1454-65-5

Usage

Uses

Used in Pharmaceutical Synthesis:
(4-Chlorophenyl)acetone oxime is used as an intermediate in the pharmaceutical industry for the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of a range of different compounds with potential therapeutic applications.
Used in Chemical Weapon Antidotes:
(4-Chlorophenyl)acetone oxime is studied for its potential as a cholinesterase reactivator, which could be used to counteract the effects of nerve agents and other chemical weapons. Its ability to reactivate enzymes inhibited by these toxic substances makes it a valuable compound in the development of antidotes.
Used in Industrial Applications:
Due to its antioxidant properties, (4-Chlorophenyl)acetone oxime is also useful in various industrial applications. Antioxidants are essential in preventing the oxidation of other materials, which can lead to degradation or spoilage. (4-CHLOROPHENYL)ACETONE OXIME's antioxidant capabilities make it a valuable asset in industries where preserving the quality and longevity of products is crucial.

Upstream product

• 710-20-3 1-chloro-4-(2-nitropropenyl)benzene 
• 1163136-86-4 1-chloro-4-(2-nitro-1(Z)-propenyl)benzene 
• 5586-88-9 1-(4-chlorophenyl)propan-2-one 
• 25026-34-0 4-chlorophenacetyl chloride 

Downstream Products

• 1262155-46-3 C₁₉H₁₆ClNO₃S 
• 1061288-55-8 3β-(4-methylphenyl)-2β-[3'-(4-chlorobenzyl)isoxazol-5-yl]tropane 
• 1061288-74-1 3β-(4-methylphenyl)-2β-[3'-methyl-4'-(4-chlorophenyl)isoxazol-5-yl]tropane 
• 1061288-52-5 3β-(4-chlorophenyl)-2β-[3'-(4-chlorobenzyl)isoxazol-5-yl]tropane 
• 1061288-71-8 3β-(4-chlorophenyl)-2β-[3'-methyl-4'-(4-chlorophenyl)isoxazol-5-yl]tropane 
• 63-93-4 N-hydroxy-1-methyl-2-(4-chlorophenyl)ethanamine 
• 64-12-0 p-Chloroamphetamine 
• 80605-47-6 p-Chlorbenzylmethylketonoximpikrat 

Relevant academic research and scientific papers

Modular 2,3-diaryl-2: H -azirine synthesis from ketoxime acetates via Cs2CO3-mediated cyclization

A modular 2H-azirine synthesis from ketoxime acetates via Cs2CO3-mediated cyclization has been developed. The reaction utilizes easily available starting materials and provides a general synthetic route to 2,3-diaryl-2H-azirines in good to excellent yields under mild conditions, which is complementary to the conventional approaches for the synthesis of 2H-azirines. A gram-scale reaction was performed to demonstrate the scale-up applicability of this synthetic method. Importantly, 2H-azirines can be efficiently converted to various azaheterocycles.

RhII-catalyzed [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles

RhII-catalyzed intermolecular [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles is disclosed, in which a series of fully functionalized pyrroles is produced via rhodium azavinyl carbene intermediates. A distinct feature of this reaction is that the azavinyl carbene serves as a [2 C] equivalent, instead of as [1 C] or aza-[3 C] synthons, which have been reported previously in cyclopropanations and [3 + n] cycloadditions. Moreover, this methodology has also been successfully applied in the total synthesis of URB447 as well as the formal synthesis of Atorvastatin (Lipitor).

Gold-Catalyzed Intermolecular Nitrene Transfer from 2H-Azirines to Ynamides: A Direct Approach to Polysubstituted Pyrroles

(Chemical Equation Presented). An effective gold-catalyzed intermolecular nitrene transfer by the reaction of 2H-azirines and ynamides is reported, which provides highly substituted pyrroles in a straightforward manner. This transformation proceeds under mild conditions and gives the polysubstituted pyrroles in good-to-excellent yields. Preliminary results indicate that a nongold carbenoid pathway is preferred for current pyrrole synthesis.

Dynamic path bifurcation in the Beckmann reaction: Support from kinetic analyses

The reactions of oximes to amides, known as the Beckmann rearrangement, may undergo fragmentation to form carbocations + nitriles when the migrating groups have reasonable stability as cations. The reactions of oxime sulfonates of 1-substituted-phenyl-2-propanone derivatives (7-X) and related substrates (8-X, 9a-X) in aqueous CH3CN gave both rearrangement products (amides) and fragmentation products (alcohols), the ratio of which depends on the system; the reactions of 7-X gave amides predominantly, whereas 9a-X yielded alcohols as the major product. The logk-logk plots between the systems gave excellent linear correlations with slopes of near unity. The results support the occurrence of path bifurcation after the rate-determining TS of the Beckmann rearrangement/fragmentation reaction, which has previously been proposed on the basis of molecular dynamics simulations. It was concluded that path-bifurcation phenomenon could be more common than thought and that a reactivity-selectivity argument based on the traditional TS theory may not always be applicable even to a well-known textbook organic reaction.

REDUCTIVE CONVERSION OF NITRO ALKENES TO KETONES AND/OR OXIMES IN AN AQUEOUS HClO4-CH2Cl2-DIOXANE-(Pb) SYSTEM

Electrochemical and chemical reduction of nitro alkenes in an aqueous HClO4-CH2Cl2-dioxane-(Pb) system afforded ketones and oximes in good yields, each of which can be obtained selectively by treating with either aqueous formaldehyde or hydroxylamine as a proper workup process, respectively.

Alkylwanderungen bei Sextettumlagerungen

The migration aptitude of alkyl groups in the Beckmann-, the Criegee-, and the isonitrile-nitrile rearrangements were investigated.The relative rearrangement rates of substituted benzyl groups are an expression of the charge on the migrating carbon at transition state.From the relative rates of migration of exo- and endo-2-norbornyl groups the geometrical changes at the migrating carbon is estimated.Finally, the different influence of α-branching in the migrating group is discussed for these and some other rearrangements.