17292-61-4

Usage

Uses

Used in Rubber Industry:
(2E)-butane-2,3-dione O-acetyloxime is used as a vulcanization accelerator for both natural and synthetic rubber. It enhances the process of vulcanization, which is essential for improving the strength, elasticity, and durability of rubber products.
Used in Food Industry:
(2E)-butane-2,3-dione O-acetyloxime is used as a flavoring agent in food products. Its unique taste and aroma properties make it suitable for enhancing the flavor of various food items.
Used in Cosmetic Industry:
(2E)-butane-2,3-dione O-acetyloxime is used as a fragrance component in perfumes and other cosmetic products. Its pleasant scent makes it a valuable ingredient in creating appealing fragrances for personal care products.
However, it is important to note that (2E)-butane-2,3-dione O-acetyloxime has been found to have potential toxic and irritant effects on the skin, eyes, and respiratory system. It has been linked to respiratory diseases such as bronchiolitis obliterans, also known as "popcorn lung", in workers exposed to high levels of the compound. Therefore, proper handling and safety measures should be taken when working with this chemical compound to minimize the risk of adverse health effects.

Upstream product

• 14941-17-4 Butane-2,3-dione monooximate anion 
• 830-03-5 4-nitrophenol acetate 
• 135636-66-7 butane-2,3-dione mono-oxime 
• 13031-43-1 4-acetyloxyacetophenone 
• 4232-27-3 2,4-dinitrophenyl acetate 
• 1523-06-4 3-nitrophenyl acetate 
• 15119-62-7 1-acetylsulfanyl-4-nitro-benzene 
• 34231-78-2 3-formylphenyl acetate 
• 878-00-2 4-formylphenyl acetate 
• 75-36-5 acetyl chloride 

Downstream Products

• 6628-81-5 2-acetamido-3-butanone 
• 542-10-9 ethylidene diacetate 
• 64505-07-3 N-(3-oxobut-1-en-2-yl)acetamide 
• 622-45-7 cyclohexyl acetate 
• 135636-66-7 butane-2,3-dione mono-oxime 
• 123-86-4 acetic acid butyl ester 
• 93327-76-5 3-acetyl-4-phenyl-2H-chromen-2-one 
• 1374451-45-2 1-(4-methyl-2-(pyridin-2-yl)phenyl)ethan-1-one 
• 1394868-23-5 1-(5-fluoro-2-(pyridin-2-yl)phenyl)ethan-1-one 
• 137103-78-7 1-(2-(pyridin-2-yl)phenyl)ethan-1-one 

Relevant academic research and scientific papers

Dual photoredox/palladium-catalyzed C-H acylation of 2-arylpyridines with oxime esters

An unprecedented dual photoredox/palladium-catalyzed iminyl-radical-mediated C-C bond cleavage and directed ortho C-H acylation of 2-arylpyridines by using oxime esters is described. Oxime esters can serve as efficient acyl sources through formation of the corresponding acyl radicals by photoredox-catalyzed iminyl-radical-mediated C-C bond cleavage. This redox-neutral protocol features excellent regioselectivity, a broad substrate scope, and good functional-group tolerance with respect to both components, giving a broad range of aryl ketones with generally good yields.

Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids

A photoredox-catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2 has been achieved. Notably, a series of four-, five-, or six-membered cyclic ketone oximes worked well to furnish a wide range of ε-, ζ-, and η-cyanocarboxylic acids in good yields. Furthermore, a series of γ-keto acids also could be obtained by employing acyclic ketone oxime esters as the carbonyl radical precursor. It provides convergent access to diverse biologically important cyanocarboxylic and γ-keto acids.

