146-68-9

Basic information

• Product Name: 2-(4-Iodophenyl)-3-(4-nitrophenyl)-5-phenyltetrazolium chloride
• Synonyms: 3-(4-iodophenyl)-2-(4-nitrophenyl)-5-phenyl-2H-tetrazol-3-iuM chloride;IodonitrotetrazoliuM chloride (INT);IodonitrotrtrazoliuM chloride;Iodonitrotetrazolium chloride 95%;Iodonitrotetrazolium chloride Vetec(TM) reagent grade, >=98%;Iodonitrotetrazolium chloride Vetec(TM) reagent grade, 95%;INT Iodonitrotetrazolium chloride;IODONITROTETRAZOLIUM
• CAS NO: 146-68-9
• Molecular Formula: C₁₉H₁₃IN₅O₂*Cl
• Molecular Weight: 505.7
• EINECS: 205-676-2
• Product Categories: Heterocyclic Building Blocks;Tetrazoles;marker;Tetrazolium Salts;Tetrazolium Salts & Formazans;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Tetrazolium salt
• Mol File: 146-68-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 240 °C (dec.)(lit.)
• Boiling Point: 567.5 °C at 760 mmHg
• Flash Point: 297 °C
• Appearance: White to off-white/Powder, Crystals and/or Chunks
• Vapor Pressure: 6.76E-13mmHg at 25°C
• Storage Temp.: Store at 2-8
• Solubility: methanol: water (1:1): 50 mg/mL hot, very faintly turbid, v
• Water Solubility: soluble
• Sensitive: Light Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 4093224
• CAS DataBase Reference: 2-(4-Iodophenyl)-3-(4-nitrophenyl)-5-phenyltetrazolium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Iodophenyl)-3-(4-nitrophenyl)-5-phenyltetrazolium chloride(146-68-9)
• EPA Substance Registry System: 2-(4-Iodophenyl)-3-(4-nitrophenyl)-5-phenyltetrazolium chloride(146-68-9)

Safety Data

• Hazard Codes: Xn,F,Xi
• Statements: 20/21/22-68/20/21/22-36/37/38-11
• Safety Statements: 36/37-36/37/39-26-22-16
• RIDADR: 2811
• WGK Germany: 3
• F: 3-8-10
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 146-68-9(Hazardous Substances Data)

Usage

Description

2-(4-Iodophenyl)-3-(4-nitrophenyl)-5-phenyltetrazolium chloride, also known as Iodonitrotetrazolium (INT) chloride, is a monotetrazolium salt used as an indicator dye. It is reduced to an insoluble formazan that is used as a vital dye or indicator of cellular redox activity. Reduction commonly results from the activity of dehydrogenases, although non-enzymatic electron transfer reactions can occur in the presence of an intermediate electron acceptor. INT is commonly used to measure the respiratory activity of microorganisms in a variety of contexts. It is a slightly yellow powder.

Uses

1. Used in Enzyme Assays:
2-(4-Iodophenyl)-3-(4-nitrophenyl)-5-phenyltetrazolium chloride is used as an electron acceptor for the colorimetric assay of various dehydrogenases. The reduction of INT to iodonitrotetrazolium formazan, a water-insoluble violet-colored dye, allows for the measurement of dehydrogenase activity in different applications.
2. Used in Cell Staining:
Iodonitrotetrazolium chloride has been used for the staining of cells, providing a visual indication of cellular redox activity. This staining process can be useful in various research and diagnostic applications.
3. Used in Enzymatic Assays of D-arabinitol:
2-(4-Iodophenyl)-3-(4-nitrophenyl)-5-phenyltetrazolium chloride is used as a coupling agent in the enzymatic assay of D-arabinitol, a sugar alcohol that plays a role in certain metabolic processes.
4. Used in Microorganism Respiratory Activity Measurement:
Iodonitrotetrazolium chloride is used to measure the respiratory activity of microorganisms in various contexts, such as environmental monitoring, bioremediation, and microbial ecology studies.

Purification Methods

Recrystallise the chloride from H2O, aqueous EtOH or EtOH/Et2O. Alternatively, dissolve it in the minimum volume of EtOH and add Et2O; or dissolve it in hot H2O (charcoal), filter and precipitate it by adding conc HCl. Filter the solid off and dry it at 100o. Its solubility in H2O at 25o is 0.5%, and in hot MeOH/H2O (1:1) it is 5%. [Fox & Atkinson J Am Chem Soc 72 3629 1950, Beilstein 26 III/IV 1776.]

InChI:InChI=1/C19H14IN5O2.ClH/c20-15-6-8-16(9-7-15)23-21-19(14-4-2-1-3-5-14)22-24(23)17-10-12-18(13-11-17)25(26)27;/h1-13H,(H,21,22);1H

Synthetic route

n-Butyl nitrite (544-16-1) + INT-formazan (136196-46-8) → 2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-3H-tetrazol-2-ium chloride (146-68-9)

Conditions	Yield
With hydrogenchloride; ethanol

2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-3H-tetrazol-2-ium chloride (146-68-9) → INT-formazan (136196-46-8)

Conditions	Yield
In water Kinetics; Reduction; Microbiological reaction;

sodium molybdate dihydrate (7631-95-0) + 1,2-dihydroxy-4-nitrobenzene (3316-09-4) + 2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-3H-tetrazol-2-ium chloride (146-68-9) → [2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-2H-tetrazolium][MoO2(4-nitrocatechol(-2H))2]

Conditions	Yield
In water mixing of aq. solns. of Na2MoO4*2H2O, 4-nitrocatechol and 2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-2H-tetrazolium chloride in acidic medium (pH 2.8 - 4.0); pptn., filtration, washing with cold water, drying at 75-80°C;

2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-3H-tetrazol-2-ium chloride (146-68-9) → INT-formazan (7781-49-9)

Conditions	Yield
With Gerovital H3; xanthine oxidase; xanthin at 25℃; for 0.166667h; pH=7.4; aq. phosphate buffer; Enzymatic reaction;
With potassium superoxide; C11H15CuNO5 In dimethyl sulfoxide pH=7.1; borate buffer;

iron(III) ammonium sulfate dodecahydrate + 1,2-dihydroxy-4-nitrobenzene (3316-09-4) + 2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-3H-tetrazol-2-ium chloride (146-68-9) → Fe(3+)*3C6H3NO4(2-)*3C19H13IN5O2(1+)

Conditions	Yield
With sulfuric acid In water

Upstream product

• 544-16-1 n-Butyl nitrite 
• 136196-46-8 INT-formazan 

Downstream Products

• 136196-46-8 INT-formazan 
• 7781-49-9 INT-formazan 

Relevant articles and documents

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