4437-51-8

Basic information

• Product Name: 3,4-Hexanedione
• Synonyms: 3,4-HEXANEDIONE;3,4-DIOXOHEXANE;DIPROPIONYL;DIETHYL-ALPHA, BETA-DI-KETONE;FEMA 3168;Bipropionyl;hexane-3,4-dione;3 4-HEXANEDIONE 90+%
• CAS NO: 4437-51-8
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• EINECS: 224-651-7
• Product Categories: Industrial/Fine Chemicals;Organics;ketone Flavor;C3 to C6;Carbonyl Compounds;Ketones;Alphabetical Listings;Flavors and Fragrances;G-H;Building Blocks;C3 to C6;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 4437-51-8.mol

Chemical Properties

• Melting Point: -10 °C
• Boiling Point: 131 °C(lit.)
• Flash Point: 88 °F
• Appearance: Clear yellow/Liquid
• Density: 0.939 g/mL at 25 °C(lit.)
• Vapor Pressure: 9.91mmHg at 25°C
• Refractive Index: n20/D 1.41(lit.)
• Storage Temp.: Freezer
• Water Solubility: 127 g/L (20 ºC)
• BRN: 1700837
• CAS DataBase Reference: 3,4-Hexanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Hexanedione(4437-51-8)
• EPA Substance Registry System: 3,4-Hexanedione(4437-51-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-36/38-20
• Safety Statements: 23-24/25-37/39-26-16
• RIDADR: UN 1224 3/PG 3
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 4437-51-8(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
3,4-Hexanedione is used as a flavoring agent for imparting a buttery taste and aroma to various food products. It is also used as a fragrance ingredient in the production of perfumes and other scented products.
Used in Chemical Synthesis:
3,4-Hexanedione serves as an important intermediate in the synthesis of various chemicals, including pharmaceuticals, agrochemicals, and specialty chemicals. Its unique chemical structure allows it to be used in a wide range of organic reactions, making it a valuable building block in the chemical industry.

Preparation

By condensation of ethyl propionate in the presence of sodium metal, followed by oxidation of the resulting propionin with copper acetate or ferric chloride.

Biochem/physiol Actions

Odor at 1.0%

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

Upstream product

• 19700-96-0 hexa-1,5-diene-3,4-diol 
• 4984-85-4 propioin 
• 142-71-2 copper diacetate 
• 64-19-7 acetic acid 
• 105-37-3 Ethyl propionate 
• 123-38-6 propionaldehyde 
• 87161-06-6 trans-2-Chlor-2,3-diethyl-3-fluoroxiran 
• 87161-09-9 trans-2,3-Diethyl-2-fluor-3-iodoxiran 
• 87161-07-7 trans-2-Brom-2,3-diethyl-3-fluoroxiran 
• 87161-10-2 trans-2-Brom-3-chlor-2,3-diethyloxiran 
• 922-17-8 hexane-3,4-diol 
• 928-49-4 hex-3-yne 
• 7664-41-7 ammonia 
• 7446-08-4 selenium(IV) oxide 

Downstream Products

• 39081-91-9 2,5-dibromo-3,4-hexanedione 
• 802294-64-0 propionic acid 
• 858212-73-4 propionic acid-(1-ethyl-2-oxo-butylidenehydrazide) 
• 94069-69-9 hexane-3,4-dione-bis-(4-nitro-phenylhydrazone) 
• 589-38-8 n-hexan-3-one 
• 648-36-2 3,3,4,4-Tetrafluor-hexan 
• 83225-58-5 (Z)-3,4,4-Trifluoro-hex-2-ene 
• 172751-05-2 6,7-diethyl-1-methylpteridine-2,4-dione 

Relevant articles and documents

Study on the synthesis of 1,2-diketones

A novel method is discussed for preparation of 1,2-diketones: Esters 1 was used as starting material, the intermediate enol 2 was obtained from sodium and trimethylsilyl chloride via acyloin condensation reaction, while bromine water was used in the further experiment as the oxidation reagent to oxidize compound 2 in the mixed solvent THF/H2O. Four kinds of 1,2-diketones have been synthesized in the new way, one is straight chain compound 3a, 3b and the other is ring compound 3c, 3d. The target compounds were confirmed by IR and 1HNMR. Copyright Taylor & Francis Group, LLC.

Sol-gel synthesis of ceria-zirconia-based high-entropy oxides as high-promotion catalysts for the synthesis of 1,2-diketones from aldehyde

Efficient Lewis-acid-catalyzed direct conversion of aldehydes to 1,2-diketones in the liquid phase was enabled by using newly designed and developed ceria–zirconia-based high-entropy oxides (HEOs) as the actual catalysts. The synergistic effect of various cations incorporated in the same oxide structure (framework) was partially responsible for the efficiency of multicationic materials compared to the corresponding single-cation oxide forms. Furthermore, a clear, linear relationship between the Lewis acidity and the catalytic activity of the HEOs was observed. Due to the developed strategy, exclusively diketone-selective, recyclable, versatile heterogeneous catalytic transformation of aldehydes can be realized under mild reaction conditions.

