7431-25-6

Usage

Uses

Used in Paint Industry:
3-Hydroxy-3-methyl-2-butanone oxime is used as an anti-skinning agent in alkyd-based paints for preventing the formation of a skin on the paint's surface. This ensures a smooth and even application, enhancing the paint's performance and appearance.
Used in Chemical Production:
In the production of butadiene, a crucial material for synthetic rubber manufacturing, MEKO is utilized as a stabilizer. This role is vital in maintaining the quality and consistency of the final product.
Used in Polymer Production:
3-Hydroxy-3-methyl-2-butanone oxime is employed as an antioxidant in the production of vinyl polymers. Its antioxidant properties help prevent the degradation of polymers, thereby extending their shelf life and improving their overall performance.
Used in Petroleum Industry:
MEKO is used as a corrosion inhibitor in the petroleum industry. By inhibiting corrosion, it helps protect equipment and infrastructure, reducing maintenance costs and extending the service life of assets.
However, it is essential to handle MEKO with care, as it can be harmful if ingested, inhaled, or absorbed through the skin. Proper safety measures should be taken during its use to minimize potential risks.

InChI:InChI=1/C5H11NO2/c1-4(6-8)5(2,3)7/h7-8H,1-3H3/b6-4-

Upstream product

• 917-64-6 methyl magnesium iodide 
• 135636-66-7 butane-2,3-dione mono-oxime 
• 513-35-9 2-methyl-but-2-ene 
• 52533-27-4 3-bromo-3,4,4-trimethyl-3,4-dihydrodiazete 1.2-dioxide 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 80733-29-5 3-Hydroperoxy-3-methyl-butan-2-one oxime 
• 37557-67-8 2-chloro-2-methyl-3-nitrosobutane 
• 2648-71-7 3-bromo-3-methyl-2-butanone 
• 75-85-4 tert-Amyl alcohol 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 38870-64-3 3-hydroxyamino-3-methyl-butan-2-one oxime 
• 115-22-0 3-Hydroxy-3-methyl-2-butanone 
• 563-80-4 3-methyl-butan-2-one 

Downstream Products

• 115-22-0 3-Hydroxy-3-methyl-2-butanone 
• 6291-17-4 3-amino-2-methylbutan-2-ol 

Relevant academic research and scientific papers

Intermolecular Cope-type hydroamination of alkenes and alkynes using hydroxylamines

The development of the Cope-type hydroamination as a method for the metal- and acid-free intermolecular hydroamination of hydroxylamines with alkenes and alkynes is described. Aqueous hydroxylamine reacts efficiently with alkynes in a Markovnikov fashion to give oximes and with strained alkenes to give N-alkylhydroxylamines, while unstrained alkenes are more challenging. N-Alkylhydroxy-lamines also display similar reactivity with strained alkenes and give modest to good yields with vinylarenes. Electron-rich vinylarenes lead to branched products while electron-deficient vinylarenes give linear products. A beneficial additive effect is observed with sodium cyanoborohydride, the extent of which is dependent on the structure of the hydroxylamine. The reaction conditions are found to be compatible with common protecting groups, free OH and NH bonds, as well as bromoarenes. Both experimental and theoretical results suggest the proton transfer step of the N-oxide intermediate is of vital importance in the intermolecular reactions of alkenes. Details are disclosed concerning optimization, reaction scope, limitations, and theoretical analysis by DFT, which includes a detailed molecular orbital description for the concerted hydroamination process and an exhaustive set of calculated potential energy surfaces for the reactions of various alkenes, alkynes, and hydroxylamines.

Thiol-induced nitric oxide release from 3-halogeno-3,4-dihydrodiazete 1,2-dioxides

In this work we studied the mechanism of nitric oxide (NO) release underlying the vasorelaxant and antiaggregant effect of 3,4-dihydrodiazete 1,2-dioxides (DD). Six derivatives were included in the investigations, namely, 3-bromo- and 3-chloro-3,4,4-trimethyl-DD (1a,b), 3-bromo- and 3- chloro-4-methyl-3,4-hexamethylene-DD (2a,b), 3,3,4,4-tetramethyl-DD (3), and 3-methyl-3,4hexamethylene-DD (4), and their reactivity toward thioIs was analyzed. The 3-bromo- and 3-chloro-DD derivatives were found to react with thiols; this reaction can lead to NO formation, DD 2a being the most reactive compound. 2-(Hydroxyamino)-2-methylbutan-3-one oxime (5a) and 2-hydroxy-2- methylbutan-3-one oxime (6) were the main products isolated from the reaction of la with cysteine. Reaction rates of DD with thiols were dependent upon pH and concentration of the reagents. Maximum rates of NO release corresponded to thiol concentrations in the range of 1 mM. Consistent with reaction kinetics data and products isolated, a reaction mechanism was proposed. Addition of 2a to bovine aortic endothelial cells led to strong NO release indicating a reaction with endogenous thiols. In rat mesenterial arteries, the vasorelaxant action of 2a was only slightly influenced by addition of thiol to the incubation medium. For the most reactive DD derivatives, cytotoxic effects were observed at concentrations roughly 2 orders of magnitude higher than those inducing vasorelaxation.