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

Chemical Properties

dark brown or black crystals

Uses

Different sources of media describe the Uses of 60-10-6 differently. You can refer to the following data:
1. Dithizone is an organosulfur compound that acts as a chelating agent and forms complexes with metals such as lead and mercury. Dithizone is used to assess the purity of human pancreatic islet preparations used for transplantation into patients with type 1 diabetes.
2. Sensitive reagent for several heavy metals, Co, Cu, Pb, and Hg; especially for the estimation of minute amounts of Pb.
3. Dithizone is used as an indicator for minute amounts of lead. It acts as a chelating agent for heavy metal poisoning. As a ligand, it forms complexes with metals like zinc, lead and mercury. Further, it is used to assess the purity of human pancreatic islet preparations, which is used for transplantation in patients with type 1 diabetes. In addition to this, it is used as a titrant in the quantitative determination of heavy metals.

General Description

Dithizone (Diphenylthiocarbazone) is used as chelating agent for zinc. It is widely used for the liquid-liquid and solid phase extraction of various metals since it forms stable complexes with the metals.

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

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

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 
• 74298-47-8 4-Phenyl-2-(phenylazo)-4H-1,3,4-pyrido<3,2-e>thiadiazine 
• 74298-50-3 6-(Methylthio)-4-phenyl-2-(phenylazo)-4H-1,3,4-pyrimido<4,5-e>thiadiazine 
• 83755-85-5 1,5-diphenyl-3-trideuteriomethylthioformazan 
• 70942-88-0 3-carboxymethylthio-1,5-diphenylformazan 
• 74298-54-7 4-Phenyl-2-(phenylazo)-4H-1,3,4-quinoxalino<2,3-e>thiadiazine 
• 73761-58-7 3-(2-carboxyethylthio)-1,5-diphenylformazan 
• 73761-59-8 3-(1-carboxyethylthio)-1,5-diphenylformazan 
• 73761-55-4 5-carboxymethylthio-2,3-diphenyltetrazolium chloride 
• 73761-57-6 5-(1-Carboxyethylthio)-2,3-diphenyltetrazolium bromide 
• 73761-56-5 5-(2-carboxyethylthio)-2,3-diphenyltetrazolium bromide 
• 36539-86-3 silver dithizonate 

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.