Synthesis Method of 3,4-hexanedione

A synthesis method of 3,4-hexanedione comprises a step of 4-hydroxy-3-hexanonen oxidation, and in the step of 4-hydroxy-3-hexanonen oxidation, water is used as a catalyst, acetic acid is used as a cocatalyst, and ozone is used as an oxidizing agent to carry out an oxidation reaction on 4-hydroxy-3-hexanonen, and after the reaction, distillation under reduced pressure is carried out to obtain the 3,4-hexanedione. According to the synthesis method of 3,4-hexanedione in the invention, in the process of 4-hydroxy-3-hexanone oxidation, the 4-hydroxy-3-hexanone is placed in the water, the ozone is used for oxidation on the 4-hydroxy-3-hexanone, and the acetic acid is used as the cocatalyst, so that the entire oxidation reaction process is mild in conditions and simple to operate, no sewage is produced when the final product (3,4-hexanedione) is obtained, and the yield is greatly increased.

Silver-Catalyzed Decarboxylative Couplings of Acids and Anhydrides: An Entry to 1,2-Diketones and Aryl-Substituted Ethanes

Silver-catalyzed oxidative decarboxylative couplings of carboxylic acids and anhydrides to produce 1,2-diketones and substituted ethanes were developed. This reaction allows the generation of acyl or alkyl radicals by decarboxylation of the corresponding α-keto acids, alkyl acids and anhydrides, which are sequentially coupled to efficiently construct a new C?C bond. This reaction represents a carboxylic acid decarboxylative alternative that employs a radical termination strategy. (Figure presented.).

Heterogenization of ketone catalyst for epoxidatio by low pressure plasma fluorination of silica gel supports

Low pressure plasma was used for preparing heterogeneous organocatalysts 2-(A)-(C) suitable for dioxirane-mediated epoxidations. Heterogenization was accomplished by adsorption of the methyl perfluoroheptyl ketone (2) on fluorinated supports (A)-(C) deriving from the treatment of commercial C8-silica gel in low pressure plasma fed with fluorocarbons. Catalyst 2-(C) proved to be the most efficient one, promoting epoxidation of an array of alkenes, including unsaturated fatty esters like methyl oleate (10) and the triglyceride soybean oil (11), with the cheap potassium peroxymonosulfate KHSO5 (caroate) as a green oxidant. Notably, the perfluorinated matrix gives rise to the activation of caroate, generating singlet oxygen. Materials were characterized by infrared Attenuated Total Reflectance spectroscopy (ATR-FTIR), X-ray Photoelectron Spectroscopy (XPS) and Emission Scanning Electron Microscope (FESEM).

Insertion of an Isolable Dialkylstannylene into C-Cl Bonds of Acyl Chlorides Giving Acyl(chloro)stannanes

The reactions of isolable dialkylstannylene 1 with 1-adamantanoyl, 2,2-dimethylpropanoyl, benzoyl, and substituted benzoyl chlorides afford the corresponding acyl(chloro)stannanes in good yields. Similar reactions with more reactive acetyl and propanoyl c

Preparation method of 1,2-diketone derivative

The invention discloses a preparation method of a 1,2-diketone derivative. The method comprises the step of enabling a raw material 1,3-diketone derivative to react with a cheap and easily obtained industrial product 2,2,6,6-tetramethyl-1-piperidinyloxy under the catalysis of copper so as to obtain the product 1,2-diketone derivative. According to the preparation method, the 1,3-diketone derivative is used as an initiator, and the raw material is easy to obtain and wide in variety; by utilizing the preparation method, the obtained product types are varied, can be directly used, and can be used for other further reactions; in addition, the reagent dosage in the reaction is less, the pollution is reduced, and the production cost is lowered; moreover the reaction conditions are mild, the reaction operation and the after-treatment process are simple, the reaction time is short, the yield is high, and the preparation method is suitable for industrial production.

Synthesis of ferrocene derivatives with planar chirality via palladium-catalyzed enantioselective C-H bond activation

The first catalytic and enantioselective C-H direct acylation of ferrocene derivatives has been developed. A series of 2-acyl-1-dimethylaminomethylferrocenes with planar chirality were provided under highly efficient and concise one-pot conditions with up to 85% yield and 98% ee. The products obtained could be easily converted to various chiral ligands via diverse transformations.

Oxone-mediated oxidative cleavage of β-keto esters and 1,3-diketones to α-keto esters and 1,2-diketones in aqueous medium

A versatile and highly efficient method for the direct synthesis of α-keto esters and 1,2-diketones has been developed. This approach utilizes the oxidative cleavage of a variety of β-keto esters and 1,3-diketones mediated by an Oxone/aluminum trichloride system. The simple one-step oxidation reaction proceeded selectively in aqueous media to afford products in high yields, short reaction times, and environmentally benign conditions.

Direct carbo-acylation reactions of 2-arylpyridines with α-diketones via Pd-catalyzed C-H activation and selective C(sp2)-C(sp2) cleavage

An efficient carbo-acylation reaction of 2-arylpyridines with α-diketones via Pd-catalyzed C-H bond activation and C-C bond cleavage in the presence of TBHP was developed that generated aryl ketones in good yields. The highly selective formation of aryl ketones was observed when 2-arylpyridines reacted with aromatic/aliphatic α-diketones.