60-10-6

Basic information

• Product Name: Dithizone
• Synonyms: Dithizone,Diphenylthiocarbazone;DIPHENYLTHIOCARBAZONE, REAG;Dithizone ACS Diphenylthiocarbazone ACS;Dithizone (min. 98%);DITHIZONE FOR ANALYSIS (1,5-DIPHENYLT;N',2-Diphenyldiazenecarbothiohydrazide 98+%;Dithizone ACS reagent, >=85.0%;Dithizone Practical Grade
• CAS NO: 60-10-6
• Molecular Formula: C₁₃H₁₂N₄S
• Molecular Weight: 256.33
• EINECS: 200-454-1
• Product Categories: Chelating Agents & Ligands;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycles
• Mol File: 60-10-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 168°C (dec.)
• Boiling Point: 376.1 °C at 760 mmHg
• Flash Point: 181.2 °C
• Appearance: /Crystalline
• Density: 1.2578 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Store at room temperature.
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: pK1:4.50;pK2:15 (25°C)
• Water Solubility: Soluble in ethanol, chloroform, dimethylsulfoxide, and pyridine. Insoluble in water.
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,3377
• BRN: 748838
• CAS DataBase Reference: Dithizone(CAS DataBase Reference)
• NIST Chemistry Reference: Dithizone(60-10-6)
• EPA Substance Registry System: Dithizone(60-10-6)

Safety Data

• Hazard Codes: Xi
• Statements: 22-36/37/38
• Safety Statements: 36-26
• RIDADR: 2811
• WGK Germany: 3
• RTECS: LQ9450000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 60-10-6(Hazardous Substances Data)

Usage

Description

Dithizone, also known as Diphenylthiocarbazone, is an organosulfur compound that acts as a chelating agent, forming stable complexes with various metals such as zinc, lead, and mercury. It is characterized by its dark brown or black crystalline appearance.

Uses

Used in Chemical Analysis:
Dithizone is used as a sensitive reagent for detecting and estimating minute amounts of heavy metals, including cobalt (Co), copper (Cu), lead (Pb), and mercury (Hg). It is particularly effective as an indicator for trace amounts of lead.
Used in Medical Applications:
In the medical field, Dithizone is utilized to assess the purity of human pancreatic islet preparations, which are crucial for transplantation into patients with type 1 diabetes. This ensures the safety and effectiveness of the transplant procedure.
Used in Heavy Metal Poisoning Treatment:
Dithizone acts as a chelating agent for heavy metal poisoning, helping to remove toxic metals from the body. As a ligand, it forms complexes with metals like zinc, lead, and mercury, facilitating their removal during treatment.
Used in Environmental and Industrial Applications:
Dithizone is employed in the liquid-liquid and solid phase extraction of various metals due to its ability to form stable complexes with these metals. This makes it a valuable tool in environmental monitoring and industrial processes where metal contamination is a concern.
Used as a Titrant:
In addition to its other applications, Dithizone is used as a titrant in the quantitative determination of heavy metals, providing a reliable method for measuring their concentrations in various samples.

Purification Methods

The crude dithizone is dissolved in CCl4 to give a concentrated solution. This is filtered through a sintered glass funnel and shaken with 0.8M aqueous ammonia to extract dithizonate ion. The aqueous layer is washed with several portions of CCl4 to remove undesirable materials. The aqueous layer is acidified with dilute H2SO4 to precipitate pure dithizone. This is dried in a vacuum. When only small amounts of dithizone are required, purification by paper chromatography is convenient. [Cooper & Hibbits J Am Chem Soc 75 5084 1933.] Instead of CCl4, CHCl3 can be used, and the final extract, after washing with water, can be evaporated in air at 40-50o and dried in a desiccator. It complexes with Cd, Hg, Ni and Zn. [Beilstein 16 H 26, 16 IV 18.]

