531-52-2

Basic information

• Product Name: Triphenylformazan
• Synonyms: Triphenylformazan Nitrogen;1,3,5-Triphenylformazane;Triphenylformazane;Diazene, phenylphenyl(phenylhydrazono)methyl-;N'-(Phenylamino)-N-phenyliminobenzenecarboximidamide;1,3,5-Triphenyl-1,2,4,5-tetraaza-1,3-pentadiene;DTTC Formazan;Phenyl(2-phenylhydrazono)(phenylazo)methane
• CAS NO: 531-52-2
• Molecular Formula: C₁₉H₁₆N₄
• Molecular Weight: 300.36
• EINECS: 208-509-1
• Product Categories: Formazans;Tetrazolium Salts & Formazans;marker
• Mol File: 531-52-2.mol
• Article Data: 18

Chemical Properties

• Melting Point: 169-170 °C
• Boiling Point: 431.59°C (rough estimate)
• Flash Point: 221.8 °C
• Appearance: /
• Density: 1.1454 (rough estimate)
• Vapor Pressure: 4.73E-08mmHg at 25°C
• Refractive Index: 1.6140 (estimate)
• Storage Temp.: Store at 2-8
• Solubility: dioxane: 50 mg/mL, clear
• PKA: 11.56±0.10(Predicted)
• Water Solubility: dioxane: 50 mg/mL, clear
• BRN: 753057
• CAS DataBase Reference: Triphenylformazan(CAS DataBase Reference)
• NIST Chemistry Reference: Triphenylformazan(531-52-2)
• EPA Substance Registry System: Triphenylformazan(531-52-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61-24/25-22
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 531-52-2(Hazardous Substances Data)

Usage

Description

Triphenylformazan, also known as 1,3,5-triphenyltetrazolium formazan, is a chemical compound that is widely used in various applications due to its unique properties. It is a red crystalline solid that is soluble in water and has a molecular weight of 287.3 g/mol. Triphenylformazan is known for its ability to form a colored formazan product when reduced, making it a useful indicator in various assays and tests.

Uses

Used in Germination and Viability Tests:
Triphenylformazan is used as an indicator in germination and viability tests to assess the metabolic activity of cells. It is reduced to a colored formazan product, which can be measured spectrophotometrically, providing a quantitative assessment of cell viability and germination potential.
Used in Quantification of TTC Reduction Activity:
In the field of microbiology, Triphenylformazan is used as a standard to study the optical density of formazan produced by 2,3,5-triphenyltetrazolium chloride (TTC)-treated bacterial cells. This allows for the quantification of TTC reduction activity, which is an important parameter in assessing bacterial metabolism and growth.
Used in Seed Testing:
Triphenylformazan is used as a standard in seed testing to evaluate the germination potential of seeds. It is used to study the optical density of formazan produced by TTC-treated milled seeds, providing a quantitative measure of seed viability and germination capacity.
Used in Cardiology Research:
In cardiology research, Triphenylformazan is used to stain heart tissue for infarct size assessment. It can be used in conjunction with perfusion fixation to allow morphometric studies, in addition to histology and immunohistochemistry, providing valuable insights into the extent of tissue damage and the effectiveness of potential treatments.

InChI:InChI=1/C19H16N4/c1-4-10-16(11-5-1)19(22-20-17-12-6-2-7-13-17)23-21-18-14-8-3-9-15-18/h1-15,20H/b22-19-,23-21+

Upstream product

• 64-17-5 ethanol 
• 98-07-7 Benzotrichlorid 
• 100-63-0 phenylhydrazine 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 2684-02-8 benzenediazonium 
• 141-52-6 sodium ethanolate 
• 588-64-7 benzaldehyde phenylhydrazone 
• 100-34-5 benzene diazonium chloride 
• 18039-45-7 2,5-diphenyl-2H-tetrazole 
• 75-91-2 tert.-butylhydroperoxide 
• 99504-94-6 1,3,5-triphenylveradzyl radical 
• 64-19-7 acetic acid 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 4453-80-9 3-nitro-1,5-diphenylformazan 