Reactivity studies of carbon, phosphorus and sulfur-based acyl sites with tertiary oximes in gemini surfactants

Kinetic studies of the reactions of tertiary oximes (monoisonitroso acetone; MINA and butane 2,3 dione monooxime; BDMO) with some carboxylate (p-nitrophenyl acetate and p-nitrophenyl benzoate), phosphate (p-nitrophenyl diphenyl phosphate and bis (2,4-dini

Kinetic study of the reactions of p-nitrophenyl acetate and p-nitrophenyl benzoate with oximate nucleophiles

The reactions of p-nitrophenyl acetate (PNPA) and p-nitrophenyl benzoate (PNPB) with α-nucleophile oximates, that is, butane 2,3-dione monoximate, pralidoximate, and other oximates have been studied in the presence of different cationic surfactants. The f

Comparative nucleophilic reactivities in carboxylate, phosphinate, and thiophosphate esters cleavage

Nucleophilic substitution reaction of p-nitrophenyl acetate (PNPA),p-nitrophenyldiphenyl phosphinate, and pesticide parathion with different a-nucleophiles [I] have been studied at 27°C in different pH in the presence of a novel cationic surfactant. [image omitted] The kinetic study was performed spectrophotometrically under pseudo-first order conditions with the α-nucleophile in excess. The pKa of nucleophiles have also been determined by kinetic method. In the presence of surfactant, the rate constant increased with increasing surfactant concentration up to a limiting value. This behavior has been analyzed in quantitative terms on the basis of pseudo-phase model of micellar catalysis. Finally the nucleophilic reactivity of hydroxamate ions has been compared with other α-nucleophiles, like oxime, hydroxybenzotriazole, and 2-iodosobenzoic acid (IBA). The order of cleavage of electrophilic centers, that is, C=O, P=O, and P=S have also been discussed. Copyright

Solvent effect on the α-effect: Ground-state versus transition-state effects; a combined calorimetric and kinetic investigation

In a study of the solvent effect on the α-effect, second-order rate constants (kNu-) have been determined spectrophotometrically for reactions of a series of substituted phenyl acetates with butan-2,3-dione monoximate (Ox-, α-nucleop

Effect of modification of the electrophilic center on the α effect

We report on a nucleophilic study of esters R-C(=X)-Y-Ar in which the electrophilic center has been modified by replacing O by S in the leaving group or carbonyl center: 4-nitrophenyl acetate (1), S-4-nitrophenyl thioacetate (2), 4-nitrophenyl benzoate (3), and O-4-nitrophenyl thionobenzoate (4). The studies include O- and S- nucleophiles as well as α nucleophiles in H2O at 25.0 ± 0.1°C. The sulfur nucleophile (4-chlorothiophenoxide, 4-ClPhS-) exhibits significant enhanced reactivity for the reactions with thiol and thione esters 2 and 4 compared with their oxygen analogues 1 and 3. On the contrary, the common nucleophile OH- is much less reactive towards 2 and 4 compared with 1 and 3. The effect of changing both the electrophilic center and the nucleofugic center on the reactivity of the other oxygen nucleophiles is not so significant: 4-chlorophenoxide (4-ClPhO-) is four to six times more reactive in the reactions with thiol and thione esters 2 and 4 compared with their oxygen analogues 1 and 3. The α effects exhibited by butan-2,3-dione monoximate (Ox-) and HOO- are strongly dependent on the nature of the electrophilic center of the substrates, indicating that the difference in the ground-state solvation energy cannot be fully responsible for the α effect. Our results clearly emphasize the strong dependence of the α effect on the substrate structure, notably, the nature of the electrophilic center. The impact of change in the nucleofuge (1-→2) and the electrophilic center (3-→4) on reactivity indicates that anucleophiles will need to be "purpose built" for decontamination and nucleophilic degradation of specific biocides.

Solvent effect on the α-effect for the reactions of aryl acetates with butane-2,3-dione monoximate and p-chlorophenoxide in MeCN-H2O mixtures

Second-order rate constants have been measured spectrophotometrically for the nucleophilic reactions of three substituted phenyl acetates with butane-2,3-dione monoximate (Ox-) as an α-nucleophile and p-chlorophenoxide (ClPhO-) as co

The origin of the α-effect: Dissection of ground-state and transition- state contributions

The origin of the α-effect has been probed through a combination of calorimetric and kinetic studies involving butane-2,3-dione monoximate as α- nucleophile and p-chlorophenoxide as normal nucleophile in the reaction with p-nitrophenyl acetate in DMSO-Hs

Solvent effect on rate for anionic nucleophilic substitution reaction of 4-nitrophenyl acetate in aqueous acetonitrile

Second order rate constants have been measured for anionic nucleophilic substitution reactions of 4-nitrophenyl acetate in MeCN-H2O mixtures. The results show rate minima near 30-40 mole % MeCN, which are attributed to changes in solvent structure.