298-96-4

Basic information

• Product Name: 2,3,5-Triphenyltetrazolium chloride
• Synonyms: 2,3,5-TriphenyltetrazoliuM chloride SynonyMs 2,3,5-Triphenyl-2H-tetrazoliuM chloride;TTC,TTZ,Tetrazolium Red;FLJ37239;LGMD2K;10 MG ABTS TABLETS;BCIP P-TOLUIDINE SALT ULTRA PURE GRADE;TSA PENASE CONTACT 55MM TRIPLE-WRAP;red tetazolium
• CAS NO: 298-96-4
• Molecular Formula: C₁₉H₁₅N₄*Cl
• Molecular Weight: 334.8
• EINECS: 206-071-6
• Product Categories: substrate;Tetrazolium Salts;Tetrazolium Salts & Formazans;Tetrazolium salt
• Mol File: 298-96-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 250 °C(lit.)
• Boiling Point: 490.96°C (rough estimate)
• Flash Point: 91.7oC
• Appearance: faint yellow/
• Density: 1.1704 (rough estimate)
• Vapor Pressure: 0.0615mmHg at 25°C
• Refractive Index: 1.6110 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: may be clear to slightly hazy
• Water Solubility: Soluble in water, ethanol and acetone. Insoluble in ether.
• Sensitive: Light Sensitive & Hygroscopic
• Stability: Stable. Light sensitive. Protect from moisture. Incompatible with strong oxidizing agents.
• Merck: 14,9744
• BRN: 3923356
• CAS DataBase Reference: 2,3,5-Triphenyltetrazolium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-Triphenyltetrazolium chloride(298-96-4)
• EPA Substance Registry System: 2,3,5-Triphenyltetrazolium chloride(298-96-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: XF8100000
• F: 3-8-10
• TSCA: Yes
• Hazardous Substances Data: 298-96-4(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 298-96-4 differently. You can refer to the following data:
1. 2,3,5-Triphenyl-2H-tetrazolium chloride is used as a dye in cell biological studies.
2. 2,3,5-Triphenyltetrazolium chloride is a selective serotonin 5-HT4 receptor agonist and 5-HT3 gastrointestinal prokinetic agent for functional dyspepsia
3. In analytical chemistry as a sensitive reagent for reducing sugars, and to distinguish between a-ketols and simple aldehydes. For staining plant and animal tissue. Germination indicator in testing the ability of seeds to germinate: G. Lakon, Ber. Dtsch. Bot. Ges. 60, 299, 434 (1942). In histochemical studies. In determination of antibiotics; of dehydrogenases.

Definition

ChEBI: An organic chloride salt having 2,3,5-triphenyltetrazolium as the counterion.

General Description

2,3,5-Triphenyltetrazolium chloride is a colorless water-soluble dye. In the mitochondria of living cells, it is reduced to a deep red, water-insoluble compound (formazan). 2,3,5-Triphenyltetrazolium chloride helps to distinguish between viable and infarcted brain tissue after stroke.

Purification Methods

Crystallise TTZ from EtOH or CHCl3, and dry it at 105o. [Beilstein 26 H 363, 26 II 216, 26 III/IV 1774.]

Synthetic route

1,3,5-triphenylformazan (531-52-2) → triphenyltetrazolium chloride (298-96-4)

Conditions	Yield
With thallium(III) acetate In acetic acid	95%
With sodium hydroxide; chlorine In ethanol at -5 - -1℃; for 0.666667h;	92%
With N-chloro-succinimide In dichloromethane; water at 0℃; for 5h;	90%

1,3,5-triphenylformazan (49624-20-6) → triphenyltetrazolium chloride (298-96-4)

Conditions	Yield
With N-chlorobenzotriazole In benzene for 0.25h; Heating;	88%
With hydrogenchloride; isopentyl nitrite In chloroform	40%

N-chloro-succinimide (128-09-6) + 1,3,5-triphenylformazan (531-52-2) → triphenyltetrazolium chloride (298-96-4)

Conditions	Yield
With ethyl acetate

N-chlorophthalimide (3481-09-2) + 1,3,5-triphenylformazan (531-52-2) → triphenyltetrazolium chloride (298-96-4)

