6797-44-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
1-PHENYL-1,2,3-BUTANETRIONE 2-OXIME is used as a key intermediate in the synthesis of pharmaceuticals and agrochemicals for its ability to contribute to the development of new and effective compounds in these industries.
Used in Dye and Perfume Production:
Benzoin oxime is used as a raw material in the production of dyes and perfumes, where its chemical properties contribute to the creation of vibrant colors and distinct fragrances.
Used in Rubber Product Formulation:
1-PHENYL-1,2,3-BUTANETRIONE 2-OXIME is used as an antioxidant in the formulation of rubber products to prevent degradation, thereby improving the lifespan and performance of these products.
Used in Research and Development:
Benzoin oxime is utilized in the research and development of new chemical processes, where its unique properties and reactivity are explored for potential applications in various fields.

InChI:InChI=1/C10H9NO3/c1-7(12)9(11-14)10(13)8-5-3-2-4-6-8/h2-6,14H,1H3/b11-9+

Upstream product

• 109-95-5 ethyl nitrite 
• 93-91-4 1-phenylbutan-1,3-dione 
• 62961-61-9 (Z)-4-hydroxy-4-phenyl-3-buten-2-one 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 7782-77-6 cis-nitrous acid 
• 64-19-7 acetic acid 

Downstream Products

• 110332-83-7 1,3-dihydroxy-1,1,3-triphenyl-butan-2-one oxime 
• 500028-02-4 1-phenylbutane-1,2,3-trione 2,3-dioxime 
• 139520-60-8 2.3-bis-seqtrans-hydroxyimino-1-phenyl-butanone-⁽¹⁾ 
• 2009-96-3 2-diazo-1-phenylbutane-1,3-dione 
• 27318-25-8 3⁽⁵⁾-methyl-5⁽³⁾-phenyl-4-nitrosopyrazole 
• 63833-46-5 ethyl 5-benzoyl-2,4-dimethylpyrrole-3-carboxylate 
• 7171-64-4 1,5-diphenyl-3-methyl-4-nitrosopyrazole 
• 6796-58-3 phenyl-(2-p-tolyl-thiazol-4-yl)-ethanedione 2-oxime 
• 6796-67-4 [2-(4-methoxy-phenyl)-thiazol-4-yl]-phenyl-ethanedione 1-oxime 
• 6796-64-1 [2-(4-chloro-phenyl)-thiazol-4-yl]-phenyl-ethanedione 1-oxime 
• 124292-70-2 1,5-dimethyl-4-nitroso-3-phenyl-1H-pyrazole 
• 6028-99-5 3-phenyl-butane-1,2,3-trione-3-(methyl-phenyl-hydrazone)-2-oxime 
• 474384-64-0 1-amino-4-methyl-5-nitroso-2-oxo-6-phenyl-1,2-dihydro-pyridine-3-carbonitrile 

Relevant academic research and scientific papers

A phosphine-mediated synthesis of 2,3,4,5-tetra-substituted N-hydroxypyrroles from α-oximino ketones and dialkyl acetylenedicarboxylates under ionic liquid green-media

Background: The development of multicomponent reactions (MCRs) in the presence of task-specific ionic liquids (ILs), used not only as environmentally benign reaction media, but also as catalysts, is a new approach that meet with the requirements of sustainable chemistry. In recent years, the use of ionic liquids as a green media for organic synthesis has become a chief study area. This is due to their unique properties such as non-volatility, non-flammability, chemical and thermal stability, immiscibility with both organic compounds and water and recyclability. Ionic liquids are used as environmentally friendly solvents instead of hazardous organic solvents. Objective: We report the condensation reaction between α-oximinoketone and dialkyl acetylene dicarboxylate in the presence of triphenylphosphine to afford substituted pyrroles under ionic liquid conditions in good yields. Result: Densely functionalized pyrroles was easily prepared from reaction of α-oximinoketones, dialkyl acetylene dicarboxylate in the presence of triphenylphosphine in a quantitative yield under ionic liquid conditions at room temperature. Conclusion: In conclusion, ionic liquids are indicated as a useful and novel reaction medium for the selective synthesis of functionalized pyrroles. This reaction medium can replace the use of hazardous organic solvents. Easy work-up, synthesis of polyfunctional compounds, decreased reaction time, having easily available-recyclable ionic liquids, and good to high yields are advantages of present method.

