3848-24-6

Basic information

• Product Name: 2,3-HEXANEDIONE
• Synonyms: FEMA 2558;2,3-HEXANEDIONE;ACETYL BUTYRYL;2,3-Hexanodione;Methyl propyl diketone;methylpropyldiketone;hexane-2,3-dione;2 3-HEXANEDIONE 90+%
• CAS NO: 3848-24-6
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• EINECS: 223-350-8
• Mol File: 3848-24-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: -30 °C
• Boiling Point: 128 °C(lit.)
• Flash Point: 83 °F
• Appearance: Yellow liquid
• Density: 0.934 g/mL at 25 °C(lit.)
• Vapor Density: 3.9 (vs air)
• Vapor Pressure: 10 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.412(lit.)
• Storage Temp.: Flammables area
• Solubility: H2O: soluble (slightly soluble)
• Explosive Limit: 1.2-5.9%(V)
• Water Solubility: Partly miscible in water.
• Stability: Stable. Flammable. Incompatible with strong bases, strong oxidizing agents.
• BRN: 1699896
• CAS DataBase Reference: 2,3-HEXANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-HEXANEDIONE(3848-24-6)
• EPA Substance Registry System: 2,3-HEXANEDIONE(3848-24-6)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36/37/39-16
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 2
• RTECS: MO3140000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 3848-24-6(Hazardous Substances Data)

Usage

Description

2,3-Hexanedione, also known as an alpha-diketone, is a yellow liquid with a powerful, creamy, sweet, and buttery odor. It has a sharp penetrating odor in high concentrations but a sweet, aromatic odor when diluted. It is synthesized from various methods, including propionyl aldehyde condensed over ethyl acetylacetate, methyl butyl ketone and ethyl propyl ketone, and acetoxy mesityl oxide. It is characterized by its buttery, cheese taste and is found in various food items such as fermented soybean, peach, roasted chicken, beer, coffee, shoyu, and clam.

Uses

Used in Food Industry:
2,3-Hexanedione is used as a flavoring agent for its creamy, fruity, toasted brown, and caramellic taste characteristics at 50 ppm. It is commonly found in various food items, contributing to their distinct taste and aroma.
Used in Chemical Research:
2,3-Hexanedione is used as a reactant in the synthesis of macrocyclic tetradentate 12-membered nitrogen donor (N4) ligand when it reacts with ethylenediamine. This application is significant in chemical research and development, particularly in the field of coordination chemistry.
Used in Aroma Compounds Release Studies:
2,3-Hexanedione is utilized to evaluate the influence of xanthan concentration on the release of aroma compounds in xanthan-thickened food model systems. This application aids in understanding the interaction between thickeners and aroma compounds, which is crucial for the development of food products with desired sensory properties.

Preparation

From propionyl aldehyde condensed over ethyl acetylacetate; the resulting product is then oxidized (H2O2 and sodium tungstate), hydrolyzed and finally decarboxylated to 2,3-dexanedione; from methyl butyl ketone and ethyl propyl ketone by way of the monoxime; also from acetoxy mesityl oxide

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

2,3-HEXANEDIONE is incompatible with strong oxidizing agents and strong bases.

Fire Hazard

2,3-HEXANEDIONE is flammable.

InChI:InChI=1/C6H10O2/c1-3-4-6(8)5(2)7/h3-4H2,1-2H3

Upstream product

• 17257-81-7 1-(3-ethyl-oxiranyl)-ethanone 
• 42563-83-7 3-(hydroxyimino)hexan-2-one 
• 626-93-7 n-hexan-2-ol 
• 3031-66-1 3-hexyn-2,5-diol 
• 591-78-6 n-hexan-2-one 
• 589-38-8 n-hexan-3-one 
• 1629-60-3 1-hexene-3-one 
• 123-38-6 propionaldehyde 
• 116-09-6 hydroxy-2-propanone 
• 54123-75-0 3-hydroxy-2-hexanone 
• 17620-90-5 3-(triphenyl-λ⁵-phosphanylidene)-hexan-2-one 
• 108-24-7 acetic anhydride 
• 123-72-8 butyraldehyde 
• 54073-43-7 2-Hydroxy-hexan-3-one 

Downstream Products

• 15986-80-8 2-Propyl-3-methylpyrazine 
• 152519-33-0 (S)-2-hydroxyhexan-⁽³⁾-one 
• 54073-43-7 2-Hydroxy-hexan-3-one 
• 54123-75-0 3-hydroxy-2-hexanone 
• 343613-70-7 (Z)-3-(4-chlorophenyl)-4-methylene-5-propylidene-1,3-oxazolidin-2-one 
• 68487-07-0 1-Hydroxy-1-methyl-1-phenylpentan-2-one 
• 868059-55-6 (Z)-3-(3-chlorophenyl)-4-methylene-5-propylidene-1,3-oxazolidin-2-one 

Relevant articles and documents

KINETICS AND MECHANISM OF OXIDATION OF SOME KETONES BY N-BROMOACETAMIDE

The kinetics of oxidation of n-butyl methyl ketone (n-BMK) and i-butyl methyl ketone (i-BMK) by N-bromoacetamide (NBA) is studied in perchloric acid media in the presence of mercuric acetate.The main product of the oxidation is the corresponding 1,2-dicarbonyl compound.The reaction order with respect to NBA is zero while with respect to ketone and H+ it is unity.Mercuric acetate, acetamide and sodium perchlorate have negligible effect on the reaction rate, while the dielectric effect is negative.A solvent isotope effect (k0(D2O)/k0(H2O) = 1.80-2.05 and 1.70-2.06 for n-BMK and i-BMK, respectively ) at 35 deg C is observed.On the basis of the available evidence a suitable mechanism consistent with the experimental results is proposed in which it is suggested that the mechanistic route for NBA oxidation is through the enol form of the ketone in an acidic medium.

Selective alkene oxidation with H2O2 and a heterogenized Mn catalyst: Epoxidation and a new entry to vicinal cis-diols

Covalent anchoring of 1,4-dimethyl-1,4,7-triazacyclononane on silica gel is the first step in the preparation of a heterogenized Mn catalyst. When H2O2 is used as the oxidant, this material can catalyze the vicinal cis- dihydroxylation of disubstituted olefins, as shown schematically here. Both enantiomers of the product are obtained.

Cobalt(II)-Catalyzed Reaction of Aldehydes with Acetic Anhydride under an Oxygen Atmosphere: Scope and Mechanism

The reaction of aldehydes with acetic anhydride in the presence of catalytic cobalt(II) chloride under an oxygen atmosphere at ambient temperature is dependent upon the reaction medium.Aliphatic aldehydes react in acetonitrile to give 1,2-diones whereas the aromatic aldehydes are acylated to yield the corresponding acylals.On the other hand, carboxylic acids are obtained from aliphatic and aromatic aldehydes by conducting the reaction in dichloroethane or benzene.Cobalt(II) chloride in acetonitrile catalyzes the conversion of aliphatic aldehydes to the correspondinganhydrides in the absence of acetic anhydride whereas aromatic aldehydes remain largely unaffected under these conditions.A preliminary mechanistic study in three different solvents (i.e. acetonitrile, dichloroethane, and DMF) has revealed that in acetonitrile and in the presence of acetic anhydride, aliphatic aldehydes behave differently than aromatic aldehydes.Some trapping experiments using methyl acrylate and stilbene have been conducted to demonstrate the occurence of an acyl cobalt and peroxyacyl cobalt intermediate during these reactions.