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
• Article Data: 15

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

Description

(E)-hex-3-ene-2,5-dione, also known as 3-acetyl-2-hexanone, is a chemical compound characterized by its molecular formula C6H10O2. It presents as a colorless, flammable liquid with a strong odor, and is recognized for its versatility in organic chemistry due to its ability to participate in various chemical reactions.

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 this compound 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 
• 498-66-8 norbornene 
• 67711-62-0 1,4-dimethyl-2,3-dioxa-7-thia-bicyclo(2.2.1)hept-5-ene 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 106-42-3 para-xylene 
• 95-63-6 1,2,4-Trimethylbenzene 
• 638-02-8 2,5-DIMETHYLTHIOPHENE 

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 
• 116857-91-1 1,3-diphenyl-4,5-diacetyl-4,5-diethoxycarbonylpyrazole 
• 110-13-4 2,5-hexanedione 
• 207124-18-3 5-ethyl 4-methyl (1S,3R,4S,5R,6R,7S)-6,7-diacetyl-3-[(tert-butyldiphenylsilyl)oxymethyl]-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate 
• 108-31-6 maleic anhydride 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 78-98-8 2-oxopropanal 
• 109565-93-7 1,3,5-trimethyl-2-(4-nitro-phenyl)-4,7-dihydro-isoindole 
• 625-86-5 2,5-dimethylfuran 

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.

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.