Downstream Products

• 298-96-4 triphenyltetrazolium chloride 
• 53708-90-0 bis[1,3,5-triphenyl formazanato]nickel(II) 
• 77110-91-9 Os(C₆H₄)N₂C(C₆H₅)N₂C₆H₅(CO)(P(C₆H₅)3)2 
• 53708-90-0 nickel(II) bis[1,3,5-triphenylformazanate] 
• 2154-65-6 1,3,5-triphenylverdazyl 
• 22459-57-0 2,4,6-triphenylverdazyl 
• 1386384-47-9 (E)-ethyl 4-phenyl-1-(phenyldiazenyl)isoquinoline-3-carboxylate 
• 1386384-41-3 (E)-dimethyl 1-(phenyldiazenyl)isoquinoline-3,4-dicarboxylate 
• 1386384-46-8 (E)-di-tert-butyl 1-(phenyldiazenyl)isoquinoline-3,4-dicarboxylate 
• 77123-39-8 Ru(C₆H₄)N₂C(C₆H₅)N₂C₆H₅(CO)(P(C₆H₅)3)2 
• 77110-90-8 Ru(C₆H₄)N₂C(C₆H₅)N₂C₆H₅(CO)(As(C₆H₅)3)2 
• 54387-51-8 bis(1.3.5-triphenyl-formazane)-cobalt(II) 
• 53708-91-1 bis(1,3,5-triphenyl-5-formazanyl)copper 
• 113223-42-0 2,3,5-triphenyl-tetrazolium; acetate 

Relevant articles and documents

Electron spin resonance signals of tetrazolium compounds.

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Synthesis and Electrochemical Properties of 2-(4-R1-Phenyl)-6-(4-R2-phenyl)-4-phenyl-3,4-dihydro1,2,4,5-tetrazin-1(2H)-yls

Abstract: A new methodology for creating electroactive components for organic batteries,based on the construction of a molecular platform including stable3,4-dihydro-1,2,4,5-tetrazin-1(2H)-ylradicals was described. A series of2-(4-R1-phenyl)-6-(4-R2-phenyl)-4-phenyl-3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yls with substituents of various nature wasobtained. It was shown that the substituents R1 inthe aromatic ring at position 2 of the tetrazinyl fragment influence the valueof the oxidation potential in the radical, but do not influence the value of thereduction potentials, while the substituent R2 of thearomatic ring at position 6 influence the values of the reduction potentials andpractically do not influence oxidation potential values. Based on the obtainedelectrochemical data, a correlation structure–potential value was revealed forthe cathodic and anodic process, with the help of which triarylsubstituted3,4-dihydro-1,2,4,5-tetrazin-1(2H)-ylradicals with high values of the electrochemical gap were obtained.

Chromogenic Reaction of 1,1-Dimethylhydrazine with Aryltetrazolium Salts

The reactions of 1,1-dimethylhydrazine with 2,3,5-triphenyl-2Н-tetrazolium and 2,5-diphenyl-3-(4-nitrophenyl)-2Н-tetrazolium chlorides in a solution and on a cellulose carrier have been studied by means of spectrophotometry and chromato–mass spectrometry to develop new chromogenic indicators for detection of 1,1-dimethylhydrazine. 1,3,5-Triphenylformazan and 1,3-diphenyl-5-(4-nitrophenyl)formazan are formed in these reactions, respectively; deep red shifts have been observed. Other products of these reactions result from oligomerization and addition of short-living 1,1-dimethylhydrazyl and tetrazolium radicals.

Microwave mediated solvent free synthesis of formazans catalyzed by simple ionic liquids derived from dialkylammonium salts

A microwave mediated, ionic liquid catalyzed, VOC free and one pot synthesis of formazans was developed. In an alternative procedure, resin immobilized diazonium ions was used as a solid supported reaction for formazan synthesis. The efficiency of both the procedures was examined with respect to yield of product, reduction of reaction time and environmental impact. Products were obtained in a short reaction time and in moderate to high yield. This study was undertaken to find an alternative green protocol for the synthesis of formazans using ionic liquid as catalyst in aqueous media in the absence of corrosive mineral acids, buffered solutions and VOCs.