3376-33-8

Usage

Uses

Used in Organic Synthesis:
(1Z)-1-phenylethanone O-methyloxime is utilized as a key intermediate in organic synthesis for the production of various organic compounds. Its ability to undergo multiple chemical reactions makes it a preferred choice for creating a wide array of chemical entities.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, (1Z)-1-phenylethanone O-methyloxime serves as a crucial component in the synthesis of numerous drugs and pharmaceutical intermediates. Its versatility in chemical transformations allows for the development of a broad spectrum of medicinal agents.
Used as a Reagent in Chemical Reactions:
(1Z)-1-phenylethanone O-methyloxime is also employed as a reagent in various chemical processes. Its unique properties facilitate specific reactions that are essential for the advancement of research and development in chemical science.

Upstream product

• 613-91-2 acetophenone oxime 
• 77-78-1 dimethyl sulfate 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 593-56-6 N-methoxylamine hydrochloride 
• 98-86-2 acetophenone 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 31376-92-8 (1E,1Z)-2-bromo-N-methoxy-1-phenylethanimine 
• 32349-36-3 α-Methoxyiminophenylacetaldehyd 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 35301-62-3 N-phenyl-N-acetyl-O-methylhydroxylamine 
• 74515-92-7 3,6-dimethyl-3,6-diphenyl-1,2,4,5-tetraoxacyclohexane 
• 98-86-2 acetophenone 
• 103794-57-6 (R)-O-methyl-N-(α-methylbenzyl)hydroxylamine 
• 142065-70-1 2-diazo-1-phenylethanone O-methyloxime 
• 67-62-9 O-Methylhydroxylamin 
• 135923-85-2 O-Methyl-N-((S)-1-phenyl-ethyl)-hydroxylamine 
• 135879-69-5 (R)-O-methyl-N-(α-methylbenzyl)hydroxylamine 
• 1010840-08-0 (Pd((CH₃CNC₆H₃(C(CH₃)3)2)2)(C₆H₄C(CH₃)NOCH₃))⁽¹⁺⁾ 

Relevant academic research and scientific papers

Access to Branched Allylarenes via Rhodium(III)-Catalyzed C-H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate

A rhodium(III)-catalyzed C-H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.

Direct Oxygenation of C-H Bonds through Photoredox and Palladium Catalysis

This report presents the oxygenation of C-H bonds via the merger of photocatalysis and Pd catalysis. Herein, we describe the utilization of a photocatalyst to oxidize an organopalladium(II) intermediate to high-valent PdIII or PdIV intermediates, which promotes the formation of C-O bonds. The demonstrated method works efficiently with various directing groups, such as oxime ether and benzothiazole. The applicability of this direct C-O bond formation method is shown by synthesizing several metal complexes of 2-(benzo[d]thiazol-2-yl)phenol that can be used in organic light-emitting diodes and pharmaceuticals.

Regio-Divergent C—H Alkynylation with Janus Directing Strategy via Ir(III) Catalysis

Directing strategy has been extensively exploited to maintain activity and selectivity for the rapid access to functionalized molecules and pharmaceutical targets. However, ‘one-to-one’ activation model was usually achieved through traditional directing strategy. Herein, we achieved ‘one-to-two’ activation model by slight modification of simple and practical ketoxime and amide functionality. With judicious choice of directing groups, Csp3—H and Csp2—H bond alkynylation reaction, and more significantly, dehydrogenative Csp3—H alkynylation, were realized, enabling the regio-divergent late-stage modifications of pharmaceuticals.

Nitrate promoted mild and versatile Pd-catalysed C(sp2)-H oxidation with carboxylic acids

A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp2)-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O-aryl esters. Moreover, the superiority of the nitrate additive in this mild transformation was further determined by experimental and computational evidence.

Rhodium(III)-Catalyzed Oxidative Annulation of Ketoximes with Sulfonamide: A Direct Approach to Indazoles

A rhodium(III)-catalyzed intermolecular C-H amination of ketoxime and iodobenzene diacetate-enabled N-N bond formation in the synthesis of indazoles has been developed. A variety of functional groups were well tolerated, providing the corresponding produc

Rhodium(III)-Catalyzed Oxidative Annulation of Ketoximes with Sulfonamide: A Direct Approach to Indazoles

A rhodium(III)-catalyzed intermolecular C-H amination of ketoxime and iodobenzene diacetate-enabled N-N bond formation in the synthesis of indazoles has been developed. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. Moreover, the nitro-substituted ketoximes are well compatible in this reaction, leading to the corresponding products in moderate to good yields.

Reusable Palladium Nanoparticles Catalyzed Oxime Ether Directed Mono Ortho-Hydroxylation under Phosphine Free Neutral Condition

An efficient, reusable and stable binaphthyl stabilized Pd-nanoparticles (Pd-BNP) catalyzed the direct ortho-C?H hydroxylation of acetophenone oxime ethers under neutral and phosphine ligand-free condition has been developed. A readily available, economic, safe and greener oxidant oxone has been used in this direct ortho-hydroxylation. The scope of the reaction has been studied with various acetophenone oxime ethers including electron rich to electron deficient system and the reaction afforded only mono hydroxylated products in a highly regioselective manner. Several control experiment results confirmed that the oxone is the hydroxyl source. The Pd-BNP catalyst has been reused up to five times. The heterogeneous test confirmed that the reaction is catalyzed by the heterogeneous Pd-BNP catalyst. (Figure presented.).

Catalyst-Controlled [3 + 2] and [4 + 2] Annulations of Oximes with Propargyl Alcohols: Divergent Access to Indenamines and Isoquinolines

Rhodium(III)- and iridium(III)-catalyzed C-H activation of oximes and coupling with propargyl alcohols is discussed. Depending on the catalyst, the reaction pathway switched between [3 + 2] and [4 + 2] annulations, thus giving divergent access to indenami

Palladium-Catalyzed C(sp2)-H Acetoxylation via Electrochemical Oxidation

Palladium-catalyzed arene C(sp2)-H acetoxylation has emerged as a powerful tool to construct a carbon-oxygen (C-O) bond. However, the requirement of stoichiometric chemical oxidants for this transformation possesses a significant disadvantage.

Synthesis of 2-fluorocholine aryl carbonyl compounds

The invention provides a method for synthesizing 2-fluoroarylcarbonyl compounds, which comprises the following steps: converting arylcarbonyl compounds into corresponding carbonyl oxime ether compounds, mildly implementing aryl hydrocarbon chain direct fluoridation of high-selectivity oximido substituent group ortho-position in the presence of a palladium catalyst, a fluoridation reagent and additives, and finally, rehydrolyzing oxime ethers under the action of acid to obtain the 2-fluoroarylcarbonyl compounds. The fluoridation method has the advantages of mild reaction conditions, high substrate adaptability, high fluoridation selectivity and the like, is simple to operate, and has higher application research value.