ChemicalBook Product Catalog Analytical Chemistry Analysis reagents General Analytical Reagents 2,3,5-Triphenyltetrazolium chloride

2,3,5-Triphenyltetrazolium chloride

Product Name2,3,5-Triphenyltetrazolium chloride
CAS298-96-4
MFC19H15ClN4
MW334.8
EINECS206-071-6
MOL File298-96-4.mol

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.
Major Application	diagnostic assay manufacturing hematology histology
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
InChI	1S/C19H15N4.ClH/c1-4-10-16(11-5-1)19-20-22(17-12-6-2-7-13-17)23(21-19)18-14-8-3-9-15-18;/h1-15H;1H/q+1;/p-1
InChIKey	PKDBCJSWQUOKDO-UHFFFAOYSA-M
SMILES	[Cl-].c1ccc(cc1)-c2nn(-c3ccccc3)[n+](n2)-c4ccccc4
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	TSCA listed
HS Code	29339900
Storage Class	4.1B - Flammable solid hazardous materials
Hazard Classifications	Eye Irrit. 2 Flam. Sol. 1 Skin Irrit. 2
Toxicity	LD50 intravenous in mouse: 5600ug/kg

MSDS

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

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

531-52-2

298-96-4

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

2,3,5-Triphenyltetrazolium chloride

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