InChI:InChI=1/C13H12N4S/c14-15-13(18)16-17(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,14H,(H,16,18)

Upstream product

• 22027-16-3 phenylhydrazinium-phenyldithiocarbazate 
• 622-03-7 diphenyl thiocarbazide 
• 4453-80-9 3-nitro-1,5-diphenylformazan 
• 67-64-1 acetone 
• 11065-31-9 2,3-diphenyl-2,3-dihydrotetrazolium-5-thiolate 
• 147-84-2 Diethyldithiocarbamic acid 
• 25210-27-9 bis(1,5-diphenylformazan-3-yl) disulfide 
• 1234510-08-7 potassium dithizonate 
• 62-53-3 aniline 
• 2684-02-8 benzenediazonium 
• 100-63-0 phenylhydrazine 
• 50878-38-1 methyl 2-phenylhydrazinecarbodithioate 

Downstream Products

• 17883-57-7 3-phenyl-5-phenylazo-3H-[1,3,4]thiadiazol-2-one 
• 11065-31-9 2,3-diphenyl-2,3-dihydrotetrazolium-5-thiolate 
• 645-48-7 1-phenyl-3-thiosemicarbazide 
• 74298-50-3 6-(Methylthio)-4-phenyl-2-(phenylazo)-4H-1,3,4-pyrimido<4,5-e>thiadiazine 
• 62-53-3 aniline 
• 74298-54-7 4-Phenyl-2-(phenylazo)-4H-1,3,4-quinoxalino<2,3-e>thiadiazine 
• 14783-59-6 mercury(II) dithizonate, keto-form 
• 108674-68-6 1,5-diphenyl-thiocarbazone; lead (II)-salt 

Relevant articles and documents

Synthesis and kinetics of sterically altered photochromic dithizonatomercury complexes

Following a previous study where 12 electronically altered dithizones were synthesized, here we report on attempts to synthesize 26 dithizones. The purpose was to explore the boundaries within which dithizones may be synthesized, explore spectral tuning possibilities, and investigate steric effects on the photochromic reaction of its mercury complexes. Contrary to expectation, large substituents like phenoxy groups increased the rate of the photochromic back-reaction. In the series H-, 2-CH3-, 4-CH3-, 3,4-(CH3)2-, 2-OC6H5-, and 4-OC6H5-dithizonatophenylmercury(II), the lowest rate of 0.0004 s-1 was measured for the 2-CH3 complex, while the rate for the 2-OC6H5 derivative was 20 times higher. A solvent study revealed a direct relationship between dipole moment and the rate of the back-reaction, while the relationship between temperature and rate is exponential, with t1/2 = 2 min 8 s for the 4-phenoxy complex. The crystal structures of two dithizone precursors, 2-phenoxy- and 4-phenoxynitroformazan, are reported. (Figure Presented).

Chemical and electrochemical oxidation and reduction of dithizone

A non-aqueous electrochemical study of dithizone, H2Dz, 1, is compared with the chemical oxidation and reduction profile of this versatile ligand. Chemical oxidation of 1 by I2 initially leads to an isolatable disulfide-bridged species, (HDz)2, 22, but ultimately monomeric dehydrodithizone, Dz, 3, is formed. Electrochemically, in CH2Cl2/0.1 mol dm-3 [N(nBu)4][B(C6F5)4], two oxidation processes are observed for 1. Evidence of the electrochemical formation of the dimer 22 was found, but on a CV timescale the fully oxidized species, 22 oxidized, did not convert to the chemically stable species 3. Regeneration of 1 during an irreversible electrochemical reduction of the electrochemically generated fully oxidized species, 22 oxidized, was detected. Two further one-electron electrochemical irreversible reduction steps were also identified to ultimately generate H3Dz-, 8, one of the synthetic precursors to 1. In contrast, resolution and identification of the electron transfer steps of 1 in both dimethylsulfoxide, DMSO, or in CH2Cl2/0.1 mol dm-3 [N(nBu)4][PF6] were hampered by solvation and ion paring of [PF6]- especially with the oxidized species of 1. A metathesis of water-soluble potassium dithizonate, KHDz, 4b, led to lipophilic [N(nBu)4][HDz], 4c.

One-Step Conversation of Mesoionic Olate to Thiolate by Lawesson's Reagent

Treatment of mesoionic olates with Lawesson's reagent provides a convenient one-step conversion to mesoionic thiolates.