371-14-2

Usage

Uses

Used in Pharmaceutical Industry:
4-FLUOROPHENYLHYDRAZINE is used as a versatile reactant for the synthesis of various pharmaceutical compounds. Its unique structure allows it to participate in domino synthesis of indoles, which are important in the development of drugs targeting a wide range of medical conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-FLUOROPHENYLHYDRAZINE is used as a key intermediate in the production of various organic compounds. Its reactivity with terminal alkynes, facilitated by zinc-promoted hydrohydrazination, enables the efficient synthesis of complex molecules with potential applications in various industries.
Used in Research and Development:
4-FLUOROPHENYLHYDRAZINE is also utilized in research and development settings, where its unique properties and reactivity are harnessed to explore new synthetic pathways and develop novel compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C6H7FN2/c7-5-1-3-6(9-8)4-2-5/h1-4,9H,8H2

Upstream product

• 371-40-4 4-fluoroaniline 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 137273-08-6 N'-(4-Fluoro-phenyl)-hydrazinecarboxylic acid 2,2,2-trichloro-ethyl ester 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 61161-10-2 N-(4-fluorophenyl)-nitramine 

Downstream Products

• 525-16-6 2-(4-fluoro-phenyl)-4-isopropylidene-5-methyl-2,4-dihydro-pyrazol-3-one 
• 368-22-9 salicylaldehyde-(4-fluoro-phenylhydrazone) 
• 7650-45-5 D-arabino-[2]hexosulose-bis-(4-fluoro-phenylhydrazone) 
• 576-16-9 5-fluorotryptamine 
• 399-72-4 5-fluoro-2-methyl-1H-indole 
• 125689-47-6 bis-(4-fluoro-phenyl)-antimony ⁽³⁺⁾; tris chloride 
• 16600-00-3 3-methyl-3H-benzothiazol-2-one (4-fluoro-phenyl)-hydrazone 
• 54941-97-8 (20Ξ)-2'-(4-fluoro-phenyl)-17,20;20,21-bis-methanediyldioxy-16α-methyl-2'H-pregn-4-eno[3,2-c]pyrazol-11β-ol 
• 1961-56-4 (20Ξ)-9-fluoro-2'-(4-fluoro-phenyl)-17,20;20,21-bis-methanediyldioxy-16α-methyl-2'H-pregn-4-eno[3,2-c]pyrazol-11-one 
• 324-74-3 4-fluoro-biphenyl 
• 134468-97-6 (4-Fluoro-phenyl)-(3,4,6,7,8,9-hexahydro-2H-quinolizin-1-yl)-diazene 
• 130020-27-8 6-Fluoro-3-[(4-fluoro-phenyl)-hydrazono]-1,3-dihydro-indol-2-one 
• 137695-80-8 4-benzyl-2-(p-fluorophenyl)-3-hydroxy-2H-pyrazolo[4,3-c]isoquinolinium hydroxide 
• 143035-15-8 3-{1-[(4-Fluoro-phenyl)-hydrazono]-ethyl}-4-hydroxy-6-methyl-pyran-2-one 

Relevant academic research and scientific papers

Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine

In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.

Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine

Reported here is the Pd-catalyzed C–N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex.

Synthesis, insecticidal activities, and structure-activity relationship of phenylpyrazole derivatives containing a fluoro-substituted benzene moiety

Fluorinated organic compounds represent a growing and important family of commercial chemicals. Introduction of fluorine into active ingredients has become an effective way to develop modern crop protection products. Given the particular properties of fluorine and high efficiency and selectivity of diamide insecticides, we designed and synthesized 27 anthranilic diamides analogues containing fluoro-sustituted phenylpyrazole. A preliminary bioassay indicated that most target compounds exhibited good biological activity against Mythimna separata and Plutella xylostella. Compound IIIf containing a 2,4,6-trifluoro-substituted benzene ring showed 43% insecticidal activity against M. separata at 0.1 mg L-1, while the control chlorantraniliprole was 36%. The activity of IIIe against P. xylostella at 10-5 mg L-1 was 94%, compared with that of the control being 70%. Thus, introduction of fluorine into diamide insecticides was useful for increasing activity. Insect electrophysiology studies showed that the calcium concentration in the nerve cells of third M. separata larvae was elevated by IIIf, which further confirmed that ryanodine receptor (RyR) was its potential target.

PROCESS FOR THE SYNTHESIS OF ARYL HYDRAZINES

The invention relates to a process for the synthesis of aryl hydrazinesof formula I or a salt thereof, which process comprises subjecting an arene of formula II to a coupling reaction with hydrazine or a derivative thereof, wherein the coupling reaction is conducted in the presence of a catalyst comprising palladium and a diphosphine ligand, wherein the phosphorus atoms are connected through two, three, four, or five atoms selected from car- bon, nitrogen, oxygen or iron, and in which the non-connecting phosphorus substituents are C1- C 10-alkyl or C3-C10-cycloalkyl, wherein the amount of Pd used is up to 0.5 mol-% relative to the amount of arene of formula II; and a base.

Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines

In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2-b]pyridazine was achieved with a good yield.

