619-27-2

Usage

Uses

Used in Chemical Synthesis:
3-Nitrophenylhydrazine is used as a reagent for oxidative coupling reactions with thiols, which is crucial for the production of intricate organic molecules. This application is particularly valuable in the field of organic chemistry, where the creation of complex molecules is essential for various purposes, including pharmaceutical development and material science.
Used in Research:
In addition to its practical applications in chemical synthesis, 3-Nitrophenylhydrazine is also employed as a research tool. It can be used to study the properties and reactions of thiols, as well as to investigate the mechanisms of oxidative coupling reactions. This contributes to a deeper understanding of chemical processes and can lead to the development of new synthetic methods and applications in various industries.

InChI:InChI=1/C6H7N3O2/c7-8-5-2-1-3-6(4-5)9(10)11/h1-4,8H,7H2

Upstream product

• 16278-29-8 3-nitrobenzenediazonium 
• 2028-76-4 3-nitrophenyldiazonium chloride 
• 99-09-2 3-nitro-aniline 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 586-36-7 3-nitrophenyldiazonium tetrafluoroborate 

Downstream Products

• 97031-85-1 phthalic acid mono-[N'-(3-nitro-phenyl)-hydrazide] 
• 339553-17-2 cyclohexanone-(3-nitro-phenylhydrazone) 
• 20576-92-5 benzaldehyde 3-nitrophenylhydrazone 
• 79984-72-8 1-(3-nitro-phenyl)-4-phenyl thiosemicarbazide 
• 859960-93-3 2-(3-nitro-phenyl)-4-phenyl thiosemicarbazide 
• 107922-76-9 vanillin-(3-nitro-phenylhydrazone) 
• 23622-32-4 acetaldehyde-(3-nitro-phenylhydrazone) 
• 134271-93-5 (E)-1-(3-nitrophenyl)-2-propylidenehydrazine 
• 116029-99-3 (3-nitro-phenyl)-sulfinyl-hydrazine 
• 398998-44-2 cyclopentanone-(3-nitro-phenylhydrazone) 
• 7746-58-9 acetophenone-(3-nitro-phenylhydrazone) 
• 40485-50-5 pentan-3-one-(3-nitro-phenylhydrazone) 
• 18492-23-4 butan-2-one-(3-nitro-phenylhydrazone) 

Relevant academic research and scientific papers

Novel Anthranilic Diamide Scaffolds Containing N-Substituted Phenylpyrazole as Potential Ryanodine Receptor Activators

To discover potent insecticides targeting ryanodine receptors (RyRs), a series of novel anthranilic diamides analogues (12a-12u) containing N-substituted phenylpyrazole were designed and synthesized. These compounds were characterized by 1H NMR, 13C NMR, and HRMS, and the structure of compound 12u was confirmed by X-ray diffraction. Their insecticidal activities indicated that these compounds displayed moderate to excellent activities. In particular, 12i showed 100 and 37% larvicidal activities against oriental armyworm (Mythimna separata) at 0.25 and 0.05 mg L-1, equivalent to that of chlorantraniliprole (100%, 0.25 mg L-1; and 33%, 0.05 mg L-1). The activity of 12i against diamondback moth (Plutella xylostella) was 95% at 0.05 mg L-1, whereas the control was 100% at 0.05 mg L-1. The calcium-imaging technique experiment results showed that the effects of 12i on the intracellular calcium ion concentration ([Ca2+]i) in neurons were concentration-dependent. After the central neurons of Helicoverpa armigera were dyed by loading with fluo-5N and treated with 12i, the free calcium released in endoplasmic reticulum indicated the target of compound 12i is RyRs or IP3Rs. The activation of RyRs by natural ryanodine completely blocked the calcium release induced by 12i, which indicated that RyRs in the central neurons of H. armigera third-instar larvae is the possible target of compound 12i.

Synthesis and biological evaluation of some new aryl pyrazol-3-one derivatives as potential hypoglycemic agents

Several new aryl substituted pyrazol-3-one 3 derivatives were prepared by the reaction of substituted phenyl hydrazine 1 with diethylethoxymethylene malonate (DEEM) 2. The compounds were synthesized by Michael addition reaction, which is a nucleophilic addition of enolate anions to the carbon-carbon double bond of α,β-unsaturated carboxylic acid derivatives. All the compounds were characterized by UV, IR and NMR spectroscopy and tested for hypoglycemic activity on alloxan induced diabetic rats. Among the tested compounds ethyl-2-para nitrophenyl-2,3-dihydro-1H-pyrazol-3-one-4-carboxylate 3c and ethyl-2-meta nitrophenyl-2,3-dihydro-1H-pyrazol-3-one-4-carboxylate 3d are identified as potent hypoglycemic agents and their activities are comparable with the standard drug metformin.

De novo design and synthesis of HIV-1 integrase inhibitors

Existing AIDS therapies are out of reach for most HIV-infected people in developing countries and, where available, they are limited by their toxicity and their cost. New anti-HIV agents are needed urgently to combat emerging viral resistance and reduce the side effects associated with currently available drugs. Toward this end, LeapFrog, a de novo drug design program was used to design novel, potent, and selective inhibitors of HIV-1 integrase. The designed compounds were synthesized and tested for in vitro inhibition of HIV-1 integrase. Out of the 25 compounds that were designed, and synthesized, four molecules (compounds 23, 26, 43, and 59) showed moderate to low inhibition of HIV-1 integrase for 3′-processing and 3′- strand transfer activities. Nonetheless, these compounds possess structural features not seen in known HIV-1 integrase inhibitors and thus can serve as excellent leads for further optimization of anti-HIV-1 integrase activity.

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.

Process for producing 3-anilino-5-pyrazolones

A process for producing a 3-anilino-5-pyrazolone which comprises reacting a β-anilino-β-alkoxy-acrylate with a hydrazine in the presence of a compound having a pKa of about 8 up to about 14.