3722-12-1

Basic information

• Product Name: [2-(4-nitrophenyl)hydrazinylidene]propanedinitrile
• Synonyms: [(4-Nitrophenyl)hydrazono]malononitrile; Propanedinitrile, 2-[2-(4-nitrophenyl)hydrazinylidene]-
• CAS NO: 3722-12-1
• Molecular Formula: C₉H₅N₅O₂
• Molecular Weight: 215.1683
• Mol File: 3722-12-1.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 382.5°C at 760 mmHg
• Flash Point: 185.1°C
• Density: 1.36g/cm³
• Vapor Pressure: 4.7E-06mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: [2-(4-nitrophenyl)hydrazinylidene]propanedinitrile(CAS DataBase Reference)
• NIST Chemistry Reference: [2-(4-nitrophenyl)hydrazinylidene]propanedinitrile(3722-12-1)
• EPA Substance Registry System: [2-(4-nitrophenyl)hydrazinylidene]propanedinitrile(3722-12-1)

Safety Data

• Hazardous Substances Data: 3722-12-1(Hazardous Substances Data)

Usage

General Description

[2-(4-nitrophenyl)hydrazinylidene]propanedinitrile is a chemical compound with the molecular formula C9H6N6O2. It is a hydrazine derivative with a dinitrile group, which gives it potential applications in organic synthesis and pharmaceutical research. The compound contains a nitro group and a phenyl ring, which can influence its chemical reactivity and properties. It is important to handle this compound with caution due to its potential hazardous properties. Research on [2-(4-nitrophenyl)hydrazinylidene]propanedinitrile is ongoing to explore its potential applications and properties.

Upstream product

• 922-64-5 1,1-dicyanoethylene 
• 100-01-6 4-nitro-aniline 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 109-77-3 malononitrile 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 87113-87-9 5-(4-Nitro-phenylazo)-cyclopenta-1,3-diene-1,2,3,4,5-pentacarboxylic acid pentamethyl ester 
• 101225-70-1 (p-nitrophenyl)azo-tert-cumylmalonitrile 
• 127702-38-9 (2-(4-nitrophenylhydrazono)-3-iminopropanedinitrile)-S-thioacetic acid 
• 67-56-1 methanol 

Downstream Products

• 62679-04-3 4-((4-nitrophenyl)diazenyl)-1H-pyrazole-3,5-diamine 
• 1149376-81-7 4-nitrophenylhydrazono-1H-tetrazol-5-yl-acetonitrile 
• 451454-51-6 Ag(4-nitrophenylhydrazonatepropanedinitrile) 
• 134426-12-3 4-amino-2,6-dioxo-5-(p-nitrophenylhydrazono)-1,2,5,6-tetrahydropyrid-3-yl-pyridiniumchlorid 
• 134425-95-9 2-(4-nitrophenyl)-4-cyano-5-morpholino-1-yl-2H-[1,2,3]triazole 
• 134426-09-8 2-(p-nitrophenylhydrazono)-2-cyan-N-chloracetyl-acetamid 

Relevant articles and documents

A combined experimental and DFT investigation of disazo dye having pyrazole skeleton

Disazo dye containing pyrazole skeleton has been synthesized. The structure of the dye has been confirmed by using FT-IR, 1H NMR, 13C NMR, HRMS spectral technique and elemental analysis. The molecular geometry and infrared spectrum are also calculated by the Density Functional Theory (DFT) employing B3LYP level with 6-311G (d,p) basis set. The chemical shifts calculation for 1H NMR of the title molecule is done by using by Gauge-Invariant Atomic Orbital (GIAO) method by utilizing the same basis sets. The total density of state, the partial density of state and the overlap population density of state diagram analysis are done via Gauss Sum 3.0 program. Frontier molecular orbitals such as highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and molecular electrostatic potential surface on the title molecule are predicted for various intramolecular interactions that are responsible for the stabilization of the molecule. The experimental results and theoretical values have been compared.

Effect of new carbonyl cyanide aromatic hydrazones on biofilm inhibition against methicillin resistant: Staphylococcus aureus

Carbonyl cyanide m-chlorophenylhydrazone (CCCP), as a protonophore, in combination with antibiotics exhibited potentiating antibacterial activity. To improve CCCP's potency and toxicity, a series of aromatic hydrazones were synthesized and their antimicrobial activity was evaluated; amongst them, compounds 2e and 2j with a strong para-electron-withdrawing substituent (-NO2 and -CF3) at the phenyl ring had the lowest MICs against both S. aureus and methicillin resistant Staphylococcus aureus (1.56 and 1.56 μM, respectively). Some compounds in combination with antibiotics exhibited potentiate Gram-positive antibacterial activity; compound 2e was found to display unaided or synergistic efficacy against MRSA. In particular, when compound 2e is combined with ofloxacin, it has a good synergistic effect against MRSA. Moreover, electron microscopy revealed that compound 2e inhibits biofilm formation and effectively eradicates preformed biofilm. MTT assay showed that compound 2e displays as low toxicity as CCCP. Overall, our data showed that the aromatic hydrazone is a promising scaffold for anti-staphylococcal drug development.

Computer-aided molecular design of pyrazolotriazines targeting glycogen synthase kinase 3

Numerous studies have highlighted the implications of the glycogen synthase kinase 3 (GSK-3) in several processes associated with Alzheimer’s disease (AD). Therefore, GSK-3 has become a crucial therapeutic target for the treatment of this neurodegenerative disorder. Hereby, we report the design and multistep synthesis of ethyl 4-oxo-pyrazolo[4,3-d][1–3]triazine-7-carboxylates and their biological evaluation as GSK-3 inhibitors. Molecular modelling studies allow us to develop this new scaffold optimising the chemical structure. Potential binding mode determination in the enzyme and the analysis of the key features in the catalytic site are also described. Furthermore, the ability of pyrazolotriazinones to cross the blood–brain barrier (BBB) was evaluated by passive diffusion and those who showed great GSK-3 inhibition and permeation to the central nervous system (CNS) showed neuroprotective properties against tau hyperphosphorylation in a cell-based model. These new brain permeable pyrazolotriazinones may be used for key in vivo studies and may be considered as new leads for further optimisation for the treatment of AD.