29917-12-2

Usage

Uses

Used in Organic Synthesis:
2,3,4-Pentanetrione, 3-oxime (6CI,7CI,8CI,9CI) is used as a reagent in organic synthesis for its versatile reactivity and potential for forming complex molecules. Its unique structure allows for various chemical reactions, making it a valuable component in the synthesis of a wide range of organic compounds.
Used in Chemical Research:
In the field of chemical research, 2,3,4-Pentanetrione, 3-oxime (6CI,7CI,8CI,9CI) serves as an intermediate in the development of new chemical compounds and processes. Its properties and reactivity are studied to gain insights into the behavior of similar compounds and to explore new applications in various industries.
Used in Pharmaceutical Industry:
2,3,4-Pentanetrione, 3-oxime (6CI,7CI,8CI,9CI) finds applications in the pharmaceutical industry due to its potential for forming complex molecules with therapeutic properties. Its unique structure and reactivity make it a promising candidate for the development of new drugs and pharmaceutical agents.
Used in Agrochemical Industry:
In the agrochemical industry, 2,3,4-Pentanetrione, 3-oxime (6CI,7CI,8CI,9CI) is utilized for its potential applications in the development of agrochemicals, such as pesticides and herbicides. Its versatile reactivity allows for the creation of compounds with specific target effects on pests and weeds, contributing to more efficient and targeted agricultural practices.

InChI:InChI=1/C5H7NO3/c1-3(7)5(6-9)4(2)8/h9H,1-2H3

Upstream product

• 123-54-6 acetylacetone 
• 7664-93-9 sulfuric acid 
• 102826-92-6 4-benzylimino-pentane-2,3-dione-3-oxime 
• 26567-75-9 acetylacetone enol 
• 110-46-3 isopentyl nitrite 

Downstream Products

• 715-99-1 1-phenyl-3,5-dimethyl-4-nitrosopyrazole 
• 1500-92-1 2,4-diacetyl-3,5-dimethyl-1H-pyrrole 
• 67793-08-2 4,6-dimethyl-2-morpholin-4-yl-5-nitroso-isophthalic acid diethyl ester 
• 55464-23-8 2,7-bis-(4-chloro-phenyl)-4,5-dimethyl-2H-imidazo[1,5-b][1,2,5]oxadiazine 
• 67793-01-5 (3,5-Dimethyl-4-nitroso-phenyl)-isopropyl-amine 
• 67793-03-7 3,5-dimethyl-4-nitroso-N,N-diethylaniline 
• 67793-07-1 3,5-Dimethyl-2,6-diaethoxycarbonyl-N,N-diaethyl-p-nitrosoanilin 
• 67793-10-6 (3,5-Dimethyl-4-nitroso-phenyl)-dihexyl-amine 
• 139325-70-5 4-(4-Acetyl-5-methyl-3-oxy-imidazol-1-yl)-benzoic acid 
• 77335-89-8 5-acetyl-2-(4-methoxyphenyl)-4-methylimidazole 
• 588-46-5 N-(phenylmethyl)acetamide 
• 157166-32-0 5-methyl-2-(p-N,N'-dimethylamino-phenyl)-4-acetyloxazole 
• 39825-17-7 3,5-Dimethyl-2-nitroso-phenol 
• 19628-76-3 3,5-dimethyl-4-nitrosophenol 

Relevant academic research and scientific papers

First kinetic discrimination between carbon and oxygen reactivity of enols

(Chemical Equation Presented) Nitrosation of enols shows a well-differentiated behavior depending on whether the reaction proceeds through the carbon (nucleophilic catalysis is observed) or the oxygen atom (general acid-base catalysis is observed). This is due to the different operating mechanisms for C- and O-nitrosation. Nitrosation of acetylacetone (AcAc) shows a simultaneous nucleophilic and acid-base catalysis. This simultaneous catalysis constitutes the first kinetic evidence of two independent reactions on the carbon and oxygen atom of an enol. The following kinetic study allows us to determine the rate constants for both reaction pathways. A similar reactivity of the nucleophilic centers with the nitrosonium ion is observed.

A further study of acetylacetone nitrosation

The nitrosation of acetylacetone (AcAc) has been revised in an aqueous acid medium of perchloric acid and buffers of mono-, di-, or tri-chloroacetic acid. The results show that in the presence of buffers, under conditions of [nit] ? [AcAc] (nit = sodium nitrite) the reaction cannot be studied by UV-Vis spectroscopy, contrary to the recently published paper by Garcia-Rio et al. (J. Org. Chem., 2008, 73, 8198). The present study also corroborates the previously published mechanism of AcAc nitrosation, where no base-catalysis was observed. Contrarily, the low effect of buffers was attributed to the formation of nitrosyl chloro-, dichloro- or trichloro-acetate salts that are new nitrosating agents.

