323-04-6

Usage

Uses

Used in Chemical Synthesis:
4-Fluorobenzaldehyde 2,4-Dinitrophenylhydrazone is used as an intermediate in the synthesis of various organic compounds, particularly those involving the incorporation of fluorine atoms into aromatic systems. Its unique structure allows for selective reactions and functional group transformations, making it a valuable building block in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Analytical Chemistry:
4-Fluorobenzaldehyde 2,4-Dinitrophenylhydrazone is employed as a derivatizing agent in analytical chemistry for the detection and quantification of aldehydes and ketones. The formation of the DNPH derivative enhances the stability and solubility of the analytes, facilitating their separation and analysis by techniques such as high-performance liquid chromatography (HPLC), gas chromatography (GC), or mass spectrometry (MS).
Used in Research and Development:
4-Fluorobenzaldehyde 2,4-Dinitrophenylhydrazone serves as a valuable research tool in the study of fluorinated aromatic compounds and their properties. Its synthesis and reactivity can provide insights into the effects of fluorination on molecular behavior, which is crucial for the design of new materials and the optimization of chemical processes.
Used in Pharmaceutical Industry:
4-Fluorobenzaldehyde 2,4-Dinitrophenylhydrazone is used as a key intermediate in the synthesis of fluorinated drug candidates, which often exhibit improved pharmacokinetic and pharmacodynamic properties compared to their non-fluorinated counterparts. The incorporation of fluorine can enhance the lipophilicity, metabolic stability, and receptor binding affinity of drug molecules, leading to more effective therapeutic agents.
Used in Material Science:
4-Fluorobenzaldehyde 2,4-Dinitrophenylhydrazone can be utilized in the development of novel materials with tailored properties, such as fluorinated polymers, coatings, and adhesives. The introduction of fluorine atoms into the molecular structure can impart unique characteristics, such as increased thermal stability, chemical resistance, and non-stick properties, which are desirable in various industrial applications.

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 459-56-3 4-fluorobenzylic alcohol 

Relevant academic research and scientific papers

Correlation analysis of reactivity in the oxidation of substituted benzyl alcohols by benzimidazolium dichromate - A kinetic and mechanistic aspects

The oxidation of a number of para- and meta-substituted benzyl alcohols by benzimidazolium dichromate (BIDC), in dimethyl sulphoxide, leads to the formation of the corresponding benzaldehydes. The reaction is first order with respect to each BIDC and alcohol. The reaction is catalyzed by hydrogen ions and the dependence has the form kobs = a + b[H+]. The oxidation of [1,1-2H2]benzyl alcohol exhibited the presence of a substantial kinetic isotope effect. The rates of the oxidation of meta-substituted benzyl alcohols correlated best with Taft's σ1 and σR0 constants. The para-substituted compounds exhibited excellent correlation with σ1 and σRBA values. The polar reaction constants are negative. The rate of oxidation of benzyl alcohol was determined in nineteen organic solvents. An analysis of the solvent effect by multiparametric equations indicated the greater importance of the cation-solvating power of the solvents. Suitable mechanisms have been discussed.

Structure-Reactivity correlation in the oxidation of substituted benzaldehydes by tetraethylammonium chlorochromate

Oxidation of 36 monosubstituted benzaldehydes by tetraethylammonium chlorochromate in dimethyl sulphoxide, leads to the formation of corresponding benzoic acids. The reaction is of first order with respect to chlorochromate and aldehydes. The reaction is promoted by H+; the H+ dependence has the form kobs = a + b[H+]. The oxidation of duteriated benzaldehyde exhibits substantial primary kinetic isotope effect. The reaction was studied in 19 different organic solvents and the effect of solvent was analyzed using Taft's and Swain's multiparametric equations. The rates of the oxidation of para- and meta-substituted benzaldehydes showed excellent correlation in terms of Charton's triparametric LDR equation, whereas the oxidation of ortho-substituted benzaldehydes were correlated well with tetraperametric LDRS equation. The oxidation of para-substituted benzaldehydes is more susceptible to the delocalized effect than is the oxidation of ortho- and meta- substituted compounds, which display a greater dependence on the field effect. The positive value of h suggests the presence of an electron-deficient reaction centre in the rate-determining step. The reaction is subjected to steric acceleration by the orthosubstituents. A suitable mechanism has been proposed.

Studies on the kinetics of tripropylammonium fluorochromate oxidation of some aromatic alcohols in non-aqueous media

The oxidation of benzyl alcohol (BnOH) and a few para-substituted benzyl alcohols by tripropylammonium fluorochromate (TriPAFC) in dimethylsulphoxide (DMSO) leads to the formation of corresponding aldehydes. The reaction is first order each in TriPAFC and the alcohols. The reaction is catalysed by hydrogen ions. The hydrogen ion dependence has the form: kobs = a + b[H +]. The oxidation of α α′-dideuterio benzyl alcohol exhibited a substantial primary kinetic isotope effect (kH/k D = 5.45 at 303 K). Oxidation of benzyl alcohol was studied in 19 different organic solvents. The solvent effect has been analysed using Kamlet's and Swain's multiparametric equation. A mechanism involving a hydride ion transfer via chromate ester is proposed.

Kinetics and Mechanism of the Oxidation of Substituted Benzylamines by N-Chlorosuccinimide

The oxidation of ortho-, meta-, and para-substituted benzylamines by N-chlorosuccinimide (NCS), to the corresponding benzaldehydes, is first-order with respect to NCS and the amine.The pH dependence of the reaction rate suggests that the unprotonated benzylamine is the reductant.There is no effect of added succinimide.NCS itself has been postulated as the reactive oxidising species.The oxidation of benzylamine exhibited a substantial primary kinetic isotope effect (kH/kD=6.20).The rates of oxidation of the meta- and para-substituted benzylamines were separately correlated in Taft and Swain's dual substituent parameter equations.For the para-substituted compounds, the best correlation is obtained with ?I and ?R+ values; meta-substituted compounds correlate with ?I and ?R0 values.The reaction constants have negative values.The oxidation rates of the ortho-substituted compounds yield an excellent correlation in a triparametric equation involving Taft's ?I and ?R+ values and Charton's steric parameter, V.A mechanism involving transfer of a hydride ion from the amine to the oxidant in the rate-determining step is proposed.