction conditions using oxygen as the oxidant. The catalyst system is amenable to various substituted (mon-, di-, and tri-) furans and tolerates diverse functional groups, including cyano, nitro, naphthyl, ketone, ester, heterocycle, and even formyl groups. Based on the control and 18O-labeling experiments, the possible mechanism of the oxidation is proposed.

Merging singlet-oxygen induced furan oxidations with organocatalysis: Synthesis of enantiopure cyclopentanones and hydrindanes

A new methodology is described herein which converts simple and readily accesible furan substrates into complex enantio-enriched carbocyclic skeletons through the implementation of a simple one-pot procedure. Singlet oxygen furan photoxygenation affords an enedione which then participates in an organocatalysed double-Michael reaction with an enal to furnish a cyclopentanone structure with up to four new contiguous stereogenic centres. The enantioselectivity and diastereoselectivity of this process are both excellent. If desired, further aldol-annulation steps can be appended to the cascade reaction sequence to afford key enantiopure hydrindane motifs.

Laccase-catalyzed stereoselective oxidative ring opening of 2,5-dialkylfurans into 2-ene-1,4-diones using air as an oxidant

The laccase-catalyzed ring opening of 2,5-dimethylfuran using air as an oxidant stereoselectively yields (Z)- or (E)-3-hexene-2,5-dione depending on the mediator employed: with TEMPO the (Z)-3-hexene-2,5-dione is formed, while a combination of TEMPO and violuric acid gives (E)-3-hexene-2,5-dione. The (Z)-selective ring cleavage was extended to a variety of symmetrical and unsymmetrical 2,5-dialkylfurans. The Royal Society of Chemistry.

Thermal and microwave assisted reactions of 2,5-disubstituted thienosultines with [60]fullerene: Non-Kekulé biradicals and self-sensitized oxygenation of the cycloadduct

Refluxing an o-dichlorobenzene solution of 2,5-disubstituted thienosultines 10a-f with [60]fullerene for 2-24 h gave both 1:1 and 2:1 cycloadducts in 37-79% isolated yields. The reaction was highly accelerated by microwave irradiation giving comparable yields of cycloadducts. Sultines 10a-f underwent cheletropic extrusion of SO2 to form the corresponding non-Kekulé biradical intermediates 11a-f, which were subsequently trapped by [60]fullerene to form corresponding cycloadducts. The activation energy barriers (ΔGc≠) determined for the boat-to-boat inversion of these 4′,5′,6′,7′-tetrahydrobenzo[c]thieno- [5′,6′:1,2][60]fullerene adducts 12a-f were found to be in the range of 13.5-14.8 kcal/mol. Unexpectedly, one of the monoadduct 12a was found to be labile when kept in air under ambient light. Two new products 15 (a sulfine-enone) and 16 (an endione) were isolated from the decomposed 12a and were found to derive from self-sensitized singlet oxygen reaction on the 2,5-dimethylthieno moiety of 12a.

Titanium silicalite 1 (TS-1) catalyzed oxidative transformations of furan derivatives with hydrogen peroxide

The oxidation of furan derivatives with titanium silicalite 1 (TS-1) and hydrogen peroxide is described. Oxidation products are identified and possible reaction pathways are discussed. It is shown that the oxidation of these compounds occurs via epoxidation of one of the furan double bonds. The initially formed epoxides immediately undergo rearrangement, furans yielding unsaturated 1,4-dicarbonyl compounds and furfuryl alcohols yielding 6-hydroxy-2H-pyran-3(6H) -ones. The latter compounds originate from cyclization of intermediate enedione alcohols. The presented method is particularly useful for the oxidation of 2,5-dimethylfuran to 3-hexene-2,5-dione and the conversion of furfuryl alcohol to 6-hydroxy-2H-pyran-3(6H)-one, a versatile synthon in organic synthesis.

Products of the gas-phase reactions of OH radicals with p-xylene and 1,2,3- and 1,2,4-trimethylbenzene: Effect of NO2 concentration

Aromatic hydrocarbons are important constituents of gasoline fuels, vehicle exhaust, and ambient air in urban areas. In the troposphere, aromatic hydrocarbons, e.g., BTEX and trimethylbenzenes, react essentially only with the hydroxyl (OH) radical. Several product studies of the reaction of OH radicals with BTX and trimethylbenzenes have been conducted, but few of these determined product yields under conditions where the reaction of the OH-aromatic adducts with O2 clearly dominates. GC was used to measure products of the gas-phase reactions of the OH radical with p-xylene and 1,2,3- and 1,2,4-trimethylbenzene in the presence of varying NO2 concentrations. Product analyses showed that the ring-cleavage products 2,3-butanedione and 3-hexene-2,5-dione displayed a dependence of their formation yields on the NO2 concentration, with higher yields from the reactions of the OH-aromatic adducts with O2 than from their reactions with NO2. These ring-cleavage products were primary products of the OH-aromatic adduct reactions. Formation yields extrapolated to zero NO2 concentration should be applicable to ambient atmospheric conditions. The formation yields of 3-hexene-2,5-dione from p-xylene and 1,2,4-trimethylbenzene were comparable to those reported for glyoxal from p-xylene and of methylglyoxal from 1,2,4-trimethylbenzene, thus suggesting that these were coproducts.

Reaction of N-fluoropyridinium salts with Wittig reagents: A novel and convenient approach to symmetric trans-olefins

N-Fluoropyridinium salts were found to react with Wittig reagents containing electron-withdrawing groups to give olefins in 47-83% yield. The mechanism of this conversion is believed in involve single-electron transfer from Wittig reagent to N-fluoropyridinium cation.

Generation and Reactions of Novel Copper Carbenoids through a Stoichiometric Reaction of Copper Metal with gem-Dichlorides in Dimethyl Sulfoxide

Copper metal and such gem-dichlorides as α,α-dichloro acid esters, 1a-e, diphenyldichloromethane, 2, benzal chloride, 3, 1,1-dichloro-2-butene, 5, and carbon tetrachloride, 6, were found to produce copper carbenoid intermediates via α,α-elimination of dichlorides along with the formation of CuCl2(DMSO)2.Thus, 1 and 2 gave substituted olefins via a carbenoid coupling reaction.From 5 and 6, reaction products via the oxygen abstraction from DMSO were produced together with dimethyl sulfide; 3 and 4 were found to cause both types of reactions.The carbenoid intermediates formed from 1 did not cause cyclopropanation reaction with cyclohexene in contrast to the conventional carbalkoxy carbenoid generated by a decomposition reaction of ethyl diazoacetate.Also the carbenoid coupling reaction was completely inhibited by the addition of triphenylphosphine, which was contrastive to the formation of phosphonium ylide with a carbenoid from ethyl diazoacetate.

Reactions of Wittig Reagents with Episulfides or Elemental Sulfur

The reactions of Wittig reagents with episulfides gave symmetrical olefins and triphenylphosphine sulfide in moderate yields.The same olefins were obtained by reactions of Wittig reagents with elementar sulfur.These reactions might proceed through thiocarbonyl intermediates, the existence of which was confirmed by Diels-Alder reactions with dienes.