Conditions	Yield
With ethyl acetate

tert-butylhypochlorite (507-40-4) + 1,3,5-triphenylformazan (531-52-2) → triphenyltetrazolium chloride (298-96-4)

Conditions	Yield
With potassium hydroxide; chloroform

triphenyltetrazolium borate → triphenyltetrazolium chloride (298-96-4)

Conditions	Yield
With hydrogenchloride	1.7 g

hydrogenchloride (7647-01-0) + 1,3,5-triphenylformazan (531-52-2) + isopentyl nitrite (110-46-3) → triphenyltetrazolium chloride (298-96-4)

benzaldehyde (100-52-7) + aniline (62-53-3) + phenylhydrazine (100-63-0) → triphenyltetrazolium chloride (298-96-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium nitrite / water / 2 h / 20 °C 2: N-chloro-succinimide / water; dichloromethane / 5 h / 0 °C View Scheme

Upstream product

• 128-09-6 N-chloro-succinimide 
• 531-52-2 1,3,5-triphenylformazan 
• 7647-01-0 hydrogenchloride 
• 110-46-3 isopentyl nitrite 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 100-63-0 phenylhydrazine 
• 49624-20-6 1,3,5-triphenylformazan 
• 507-40-4 tert-butylhypochlorite 
• 3481-09-2 N-chlorophthalimide 

Downstream Products

• 6130-87-6 Tetramethyltetrazon 
• 531-52-2 1,3,5-triphenylformazan 
• 1258500-10-5 2,3,5-triphenyltetrazolium hexachlorophosphate 
• 1025-89-4 5‐methyl‐1,3‐diphenyl‐1H‐1,2,4‐triazole 
• 49624-20-6 1,3,5-triphenylformazan 
• 116997-37-6 1-phenyl-3-hydroxy-1,2-propanedione 
• 588-64-7 benzaldehyde phenylhydrazone 
• 1063-72-5 2,3,5-triphenyltetrazolium picrate 
• 236-27-1 2,3-diphenyltetrazolium ion 
• 902-00-1 2,3,5-triphenyltetrazolinyl 
• 46721-85-1 N′-phenylbenzimidohydrazide 

Relevant articles and documents

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Method for preparing chlorinated-3-substituted-2,5-diphenyl tetrazole under catalysis of copper Lewis acid surfactant

The invention belongs to the technical field of organic synthesis and specifically relates to a method for preparing chlorinated-3-substituted-2,5-diphenyl tetrazole under the catalysis of a copper Lewis acid surfactant. The method comprises the following steps: 1) reacting benzaldehyde, phenylhydrazine, arylamine and sodium nitrite in solvent water by taking a copper Lewis acid surfactant Cu(OSO2CnH2n+1)2 as a catalyst to obtain 3-aryl-2,5-diphenylformazan; and 2) cyclizing and chlorinating 3-aryl-2,5-diphenylformazan in a mixed solvent of dichloromethane and water under the condition of a solid chlorination reagent N-chlorosuccinimide to obtain chlorinated-3-substituted-2,5-diphenyl tetrazole. By using the method, three-step conversion is completed according to a ''one-pot method'' continuous strategy, not only is an intermediate separation step omitted, but also the purification step is simple as well as convenient and easy to operate.

Imidazole compounds

A novel class of imidazo heterocyclic compounds, pharmaceutical compositions comprising them and use thereof in the treatment and/or prevention of diseases and disorders related to the histamine H3 receptor. More particularly, the compounds are useful for the treatment and/or prevention of diseases and disorders in which an interaction with the histamine H3 receptor is beneficial.

1-Chlorobenzotriazole-Mediated Ring Closure of 1,3,5-Triarylformazans: Improved Syntheses of 2,3,5-Triaryl-2H-tetrazolium Salts

Oxidative ring closure of mono- and bis-triarylformazans mediated by easily available 1-chlorobenzotriazole leads to the corresponding 2,3,5-triaryl-2H-tetrazolium chlorides in yields of 70-97percent.