18440-58-9

Usage

Physical state

Pale yellow solid

Molecular weight

194.63 g/mol

Usage

Reagent in organic synthesis (preparation of heterocyclic compounds and pharmaceuticals)

Role

Synthesis of various hydrazones, potential intermediate in the production of other organic chemicals

Safety precautions

Handle with care, follow appropriate safety guidelines due to reactive nature and potential health hazards.

InChI:InChI=1/C9H9ClN2O/c1-7(13)9(10)12-11-8-5-3-2-4-6-8/h2-6,11H,1H3/b12-9+

Upstream product

• 2684-02-8 benzenediazonium 
• 34959-81-4 ethyl 3-chloro-2,4-dioxopentanoate 
• 64-19-7 acetic acid 
• 127-09-3 sodium acetate 
• 100-34-5 benzene diazonium chloride 
• 78-95-5 chloroacetone 
• 64-17-5 ethanol 
• 127-08-2 potassium acetate 
• 1694-29-7 3-chloropentane-2,4-dione 
• 34885-34-2 phenyldiazonium acetate 
• 62-53-3 aniline 

Downstream Products

• 136515-01-0 1-(2-Methyl-5-phenyl-6-thiophen-2-yl-1,2,5,6-tetrahydro-[1,2,4,5]tetrazin-3-yl)-ethanone 
• 81402-65-5 1-(1-Phenyl-1H-benzo[4,5]imidazo[2,1-c][1,2,4]triazol-3-yl)-ethanone 
• 136515-07-6 1-(2-Methyl-5-phenyl-6-pyridin-2-yl-1,2,5,6-tetrahydro-[1,2,4,5]tetrazin-3-yl)-ethanone 
• 135676-84-5 1-(2-Methyl-5,6-diphenyl-1,2,5,6-tetrahydro-[1,2,4,5]tetrazin-3-yl)-ethanone 
• 118317-97-8 5-Acetyl-2-phenyl-3,4-dihydro-2H-pyrazole-3-carbonitrile 
• 118317-93-4 5-Acetyl-2-phenyl-3,4-dihydro-2H-pyrazole-3-carboxylic acid amide 
• 139130-79-3 1-(6,6-Dimethyl-2-phenyl-2,3-diaza-bicyclo[3.1.0]hex-3-en-4-yl)-ethanone 

Relevant academic research and scientific papers

Synthesis and cytotoxic activity study of novel 2-(Aryldiazenyl)-3-methyl-1h-benzo[g]indole derivatives

A novel series of 2-(aryldiazenyl)-3-methyl-1H-benzo[g]indole derivatives (3a–f) were prepared through the cyclization of the corresponding arylamidrazones, employing polyphosphoric acid (PPA) as a cyclizing agent. All of the compounds (3a–f) were characterized using1H NMR,13C NMR, MS, elemental analysis, and melting point techniques. The synthesized compounds were evaluated for cytotoxic activity against diverse human cancer cell lines by the National Cancer Institute. While all of the screened compounds were found to be cytotoxic at a 10 μM concentration, two of them (2c) and (3c) were subjected to five dose screens and showed a significant cytotoxicity and selectivity.

Design and synthesis of pyrazolo[3,4-d]pyridazine 5,6-dioxides as novel NO-donors

A simple and effective protocol for the synthesis of 2H-pyrazolo[3,4-d]pyridazine 5,6-dioxides includes a transformation of accessible 3,4-diacetyl-5-methyl-1H-pyrazoles into the corresponding 1,4-dioximes followed by their N2O4- mediated oxidative cyclization. All transformations proceed under mild conditions in good to high yields. According to the Griess assay, synthesized 2H-pyrazolo[3,4-d]pyridazine 5,6-dioxides showed promising NO-donor profiles producing NO in a wide range of concentrations.

