2,3,5-Triphenyltetrazolium chloride Chemical Properties

Melting point:

250 °C(lit.)

Boiling point:

490.96°C (rough estimate)

Density 

1.1704 (rough estimate)

bulk density

230kg/m3

refractive index 

1.6110 (estimate)

storage temp. 

2-8°C

solubility 

H₂O: may be clear to slightly hazy

form 

powder

color 

faint yellow

PH

3.7 (20°C, 10g/L in H2O)

Water Solubility 

Soluble in water, ethanol and acetone. Insoluble in ether.

λmax

247 nm

Sensitive 

Light Sensitive & Hygroscopic

Merck 

14,9744

BRN 

3923356

Stability:

Stable. Light sensitive. Protect from moisture. Incompatible with strong oxidizing agents.

Biological Applications

Algae viability assay; microbial growth assays; transketolase activity screening assays; detecting bacteria,g-hydroxybutyric acid (GHB),microorganisms,myocardial infarction; measuring dehydrogenase activity; treating cancer

InChIKey

PKDBCJSWQUOKDO-UHFFFAOYSA-M

CAS DataBase Reference

298-96-4(CAS DataBase Reference)

EPA Substance Registry System

2,3,5-Triphenyltetrazolium chloride (298-96-4)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36

WGK Germany 

3

RTECS 

XF8100000

F 

3-8-10

TSCA 

Yes

HS Code 

29339900

Toxicity

LD50 intravenous in mouse: 5600ug/kg

MSDS

• Language:English Provider:2,3,5-Triphenyl-2H-tetrazolium chloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,3,5-Triphenyltetrazolium chloride Usage And Synthesis

Chemical Properties

white powder

Uses

2,3,5-Triphenyl-2H-tetrazolium chloride is used as a dye in cell biological studies.

Uses

2,3,5-Triphenyltetrazolium chloride is a selective serotonin 5-HT4 receptor agonist and 5-HT3 gastrointestinal prokinetic agent for functional dyspepsia

Uses

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.

Synthesis

E. The 2,3,5-triphenylformamidine (IV-1) solid obtained in Step D was mixed with 300 mL of dichloromethane and 300 mL of water. After the solid was completely dissolved, N-chlorosuccinimide (0.11 mol, 14.7 g) was added and the reaction was carried out with stirring at 0 °C for 5 h. F. The reaction mixture from Step E was allowed to partition and the upper aqueous phase was separated. The organic phase was distilled under reduced pressure to remove the solvent to give the crude product 2,3,5-triphenyltetrazole (V-1). The crude product was purified by recrystallization with chloroform to give 30.2 g of pure product (yield: 90%).

Purification Methods

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

References

[1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983, vol. 22, # 8, p. 771 - 775
[2] J. Appl. Chem. USSR (Engl. Transl.), 1983, vol. 56, # 3, p. 617 - 621
[3] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1983, vol. 56, # 3, p. 649 - 653
[4] Patent: CN108440433, 2018, A. Location in patent: Paragraph 0057; 0058; 0059; 0064; 0065
[5] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 5, p. 404 - 406

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