Synthesis and spectroscopic studies of trans-bis-(3,5-dimethyl-4-nitrosopyrazole) dimer

Bis-(3,5-dimethyl-4-nitrosopyrazole) dimer was prepared by reaction of acetyl acetone with nitrous acid and condensation with hydrazine. Spectroscopic techniques, including IR, UV, 1H NMR, and 13C NMR, and CHN analysis were used to identify the product.

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.

A 2D Zinc Coordination Polymer Built from the Mono-deprotonated 4,4′-Azobis(3,5-dimethyl-1H-pyrazole) Ligand

4,4′-Azobis(3,5-dimethyl-1H-pyrazole) (H2azbpz) in its mono-deprotonated form as a pyrazole-pyrazolate ligand was assembled together with zinc(II) into the two-dimensional coordination polymer [Zn(Hazbpz)NO3]·1.25DMF with sql-a topology, constituted by the dinuclear {Zn2(μ-pz)2(Hpz)2}2+ secondary building unit. The μ3- bridging mode of the ligand is in analogy to bridging modes observed for 4-(4-pyridyl)pyrazolates ligands. After the removal of the DMF solvent molecules, ethanol can be adsorbed up to a maximum uptake of 276 mg·g–1 at p/p0 = 0.9 in an S-shaped adsorption isotherm, corresponding to two ethanol molecules per [Zn(Hazbpz)NO3] formula unit. The desorption isotherm reveals that only one EtOH is desorbed until p/p0 = 0.4 and the other one remains hydrogen-bonded in the framework until very low pressures.

Reaction of 1,3-Dicarbonyl Compounds with Nitryl Chloride

Reaction of 1,3-dicarbonyl compounds with nitryl chloride through substitution on the activated methylene group, resulted in the formation of chloro, dichloro and oximino derivatives. - Keywords: 3-Oxobutanoic acid ethyl ester; 2,4-Petanedione; reaction with nitryl chloride

NSC 18725, a Pyrazole Derivative Inhibits Growth of Intracellular Mycobacterium tuberculosis by Induction of Autophagy

The increasing incident rates of drug-resistant tuberculosis (DR-TB) is a global health concern and has been further complicated by the emergence of extensive and total drug-resistant strains. Identification of new chemical entities which are compatible with first-line TB drugs, possess activity against DR-, and metabolically less active bacteria is required to tackle this epidemic. Here, we have performed phenotypic screening of a small molecule library against Mycobacterium bovis BCG and identified 24 scaffolds that exhibited MIC99 values of at least 2.5 μM. The most potent small molecule identified in our study was a nitroso containing pyrazole derivative, NSC 18725. We observed a significant reduction in viable bacilli load of starved Mycobacterium tuberculosis upon exposure to NSC 18725. The action of NSC 18725 was “synergistic” with isoniazid (INH) and “additive” with other drugs in our checkerboard assays. Structure-activity relationship (SAR) studies of the parent compound revealed that pyrazole derivatives without a functional group at fourth position lacked anti-mycobacterial activity in vitro. The derivative with para-chlorophenyl substitution at the first position of the pyrazole ring was the most active scaffold. We also demonstrate that NSC 18725 is able to induce autophagy in differentiated THP-1 macrophages. The induction of autophagy by NSC 18725 is the major mechanism for the killing of intracellular slow and fast-growing mycobacteria. Taken together, these observations support the identification of NSC 18725 as an antimycobacterial compound, which synergizes with INH, is active against non-replicative mycobacteria and induces autophagy in macrophages.

Octanitropyrazolopyrazole: A gem-trinitromethyl based green high-density energetic oxidizer

Environmental concerns demand the replacement of ammonium perchlorate (AP) by a green oxidizer in composite propellants. Herein, we report the synthesis and characterization of a novel green high-density energetic oxidizer octanitropyrazolopyrazole (ONPP). With its high specific impulse (256 s), high density (1.997 g cm-3) and good thermal stability (160 °C), ONPP can potentially replace AP. This journal is

Pyrazolyl-Imidazolium Ligands, Metal Organic Frameworks Comprising the Same and Method of Preparing the Same

According to the present invention, a metal organic framework comprising a pyrazolyl-imidazolium ligand can be produced by synthesizing a ligand including an imidazolium group as a center and a pyrazole group bonded to either or both of the centers, and using the ligand to produce the metal organic framework comprising a pyrazolyl-imidazolium ligand. The pyrazolyl-imidazolium ligand is chemically or thermally stable and is useful for fuel cell or gas separation.COPYRIGHT KIPO 2018

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.