80605-38-5

Usage

Uses

Used in Analytical Chemistry:
(4-Nitrophenyl)acetone oxime is used as a reagent for its ability to react with aldehydes and ketones, forming oximes. This reaction is significant in analytical chemistry as it aids in the detection and identification of these compounds.
Used in Organic Synthesis:
In the field of organic synthesis, (4-Nitrophenyl)acetone oxime is used as a precursor to produce oximes. These oximes serve as important intermediates in the synthesis of various organic compounds.
Used in Pharmaceutical and Biological Research:
(4-Nitrophenyl)acetone oxime is utilized in pharmaceutical and biological research due to its potential as a chelating agent. Its ability to form complexes with metal ions makes it a valuable tool in these fields.
Used in Laboratory Settings:
As a moderately hazardous compound, (4-Nitrophenyl)acetone oxime is used in laboratory settings with proper safety measures. Its handling requires care to ensure the safety of researchers and the integrity of experiments.

Upstream product

• 5332-96-7 1-(4-nitrophenyl)propan-2-one 
• 50434-36-1 4-nitrophenylacetyl chloride 

Downstream Products

• 80605-48-7 p-Nitrobenzylmethylketonoximpikrat 
• 1309380-87-7 C₁₉H₁₆N₂O₅S 

Relevant academic research and scientific papers

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.

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.