658-27-5

Usage

Uses

Used in Pharmaceutical Industry:
(3-FLUOROPHENYL)HYDRAZINE is used as a building block for the synthesis of various pharmaceutical compounds, playing a crucial role in the development of new drugs.
Used in Organic Synthesis:
(3-FLUOROPHENYL)HYDRAZINE is used as a reagent in the preparation of other organic compounds, particularly through its ability to react with carbonyl compounds to form hydrazones, which are valuable intermediates in organic chemistry.
Used in Agrochemicals:
(3-FLUOROPHENYL)HYDRAZINE has potential applications in the field of agrochemicals, where it may be utilized in the development of new pesticides or other agricultural chemicals.
Used as a Precursor for Biologically Active Molecules:
(3-FLUOROPHENYL)HYDRAZINE can be used as a precursor for the synthesis of various biologically active molecules, contributing to the advancement of medical and biological research.
It is important to handle (3-FLUOROPHENYL)HYDRAZINE with care, as it is toxic and can cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be taken during its use and manipulation.

Upstream product

• 372-19-0 meta-fluoroaniline 
• 1073-06-9 3-fluorobromobenzene 

Downstream Products

• 404-69-3 (E)-ethyl 2-(2-(3-fluorophenyl)hydrazin-1-ylidene)propanoate 
• 635325-08-5 4-[N'-(3-fluoro-phenyl)-hydrazino]-1-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 635325-89-2 4-[N'-(3-fluoro-phenyl)-hydrazino]-1-methyl-6-pyridin-3-yl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 635325-91-6 6-(5-bromo-pyridin-3-yl)-4-[N'-(3-fluoro-phenyl)-hydrazino]-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid methyl ester 
• 635325-92-7 6-(3,5-dichloro-phenyl)-4-[N'-(3-fluoro-phenyl)-hydrazino]-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester 
• 586353-31-3 1-(3-fluoro-phenyl)-1,4,5,6-tetrahydro-1,2,6,7-tetraaza-as-indacene-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Fluorine-substituted phenyl pyrazole amide derivative, and preparation method and application thereof

The invention relates to a fluorine-substituted phenyl pyrazole amide derivative with insecticidal activity as shown in a general formula (I), and a preparation method and application thereof. On the basis of an existing phenyl pyrazole amide compound, fl

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.

Preparation method for 3-fluorophenylhydrazine hydrochloride

The invention relates to a preparation method for 3-fluorophenylhydrazine hydrochloride. The preparation method comprises the following steps: diazotization, reduction, purification and salt formation. During diazotization and reduction, concentrated hydrochloric acid enables a reaction solution to maintain highly acidic, so smooth and complete reaction is guaranteed. In the step of reduction, zinc dust-concentrated hydrochloric acid is used as a reducing agent to replace sodium hyposulfite, sodium bisulfate, stannous chloride-hydrochloric acid, etc., and the zinc dust-concentrated hydrochloric acid is good in reducing property and high in yield, shortens reaction time, enables impurities like zinc hydroxide produced after the reaction to be easy to remove and allows produced 3-fluorophenylhydrazine hydrochloride to be low in impurity content and high in purity. In the step of salt formation, acetone is used for leaching, so product purity is improved and product appearance is guaranteed. The preparation method is stable and reliable in process and easy to operate; and produced 3-fluorophenylhydrazine hydrochloride is high in purity (no less than 99% according to the results of content measurement via high performance liquid chromatography), has a yield of no less than 39% and completely meets market demands for 3-fluorophenylhydrazine hydrochloride.

Preparation method of 3-fluorophenylhydrazine sulfate

The invention relates to a preparation method of 3-fluorophenylhydrazine sulfate. The method includes the steps of diazotization, reduction, purification and salt formation. In the steps of diazotization and reduction, concentrated hydrochloric acid is em

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.

Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi

A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.

Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400

An efficient and convenient method for the synthesis of aryl hydrazines is described via copper-catalyzed cross-coupling of aryl halides with aqueous hydrazine in PEG-400. This protocol is applicable to both electron-deficient and electron-rich aryl iodides and bromides, and even to sterically hindered substrates, giving aryl hydrazines in good to excellent yields.

PYRIDAZINONE DERIVATIVES

The present invention is concerned with novel pyridazinone derivatives of formula (I) wherein R1, R2, R3 and R4 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit PDE10A and can be used as medicaments

Synthesis and adenosine receptor affinity of a series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine

Pyrazolo[3,4-d]pyrimidines are pyrazolo analogues of purines. They have been shown to be a general class of compounds which exhibit A1 adenosine receptor affinity. Two series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine have been synthesized. The first involved substitution of the N1-position while the second involved substitution of the N5-position. Both alkyl and aryl substituents were examined. All compounds were tested for A1 adenosine receptor affinity by using a (R)-[3H]-N6-(phenylisopropyl)adenosine binding assay. The 3-chlorophenyl group showed the greatest activity in the N1-position and the butyl group produced the greatest activity in the N5-position. Combination of the best substituent in each of these positions enhanced the overall activity. The most potent compound was 4-amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one with an IC50 of 6.4 X 10-6 M. Selectivity at the receptor subclasses was examined by performing an A2 adenosine receptor affinity assay with [3H]CGS 21680. This series of compounds were slightly less potent at A2 receptors. 4-Amino-5-N-butyl-1-(3-chlorophenyl)-1H-pyrazolo[3,4-d] pyrimidin-6(5H)-one was the most potent compound with an IC50 of 19.2 X 10-6 M.