3656-04-0

Basic information

• Product Name: 1H-Pyrazole-3,5-diamine, 4-[(4-chlorophenyl)azo]-
• CAS NO: 3656-04-0
• Molecular Formula: C9H9ClN6
• Molecular Weight: 236.664
• Mol File: 3656-04-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazole-3,5-diamine, 4-[(4-chlorophenyl)azo]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-3,5-diamine, 4-[(4-chlorophenyl)azo]-(3656-04-0)
• EPA Substance Registry System: 1H-Pyrazole-3,5-diamine, 4-[(4-chlorophenyl)azo]-(3656-04-0)

Safety Data

• Hazardous Substances Data: 3656-04-0(Hazardous Substances Data)

Usage

Physical state

Bright orange, crystalline substance

Uses

pH indicator with a transition range of 3.2 4.4, detecting copper and zinc ions in solutions, potential applications in medicine and cancer research

Azo group

Allows for intense absorption in the visible region, useful for colorimetric assays and tests

Molecular structure

Contains a pyrazole ring with two amino groups (-NH2) at the 3 and 5 positions, an azo group (-N=N-) connecting a 4-chlorophenyl group to the pyrazole ring.

Upstream product

• 106-47-8 4-chloro-aniline 
• 109-77-3 malononitrile 
• 302-01-2 hydrazine 
• 946-76-9 2-[(4-chlorophenyl)hydrazono]malononitrile 
• 882-32-6 p-chlorophenylazomalononitrile 

Downstream Products

• 114275-67-1 2-Amino-3-(4-chloro-phenylazo)-5-methyl-pyrazolo[1,5-a]pyrimidin-7-ol 
• 134045-63-9 3-(4-Chloro-phenylazo)-5,7-diphenyl-pyrazolo[1,5-a]pyrimidin-2-ylamine 
• 1208978-03-3 2-(2',7'-diamino-6'-cyano-3'-(4-chlorophenyldiazenyl)-4'H-spiro(cyclohexa[2,5]diene-1,5'-pyrazolo[1,5-a]pyrimidine)-4-ylidene)malononitrile 
• 1415354-21-0 ((8-(4-chlorophenyl)-diazenyl)-4,5-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)dipyrazolo(1,5-a:3',4'-d)pyrimidin-7-amine 
• 155375-42-1 2,5-diamino-3-((4-chlorophenyl)diazenyl)-7-(methylthio)pyrazolo[1,5-a]pyrimidine-6-carbonitrile 

Relevant articles and documents

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.

Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents

Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.

Synthesis, structure characterization and antimicrobial evaluation of 4-(substituted phenylazo)-3,5-diacetamido-1H-pyrazoles

The present article deals with the synthesis, spectral characterization and antimicrobial activity of phenylazo dyes. All of the synthesized phenylazo dyes were characterized using ATR-FTIR, FT-Raman, 1H NMR, 13C NMR, elemental analy