Fosmidomycin analogues with N-hydroxyimidazole and N-hydroxyimidazolone as a chelating unit

Fosmidomycin has been reported to have many biological activities as an antibacterial and antimalarial, along with being a herbicidal agent. Its unique mode of action involves the inhibition of a key step of the non mevalonate pathway by blockade of a crucial enzyme, the 1-deoxy-d-xylulose 5-phosphate reductoisomerase (DXR), whose expression is present in bacteria, plasmodium parasites and higher plants, but not in mammals. Herein we report the development of fosmidomycin and of FR-900098 constrained analogues belonging to an unusual heterocyclic based complexing subunit involving N-hydroxyimidazoles and cyclic N-hydroxyureas.

Nitrite ionic liquids (IL-ONO and [bmim]NO2) as effective nitrosonium sources for the synthesis of α-oximinoketones under mild heterogeneous conditions

Ketones and β-diketones were nitrosated and converted to their corresponding α-oximinoketones using task-specific ionic liquids, 1-(4-nitritobutyl)-3-methylimidazolium chloride, IL-ONO, and 1-butyl-3-methylimidazolium nitrite at room temperature. The results from two ionic liquids are comparable and showed that these IL's are effective nitrosonium sources for the preparation of oximinoketones. The protocol is rapid, the yields are excellent, and the method is simple. Copyright

Silica sulfuric acid/NaNO2 as a novel heterogeneous system for the chemoselective α-nitrosation of β-diketones under mild conditions

A combination of silica sulfuric acid and sodium nitrite in the presence of wet SiO2 was used as an effective nitrosating agent for the nitrosation of β-diketones to their corresponding α-nitroso or α-oximinoketones under mild and heterogenous conditions in moderate to excellent yields.

An efficient and chemoselective method for oximination of β-diketones under mild and heterogeneous conditions

A combination of oxalic acid dihydrate and sodium nitrite in the presence of wet SiO2 was used as an effective nitrosating agent for the nitrosation of β-diketones to their corresponding α-oximinoketones in moderate to excellent yields under mild and heterogenous conditions.

Effects of β-Cyclodextrin on the Keto-Enol Equilibrium of Benzoylacetone and on Enol Reactivity

Both β-cyclodextrin and sodium dodecyl sulfate micelles shift the benzoylacetone keto-enol equilibrium to the enol tautomer by preferentially binding the enol form. The UV-vis spectroscopic method was used to quantify the temperature and solvent effects on the keto-enol equilibrium of benzoylacetone in aqueous acid medium. The comparison between the thermodynamic parameters resulting from the binding of the benzoylacetone enol to sodium dodecyl sulfate micelles and from the inclusion of both keto and enol tautomers into the β-cyclodextrin cavity allows us to draw a picture of the possible complex formed in each case. 1H NMR results suggest that benzoylacetone-enol protrudes deeper inside the β-cyclodextrin cavity, whereas the keto tautomer could only have the phenyl ring enclosed in the β-cyclodextrin cavity interior. Nitrosation in acid medium of benzoylacetone in the presence of β-cyclodextrin is reduced below that of free benzoylacetone, indicating that the cyclodextrin complex protects the benzoylacetone enol tautomer, which is in perfect accordance with our picture of the enol·β-cyclodextrin complex.

Determination of keto-enol equilibrium constants and the kinetic study of the nitrosation reaction of β-dicarbonyl compounds

The keno-enol equilibrium constants of acetylacetone, ethyl acetoacetate and ethyl benzoylacetate in water at 25°C are determined by studying the influence of surfactants on their UV-VIS spectra, following the method applied to benzoylacetone published recently. These measured equilibrium constants are used to obtain the reactivity of the ketones towards several nitrosating agents. For this end, the nitrosation reaction of benzoylacetone, acetylacetone, ethyl acetoacetate and ethyl benzoylacetate are studied in aqueous acidic solution in the presence and absence of Cl-, Br- or SCN-. Analysis of the kinetic data indicates that the rate-limiting step is, in every case, the reaction of the enol.

Studies in nitrosopyrazoles. Part 1. Preparative and spectroscopic studies of some 3,5-dialkyl-4-nitrosopyrazoles

The preparations of a number of 3,5-disubstituted- and 1,3,5-trisubstituted-4-nitrosopyrazoles are described and a range of physical properties of these compounds are measured. Comparison is made with some 2,6-disubstituted nitrosobenzenes and it is shown from 13C NMR spectroscopy that the effects of substitution by flanking tert-butyl groups are moderated in the case of the pyrazoles from those in the aromatic C6 ring due to a lessening of steric hindrance. It is also suggested that steric effects are evident in the preparation of 1,3,5-substituted-4-nitrosopyrazoles when one of the flanking groups to the NO is tert-butyl or phenyl, there being no such effect for the corresponding case of the isobutyl group.