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Usage

Uses

Used in Pharmaceutical Industry:
1-(2-chlorophenyl)-N-hydroxyethanimine is used as an organic intermediate for the synthesis of various pharmaceutical drugs. Its unique structure allows it to be a key component in the development of new medications, contributing to the advancement of healthcare and treatment options.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(2-chlorophenyl)-N-hydroxyethanimine serves as an essential intermediate in the production of agrochemicals. Its role in this industry is vital for the development of effective solutions to protect crops and enhance agricultural productivity.
Used in Dye and Pigment Production:
1-(2-chlorophenyl)-N-hydroxyethanimine is used as a key component in the manufacturing of dyes and pigments. Its chemical properties make it suitable for creating a wide range of colors and shades, which are utilized in various industries such as textiles, plastics, and printing.
Used in Organic Chemical Synthesis:
1-(2-chlorophenyl)-N-hydroxyethanimine is also employed in the synthesis of other organic chemicals. Its versatility and reactivity make it a valuable building block for creating a diverse array of chemical products, further expanding its applications across different industries.

Upstream product

• 609-65-4 o-chlorobenzoyl chloride 
• 89-98-5 2-chloro-benzaldehyde 
• 2039-87-4 2-chlorostyrene 
• 2142-68-9 1-(2-chlorophenyl)ethanone 

Downstream Products

• 71226-16-9 1-(2-Chloro-phenyl)-ethanone O-oxiranylmethyl-oxime 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 533-17-5 N-(2-chlorophenyl)acetamide 
• 896905-07-0 1-(2-chlorophenyl)ethanone O-acetyl oxime 

Relevant academic research and scientific papers

Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of: O -pivaloyl oximes with α-diazo compounds

Chiral RhIII catalysts can catalyze the asymmetric [4+1] spiroannulation of O-pivaloyl oximes with α-diazo homophthalimides under redox-neutral and acid/base-neutral conditions, leading to formation of chiral spirocyclic imines as a result of C-H activation and N-O cleavage. The reaction proceeded with high efficiency and features broad substrate scope, mild reaction conditions, and high to excellent enantioselectivities. This journal is

Access to pyrrolo[2,1-: A] isoindolediones from oxime acetates and ninhydrin via Cu(i)-mediated domino annulations

A copper-mediated domino condensation reaction of readily accessible oxime acetates with ninhydrin is reported to afford pyrrolo[2,1-a]isoindolediones via new C-C & C-N bond formations. A wide range of oxime acetates were shown to generally participate in the reaction to produce the condensed products in excellent yields. The necessary control experiments were performed and the mechanism is proposed to involve sequentially the formation of iminium radical via Cu-mediated N-O bond cleavage of oxime acetates, addition of the radical to ninhydrin and rearrangement via ring expansion.

Direct Enamido C(sp2)?H Diphosphorylation Enabled by a PCET-Triggered Double Radical Relay: Access to gem-Bisphosphonates

Herein we report a novel and straightforward protocol for the construction of valuable gem-BPs by means of proton-coupled electron-transfer (PCET)-triggered enamido C(sp2)?H diphosphorylation. This reaction represents a rare example of realizing the challenging double C?P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves two rounds of PCET-initiated radical relay process.

CuCl2-catalyzed N[sbnd]O bond cleavage of oxime esters: Approach to imidazoheterocycles and furo[3,2-c]chromenyl fused imidazoles

An articulate approach to a diverse set of imidazoheterocycles in good to high yields via a copper-catalyzed aza-annulation of several oxime esters with a group of 2-amino-azaarenes was developed. The above cyclization reaction probably proceeds via a single electron transfer process which embodies a new technique for creating two new C[sbnd]N bonds for imidazole ring synthesis. Gratifyingly, the implementation of this chemistry could be further stretched to the synthesis of a novel class of fused imidazoles bearing a furo[3,2-c]chromene moiety via a sequential C[sbnd]N bond formation, followed by C(sp2)-H functionalization/5-endo-dig-oxacyclization (C[sbnd]C and C[sbnd]O bonds) of in situ produced fused imidazoles with cyclic enynones in the presence of copper(II) as a π-electrophilic Lewis acid catalyst.

Copper(0)/PPh3-Mediated Bisheteroannulations of o-Nitroalkynes with Methylketoximes Accessing Pyrazo-Fused Pseudoindoxyls

A copper(0)/PPh3-mediated cascade bisheteroannulation reaction of o-nitroalkynes with methylketoximes has been developed that provides viable access to a diverse range of pyrazo-fused pseudoindoxyl compounds. Synthetically useful functional groups including sensitive C-I bonds are compatible with this system. Mechanistic studies suggest a reaction cascade involving sequential PPh3-mediated deoxygenative cycloisomerization and copper-catalyzed [3 + 2] pyrazo-annulation.

Merging alkenyl C-H activation with the ring-opening of 1,2-oxazetidines: Ruthenium-catalyzed aminomethylation of enamides

1,2-Oxazetidines have been utilized as formaldimine precursors for the direct aminomethylation of enamides under a Ru(ii) species. By merging alkenyl C-H activation with ring-opening of 1,2-oxazetidines, this efficient protocol provides a facile and novel

SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams

A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.

Visible Light-Promoted Beckmann Rearrangements: Separating Sequential Photochemical and Thermal Phenomena in a Continuous Flow Reactor

The Beckmann rearrangement of oximes to amides typically requires strong acids or highly reactive, hazardous electrophiles and/or elevated temperatures to proceed. A very attractive alternative is the in situ generation of Vilsmeier–Haack reagents, by means of photoredox catalysis, as promoters for the thermal Beckmann rearrangement. Investigation of the reaction parameters for this light-induced method using a one-pot strategy has shown that the reaction is limited by the different temperatures required for each of the two sequential steps. Using a continuous flow reactor, the photochemical and thermal processes have been separated by integrating a flow photoreactor unit at low temperature for the electrophile generation with a second reactor unit, at high temperature, where the rearrangement takes place. This strategy has enabled excellent conversions and yields for a diverse set of oximes, minimizing the formation of side products obtained with the original one-pot method.

Direct access to bis-S-heterocycles via copper-catalyzed three component tandem cyclization using S8 as a sulfur source

A novel strategy for constructing sulfur containing bis-S-heterocyclic compounds from oxime esters/vinyl azide, phenylacetylene/aldehydes and elemental sulfur (S8) has been developed. These transformations show good functional group tolerance. Various bis-S-heterocyclic products were efficiently synthesized from easily prepared or widely commercially available starting materials. In this protocol, S8 successfully served as a two-sulfur atom donor for thiophene and thiazole rings, respectively.

The ruthenium-catalyzed C-H functionalization of enamides with isocyanates: Easy entry to pyrimidin-4-ones

Ruthenium-catalyzed heteroannulation between enamides and isocyanates has been realized as a complementary approach to conventional strategies for the synthesis of pyrimidin-4-ones. High step-A nd atom-economy was achieved for the rapid construction of such privileged scaffolds, which are found in a multitude of pharmaceutical compounds. The generality and practicability of this transformation were reflected by the broad scope of substrates with diverse functional groups, large-scale synthesis, and late-stage diversification.