55653-13-9

Basic information

• Product Name: carbonyl cyanide 2-nitrophenylhydrazone
• Synonyms: carbonyl cyanide 2-nitrophenylhydrazone;2-[(2-nitrophenyl)hydrazinylidene]propanedinitrile
• CAS NO: 55653-13-9
• Molecular Formula: C₉H₅N₅O₂
• Molecular Weight: 215.17
• Mol File: 55653-13-9.mol

Chemical Properties

• Boiling Point: 368.7°C at 760 mmHg
• Flash Point: 176.8°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 1.25E-05mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: carbonyl cyanide 2-nitrophenylhydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: carbonyl cyanide 2-nitrophenylhydrazone(55653-13-9)
• EPA Substance Registry System: carbonyl cyanide 2-nitrophenylhydrazone(55653-13-9)

Safety Data

• Hazardous Substances Data: 55653-13-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H5N5O2/c10-5-7(6-11)12-13-8-3-1-2-4-9(8)14(15)16/h1-4,13H

Upstream product

• 922-64-5 1,1-dicyanoethylene 
• 88-74-4 2-nitro-aniline 
• 109-77-3 malononitrile 
• 119-66-4 2-nitrobenzenediazonium chloride 

Downstream Products

• 3253-29-0 O,O,O,O-tetraisopropyl pyrophosphorotrithioate 
• 1149376-80-6 2-nitrophenylhydrazono-1H-tetrazol-5-yl-acetonitrile 

Relevant articles and documents

Structure and nonlinear optical properties of phenylazo compounds. Structural characterization of 3-amino-3-morpholinyl-2-(o-nitrophenylazo)-propenonitrile and o-nitrophenylhydrazonomalononitrile

The results of synthesis, X-ray and spectral investigations, powder second harmonic generation (SHG), molecular mechanics and quantum chemical calculations of the potential nonlinear optical compound, 3-amino-3-morpholinyl-2-(o-nitrophenylazo)-propenonitr

Novel heterocyclic disazo dyes containing pyrazole and phenylpyrazole. part 1: Synthesis, characterization, solvent polarity and acid-base sensitive characteristics

A series of diazotised aniline and aniline derivative compounds were reacted with solution of malononitrile in pyridine at 0–5 °C were obtained 1a-1m compounds. Then 4-arylazo-3,5-diamino-1H-pyrazole (2a-2m) derivatives were synthesized by coupling arylazo malononitrile compounds with hydrazine. Finally, the synthesized pyrazole derivative 2a-2m compounds were again diazotised. By reacting these diazotised compounds with 3-amino-5?hydroxy-1-phenylpyrazole, the new thirteen heterocyclic disazo dyes (3a-3m) were joined the dye literature and the dye industry. The structures of these newly synthesized compounds were characterized using elemental analysis and spectroscopic methods such as Fourier transform infrared spectroscopy-Attenuated total reflectance (FT-IR-ATR), 1H-Nuclear magnetic resonance (1H NMR) spectroscopy and mass spectroscopy. Then solvatochromic properties and solvent effect in dimethyl sulfoxide, dimethyl formamide, acetonitrile, acetic acid, methanol and chloroform were investigated. In addition, the effects of organic and inorganic acids and bases on the absorption spectra of the compounds and the substituent effect of the phenyl ring-bound groups were investigated.

Discovery, SAR study and ADME properties of methyl 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate as an HIV-1 replication inhibitor

Inspired by the antiviral activity of known pyrazole-based HIV inhibitors, we screened our in-house library of pyrazole-based compounds to evaluate theirin celluloactivity against HIV-1 replication. Two hits with very similar structures appeared from single and multiple-round infection assays to be non-toxic and active in a dose-dependent manner. Chemical expansion of their series allowed an in-depth and consistent structure-activity-relationship study (SAR) to be built. Further ADME evaluation led to the selection of 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate with an advantageous pharmacokinetic profile. Finally, examination of its mode of action revealed that this compound does not belong to the three main classes of anti-HIV drugs, a feature of prime interest in the context of viral resistance.

Microwave-assisted preparation of 4-amino-3-cyano-5-methoxycarbonyl-N-arylpyrazoles as building blocks for the diversity-oriented synthesis of pyrazole-based polycyclic scaffolds

The synthesis of 4-amino-3-cyano-N-arylpyrazoles A based on a Thorpe-Ziegler cyclization as the key step has been achieved using microwave activation. Via a new diversity-oriented synthetic pathway, these highly functionalized building blocks allowed the access to various heteroaromatic scaffolds such as pyrazolo-pyridines B, pyrazolo-pyrimidines C and pyrazolo-oxadiazoles D. Interestingly, these platforms contain three to four reactive sites that could be used for post-functionalization in order to further increase the molecular diversity.

Facile synthesis of 3,5-diaminopyrazole derivatives from nitrile intermediates

A novel series of 3,5-diaminopyrazole derivatives (2a-n) was achieved by the reaction of [2-(4-substitutedphenyl) hydrazinylidene] nitrile (1) with various substituted benz hydrazides. The synthesized compounds were characterized by 1H NMR, IR, mass spectroscopy and elemental analyses. The antioxidant potency of the compounds was tested keeping BHA as standard. Compounds 2a, 2b and 2c showed excellent antioxidant property comparable with the standard employed.

Synthesis and antimicrobial activity studies of some novel substituted phenylhydrazono-1H-tetrazol-5-ylacetonitriles

In this study, some substituted phenylhydrazono-1H-tetrazol-5-yl- acetonitriles have been synthesized (2a-o, 2a and 2k are known compounds). The synthesized compounds were characterized by spectroscopic methods [Fourier-transform infrared (FTIR), nuclear magnetic resonance (NMR), mass spectroscopy (MS)]. In addition, antimicrobial activities of synthesized compounds were investigated against Bacillus cereus RSKK 863, Escherichia coli ATCC 3521, Pseudomonas aeruginosa ATCC 2921, and Staphylococcus aureus TP32. These compounds had antimicrobial effect against these bacteria (except for 21). Birkhaeuser Boston 2009.

4-Arylazo-3,5-diamino-1H-pyrazole CDK inhibitors: SAR study, crystal structure in complex with CDK2, selectivity, and cellular effects

In a routine screening of our small-molecule compound collection we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of ATP antagonists with moderate potency against CDK2-cyclin E. A preliminary SAR study based on 35 analogues suggests ways in which the pharmacophore could be further optimized, for example, via substitutions in the 4-aryl ring. Enzyme kinetics studies with the lead compound and X-ray crystallography of an inhibitor-CDK2 complex demonstrated that its mode of inhibition is competitive. Functional kinase assays confirmed the selectivity toward CDKs, with a preference for CDK9-cyclin T1. The most potent inhibitor, 4-[(3,5-diamino-1H-pyrazol-4-yl) diazenyl]phenol 31b (CAN508), reduced the frequency of S-phase cells of the cancer cell line HT-29 in antiproliferation assays. Further observed cellular effects included decreased phosphorylation of the retinoblastoma protein and the C-terminal domain of RNA polymerase II, inhibition of mRNA synthesis, and induction of the tumor suppressor protein p53, all of which are consistent with inhibition of CDK9.