New fused pyrimidine derivatives with anticancer activity: Synthesis, topoisomerase II inhibition, apoptotic inducing activity and molecular modeling study

A new series of triazolopyrimidines and thiazolopyrimidine hydrobromides was designed and prepared as topoisomerase II inhibitors. Screening of all synthesized compounds was carried out by the National Cancer Institute (NCI) of USA. Activity against 60 hu

Bis-heterocycles. Part I: Tetrahydro-5,5′- bi(1,2,4-triazin-6-ones)

Selected sets of tetrahydro-5,5′-bi(1,2,4-triazines) (1-3) appended with acetyl, benzoyl, and ester moieties at C-3 position and N-1 (p-substituted)phenyl ring have been prepared and characterized by spectral (IR, NMR, MS) data and X-ray diffraction for c

Synthesis and structure-activity relationship; exploration of some potent anti-cancer phenyl amidrazone derivatives

Background: Amidrazones have been reported to have significant anti-tumor properties against several cancer cell lines. Objectives: The current project aims to profile the structure-anticancer activity relationship of phenyl-amidrazons. Methods: Fifteen p

Synthesis and fluorescent behaviour of 2-aryl-4,5-dihydro-1H-1,2,4-triazoles

A series of new 4,5-dihydro-1H-1,2,4-triazoles was synthesized from amidrazones and acetylenedicarboxylic acid esters in the presence of pyridine in toluene. The synthesized compounds were characterized by 1H, 13C NMR, FT-IR spectral analyses and XRD data

Spectral characterization, CT-DNA binding, DFT/B3LYP, molecular docking and antitumor studies for new nano-sized VO(II)-hydrazonoyl complexes

New hydrazonoyl chloride derivatives were prepared and characterized. Their VO(II) complexes were isolated after adjusting reaction medium to slightly basic by 0.5?g acetate. Neutral tridentate mode is a general coordination feature of ligands towards bin

Synthesis, in vitro and in Silico studies of some novel 5-nitrofuran-2-yl hydrazones as antimicrobial and antitubercular agents

In this study, we synthesized two series of novel 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e in addition to a third series of thiophene-2-carbohydrazides 23a-g to develop potent antimicrobial and/or antitubercular agents. The newly synthesized compounds were evaluated in vitro for their antimicrobial and antimycobacterial activities. Most of the 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e displayed variable activity against Aspergillus fumigates, Staphylococcus aureus, Streptococcus pneumonia, Bacillis subtilis, Salmonella typhimurium, Klebsiella pneumonia, Escherichia coli and Mycobacterium tuberculosis. The sulfonamide derivative 21f exhibited superior potency and broad-spectrum antimicrobial activity with minimum inhibitory concentration (MIC)=0.06-0.98 μg/mL and antimycobacterial activity with MIC=3.9 μg/mL. The 5-nitrofuran-2-carbohydrazides 21a, b, g, h and 22a-c exhibited significant antibacterial activity with MIC values in the range of 0.12-7.81 μg/mL. The significances of the 5-nitrofuran moiety and sulfonamide function were explored via the structure-activity relationship (SAR) study. In addition, docking studies revealed that the p-amino benzoic acid (PABA) and binding pockets of the dihydropteroate synthase (DHPS) were successfully occupied by compound 21f. Furthermore, two quantitative structure-activity relationship (QSAR) models were built to explore the structural requirements which controlled the activity.

Methyl 3-cyclopropyl-3-oxopropanoate in the synthesis of heterocycles having a cyclopropyl substituent

Reactions of methyl 3-cyclopropyl-3-oxopropanoate with chloroacetone and ammonia, benzaldehyde and ammonia, and benzoquinone gave, respectively, methyl 2-cyclopropyl-5-methyl-1H-pyrrole-3-carboxylate, dimethyl 2,6-dicyclopropyl-4- phenyl-1,4-dihydropyridi

Synthesis, antitumor activity, and electrochemical behavior of some piperazinyl amidrazones

New piperazinyl amidrazones have been synthesized by direct interaction of the corresponding aryl hydrazones with the appropriate piperazine. On the basis of preliminary screening data for these new compounds, the antitumor activity of 1-(4-methylpiperazi