Preparation method of 4-fluorophenylhydrazine hydrochloride

The invention relates to a preparation method of 4-fluorophenylhydrazine hydrochloride. The preparation method comprises the steps of diazotization, reduction, purification and salification. In the steps of diazotization and reduction, reaction liquid is kept at strong acidity with concentrated hydrochloric acid to guarantee successful and complete reaction; in the reduction step, zinc powder-concentrated hydrochloric acid is used as a reducing agent and replaces sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric acid and the like, so that the reducing property is high, the yield is high, and the reaction time is shortened; impurities, such as zinc hydroxide, which are generated after reaction are convenient to remove, so that the number of product impurities is small, and the purity is high; in the salification step, leaching is carried out with acetone, so that the purity of a product is improved, and the appearance of the product is guaranteed. The preparation method is stable and reliable in process, easy to operate and high in product purity (the content measured based on high performance liquid chromatography is greater than or equal to 99 percent); the yield is greater than or equal to 39 percent, so that the requirement of the market for the 4-fluorophenylhydrazine hydrochloride can be completely met.

Preparation method for 4-fluorophenylhydrazine phosphate

The invention relates to a preparation method for 4-fluorophenylhydrazine phosphate. The preparation method comprises the steps of diazotization, reduction, purification and salification. In the steps of diazotization and reduction, concentrated hydrochloric acid is adopted for maintaining a reaction liquid in strong acidity, and guaranteeing smooth and complete reaction. In the step of reduction, zinc powder-concentrated hydrochloric acid is adopted as a reducing agent for replacing sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric acid and the like, the reducing property is good, the yield coefficient is high, the reaction time is shortened, impurities such as zinc hydroxide generated after reaction can be removed conveniently, the product impurities are small, and the purity is high. In the step of salification, acetone is adopted for elution, the product purity is increased, and the product appearance is guaranteed. According to the preparation method, the process is stable and reliable, operation is easy, the product purity is high (the content of the 4-fluorophenylhydrazine phosphate is measured through high performance liquid chromatography and is no smaller than 99.2%), the yield coefficient is no smaller than 42%, and the market demand for the 4-fluorophenylhydrazine phosphate can be fully met.

Preparation method of 4-fluorophenylhydrazine oxalate

The invention relates to a preparation method of 4-fluorophenylhydrazine oxalate. The preparation method comprises the steps of diazotization, reduction, purification and salification. In the steps of diazotization and reduction, reaction liquid is kept at strong acidity with concentrated hydrochloric acid to guarantee successful and complete reaction; in the reduction step, zinc powder-concentrated hydrochloric acid is used as a reducing agent and replaces sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric acid and the like, so that the reducing property is high, the yield is high, and the reaction time is shortened; impurities, such as zinc hydroxide, which are generated after reaction are convenient to remove, so that the number of product impurities is small, and the purity is high; in the salification step, leaching is carried out with acetone, so that the purity of a product is improved, and the appearance of the product is guaranteed. The preparation method is stable and reliable in process, easy to operate and high in product purity (the content measured based on high performance liquid chromatography is greater than or equal to 99.2 percent); the yield is greater than or equal to 42 percent, so that the requirement of the market for the 4-fluorophenylhydrazine oxalate can be completely met.

Preparation method for 4-fluorophenylhydrazine sulfate

The invention relates to a preparation method for 4-fluorophenylhydrazine sulfate. The preparation method comprises the steps of diazotization, reduction, purification and salification. In the steps of diazotization and reduction, concentrated hydrochloric acid is adopted for maintaining a reaction liquid in strong acidity, and guaranteeing smooth and complete reaction. In the step of reduction, zinc powder-concentrated hydrochloric acid is adopted as a reducing agent for replacing sodium thiosulfate, sodium hydrogen sulfite, stannous chloride-hydrochloric acid and the like, the reducing property is good, the yield coefficient is high, the reaction time is shortened, impurities such as zinc hydroxide generated after reaction can be removed conveniently, the product impurities are small, and the purity is high. In the step of salification, acetone is adopted for elution, the product purity is increased, and the product appearance is guaranteed. According to the preparation method, the process is stable and reliable, operation is easy, the product purity is high (the content of the 4-fluorophenylhydrazine sulfate is measured through high performance liquid chromatography and is no smaller than 99.1%), the yield coefficient is no smaller than 42%, and the market demand for the 4-fluorophenylhydrazine sulfate can be fully met.

Synthesis and biological evaluation of 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives as potential c-met inhibitors

Six series of novel 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives conjugated with aza-aryl formamide/amine scaffords were designed and synthesized through a structure-based molecular hybridization approach. The target compounds were evaluated for c-Met kinase inhibitory activities and cytotoxicity against four cancer cell lines (HT-29, A549, MKN-45 and MDA-MB-231) in vitro. Most compounds exhibited moderate to excellent potency, and the most promising candidate 26c (c-Met kinase IC50 = 8.2 nM) showed a 4.7-fold increase in cytotoxicity against c-Met-addicted MKN-45 cell line in vitro (IC50 = 3 nM), superior to that of Foretinib (IC50 = 23 nM). The preliminary structure-activity relationship indicated that a 1H-benzo [e] [1,3,4]thiadiazine-3-carboxamide-4,4-dioxide moiety as linker contributed to the antitumor potency.