7014-08-6

Usage

Physical appearance

Yellow to orange crystalline powder

Solubility

Sparingly soluble in water

Uses

Dye intermediate, synthesis of other organic compounds, potential precursor for azo dyes

Applications

Textile industry, development of new materials and pharmaceuticals

Handling precautions

Consideration of potential health and environmental impacts required

Upstream product

• 1448-98-2 N-(aminocarbonyl)-2-cyano-acetamide 
• 100-34-5 benzene diazonium chloride 
• 372-09-8 cyanoacetic acid 
• 105-56-6 ethyl 2-cyanoacetate 
• 2118-44-7 5-cyano-2,3-diphenyl-2H-tetrazolium chloride 
• 37463-94-8 bis-(cyanomethyl)-sulfone 
• 62-53-3 aniline 
• 65157-84-8 β-piperidinoacrylonitrile 
• 142-04-1 aniline hydrochloride 
• 2684-02-8 benzenediazonium 
• 87613-42-1 α-Cyano-α-phenylhydrazono-o-carboxacetanilide 

Downstream Products

• 1967-52-8 1,5-diphenylformazan-3-carboxylic acid 
• 53543-28-5 4,5-diamino-2-phenyl-{1,2,3}triazole 
• 28794-80-1 4-amino-5-phenylazo-2-phenyl-1,2,3-triazole 
• 152574-45-3 4-acetamido-5-phenylazo-2-phenyl-1,2,3-triazole 
• 28794-80-1 2-phenyl-5-phenylazo-2H-[1,2,3]triazol-4-yl-amine 
• 2118-44-7 5-cyano-2,3-diphenyl-2H-tetrazolium chloride 
• 28716-51-0 2-phenylazo-2-phenylhydrazonoacetamide oxime 

Relevant academic research and scientific papers

Synthesis and spectral properties of symmetrical and asymmetrical 3-Cyano-1,5-diarylformazan dyestuffs for dyeing polyester fabrics

IN THIS study, we report on a general synthetic approach to both symmetrical and asymmetrical 3-cyano-1,5-diarylformazan dyes. The reaction of enaminonitrile with aromatic diazonium salts in slightly acidic medium affords arylhydrazonals as stable intermediate that are readily converted into asymmetrical formazans via second azo-coupling in a weak alkaline medium. Symmetrical formazan dyestuffs are synthesized directly via double azo-coupling of the key intermediate 3-piperidinylacrylonitrile with the corresponding diazonium salts in weak alkaline medium using sodium acetate as a weak base. The structures of the prepared dyestuffs and intermediates are demonstrated by elemental analysis (C, H, N),1H and13C NMR, FTIR and GC-MS spectroscopic techniques. The prepared formazan disperse colorants are applied to dye polyester fabric to give satisfactory fastness properties to wash, perspiration, rubbing and light.

Microwave-Assisted Synthesis of Arylazoaminopyrazoles as Disperse Dyes for Textile Printing

The synthesis of heterocyclic azo-dyes via conventional heating and microwave (MW) heating was investigated. From a sequence of reactions starting from cyanoacetic acid, 4-arylazo-2H-pyrazol-3-ylamines and 4-arylazo-2-phenyl-2H-pyrazol-3-ylamines were obtained. The structures these compounds were obtained by inspection of spectroscopic and analytical techniques including1H and13C NMR spectroscopy, IR spectroscopy, mass spectrometry, and elemental analysis. The fastness properties and UV/Vis absorption spectroscopic data of these disperse dyes in printing polyester fabrics were investigated.

Syntheses of formazans under phase-transfer conditions

Several 1,3,5-triarylformazans were synthesized (42-77%) using a new methodology. Azo-coupling of aryldiazonium salts with arylaldehyde arylhydrazones under mild basic conditions in two-phase liquid-liquid media is efficiently promoted by phase-transfer catalysts (onium salts or dicyclohexano-18-crown-6) at 5-25°C. The condensation of benzaldehyde with phenylhydrazine followed by phase-transfer catalyzed azo-coupling with phenyldiazonium chloride (one-pot procedure) gave 1,3,5-triphenylformazan in a 54% yield without isolation of the intermediate benzaldehyde phenylhydrazone. A double azo-coupling reaction of phenyldiazonium chloride with 9 different CH-active compounds afforded corresponding formazan only in the case of phenylpyruvic acid. Reaction in malonamide gave 3-carbamoyl-1,5-diphenylformazan instead of the expected 1,5-diphenylformazan.

Structural Studies on 3-Acetyl-1,5-Diaryl and 3-Cyano-1,5-Diaryl Formazan Chelates with Cerium(III), Thorium(IV) and Uranium(VI)

Solid complexes of 3-acetyl-1,5-diaryl and 3-cyano-1,5-diaryl formazans were prepared and characterized by elemental analysis, IR, NMR, TGA and DTA analyses.Based on these studies, the suggested general formula for the complexes is -)n or (NO3- or Cl-)x*(H2O)y or (C2H5OH or DMSO)z, where HL = formazan M = Ce3+, Th4+, and UO22+, m = 1-2, n = 0-3, x = 0-3, y = 0-4 and z = 0-3.The metal ions are expected to have coordination numbers 6-8. - Keywords: Complexes of 3-acetyl and 3-cyano formazans; Ce(III); Th(IV); U(VI)

Activated Nitriles in Heterocyclic Synthesis: Reaction of Ethyl Cyanoacetate with Anthranilic Acid

Ethyl cyanoacetate (I) reacts with anthranilic acid (II) in refluxing aq. pyridine to yield 2-carboxycyanoanilide (III), while refluxing in dry pyridine a mixture of 3-cyano-2-hydroxyquinolin-4-one (IV) and 12H-6-carboxamido-5,7-dihydroquinoquinazoline (V) is obtained.III on treatment with aryldiazonium salts furnishes the hydrazones (VI) or formazan (VII) depending upon the amount of the salts used.III on coupling with 3-methyl-4-phenylpyrazol-5-diazonium chloride (VIII) furnishes 7-amino-6-(o-carboxamido)2-methyl-3-phenylpyrazolo-as-triazine (IX).III also reacts with thioglycollic acid to afford thiazolin-4-one derivative (XI), while with aromatic aldehydes the arylidene derivatives (XIIa-c) are obtained.