10449-07-7

Usage

Uses

Used in Pharmaceutical Industry:
(2-CHLOROPHENYL)HYDRAZINE HYDROCHLORIDE is used as a research reagent for the preparation of halogen-substituted phenylhydrazine derivatives. These derivatives exhibit antifungal properties, making them valuable in the development of new antifungal drugs and treatments.
Used in Organic Synthesis:
(2-CHLOROPHENYL)HYDRAZINE HYDROCHLORIDE serves as an intermediate in the synthesis of various organic compounds. Its unique structure allows for further chemical reactions, leading to the formation of a wide range of products with different applications in various industries.
Used in Chemical Research:
As a research reagent, (2-CHLOROPHENYL)HYDRAZINE HYDROCHLORIDE is utilized in chemical research to study the properties and reactions of phenylhydrazine derivatives. This helps in understanding their potential applications and developing new methods for their synthesis and modification.

InChI:InChI=1/C6H7ClN2/c7-5-3-1-2-4-6(5)9-8/h1-4,9H,8H2

Upstream product

• 17333-83-4 2-chlorobenzenediazonium 
• 952-53-4 1,3-diphenyl-2,3-diazaprop-2-en-1-one 
• 1956-97-4 2-chlorobenzenediazonium tetrafluoroborate 
• 7647-01-0 hydrogenchloride 
• 79984-70-6 N’-(2-chlorophenyl)benzohydrazide 
• 857595-49-4 o-chloronitroaniline 
• 95-51-2 o-chloroaniline 
• 50-81-7 ascorbic acid 
• 89-90-7 2-chlorobenzenediazonium chloride 

Downstream Products

• 107915-28-6 4-[2-(2-chloro-phenyl)-5-methyl-2H-pyrazol-3-yl]-pyridine 
• 20629-90-7 1-(2-chlorophenyl)-3-methyl-5-pyrazolone 
• 105197-27-1 2-(2-chloro-phenyl)-4-phenyl thiosemicarbazide 
• 108871-21-2 N-(5-chloro-2-nitro-phenyl)-N'-(2-chloro-phenyl)-hydrazine 
• 64096-89-5 5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile 
• 90533-17-8 (2-chloro-phenylhydrazono)-malonic acid 
• 42141-49-1 3-(2-chloro-phenylhydrazono)-butyronitrile 
• 100859-33-4 (2-chloro-phenyl)-sulfinyl-hydrazine 
• 134468-95-4 (2-Chloro-phenyl)-(3,4,6,7,8,9-hexahydro-2H-quinolizin-1-yl)-diazene 
• 1027028-91-6 4-[N'-(2-Chloro-phenyl)-hydrazino]-quinoline-3-carboxylic acid ethyl ester 
• 103973-45-1 deoxybenzoin o-chlorophenylhydrazone 

Relevant academic research and scientific papers

Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy

Serine, the source of the one-carbon units essential for de novo purine and deoxythymidine synthesis plays a crucial role in the growth of cancer cells. Phosphoglycerate dehydrogenase (PHGDH) which catalyzes the first, rate-limiting step in de novo serine biosynthesis has become a promising target for the cancer treatment. Here we identified H-G6 as a potential PHGDH inhibitor from the screening of an in-house small molecule library based on the enzymatic assay. We adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest. Collectively, our results suggest that b36 is a novel PHGDH inhibitor, which could be a promising modulator to reprogram the serine synthesis pathway and might be a potential anticancer lead worth further exploration.

Azologization of serotonin 5-HT3 receptor antagonists

The serotonin 5-hydroxytryptamine 3 receptor (5-HT3R) plays a unique role within the seven classes of the serotonin receptor family, as it represents the only ionotropic receptor, while the other six members are G protein-coupled receptors (GPCRs). The 5-HT3 receptor is related to chemo-/radiotherapy provoked emesis and dysfunction leads to neurodevelopmental disorders and psychopathologies. Since the development of the first serotonin receptor antagonist in the early 1990s, the range of highly selective and potent drugs expanded based on various chemical structures. Nevertheless, on-off-targeting of a pharmacophore’s activity with high spatiotemporal resolution as provided by photopharmacology remains an unsolved challenge bearing additionally the opportunity for detailed receptor examination. In the presented work, we summarize the synthesis, photochromic properties and in vitro characterization of azobenzene-based photochromic derivatives of published 5-HT3R antagonists. Despite reported proof of principle of direct azologization, only one of the investigated derivatives showed antagonistic activity lacking isomer specificity.

Method for synthesizing 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone

The invention discloses a method for synthesizing 1-(2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-1,2,4-triazole-5-ketone. The method comprises the following steps: with o-chloroaniline as a raw material, carrying out diazotization, reduction and salific

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.

Regioselective radical arylation of anilines with arylhydrazines

Substituted 2-aminobiphenyls have been prepared from arylhydrazines and anilines via radical arylation reactions under simple oxidative conditions. The strong directing effect of the free and unprotonated amino functionality leads to high regioselectivities, and anilines have been shown to be significantly better aryl radical acceptors than nitrobenzenes or phenyl ethers. The methodology is also applicable to phenols, which react best as phenolates under strongly basic conditions. Finally, radical arylation reactions of anilines and anilinium salts under various conditions have for the first time demonstrated that regioselectivity can also be controlled through the rearomatization step and that the addition of an aryl radical to a substituted benzene might even be reversible.

Photoinduced cleavage of N-N bonds of aromatic hydrazines and hydrazides by visible light

A photocatalytic system involving [Ru(bpyrz)(PFH, visible light, and air has been developed for cleavage of the N-N bonds of hydrazines and hydrazides. This catalytic system is generally effective for N,N-disubstituted hydrazine and hydrazide derivatives, including arylhydrazides, N-alkyl-N-arylhydrazines, and N,N-diarylhydrazines. The utility of this cleavage reaction has been demonstrated by synthesizing a variety of secondary aromatic amines. Georg Thieme Verlag Stuttgart ? New York.

Preparation of sodium-hydrogen exchanger type-1 inhibitors

This invention relates to methods of preparing sodium-hydrogen exchanger type 1 (NHE-1) inhibitors of formula I′ 1intermediates of the NHE-1 inhibitors and a new almost colorless form of the NHE-1 inhibitor N-(5-cyclopropyl-1-quinolin-5-yl-1H-pyrazole-4-carbonyl)-guanidine.

Novel chemoselective reduction of aryldiazonium fluoroborates with Zn- NiCl2·6H2O-THF

Substituted aryldiazonium fluoroborates are selectively reduced to the corresponding phenylhydrazines by using Zn-NiCl2·6H2O in THF as a reducing agent.

Selective reduction of aryl diazonium fluoroborates

Substituted aryl diazonium fluoroborates have been selectively reduced to the corresponding phenylhydrazines by using borohydride exchange resin (BER).

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.