Dithizone

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Dithizone
Skeletal formula of dithizone
Ball-and-stick model of the dithizone molecule
Names
IUPAC name
(1E)-3-anilino-1-phenylimino-thiourea
Other names
Diphenylthiocarbazone, 1,5-Diphenylthiocarbazone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.413 Edit this at Wikidata
  • InChI=1S/C13H12N4S/c18-13(16-14-11-7-3-1-4-8-11)17-15-12-9-5-2-6-10-12/h1-10,14H,(H,16,18)/b17-15+ checkY
    Key: UOFGSWVZMUXXIY-BMRADRMJSA-N checkY
  • InChI=1/C13H12N4S/c18-13(16-14-11-7-3-1-4-8-11)17-15-12-9-5-2-6-10-12/h1-10,14H,(H,16,18)/b17-15+
    Key: UOFGSWVZMUXXIY-BMRADRMJBA
  • S=C(/N=N/c1ccccc1)NNc2ccccc2
Properties
C13H12N4S
Molar mass 256.33 g·mol−1
Hazards
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dithizone is a sulfur-containing organic compound. It is a good ligand, and forms complexes with many metals such as lead and mercury.

Dithizone may be prepared by reacting phenylhydrazine with carbon disulfide, followed by reaction with potassium hydroxide.[1]

Dithizone is used to assess the purity of human pancreatic islet preparations used for transplantation into patients with type 1 diabetes. Dithizone binds zinc ions present in the islet's beta cells, and therefore stains the islets red. Exocrine tissue also present in the preparations does not bind dithizone, and is therefore not stained.[2]

  • Dithizone

  • Dithizone in Ethanol 96%

References[]

  1. ^ John H. Billman and Elizabeth S. Cleland (1955). "Dithizone". Organic Syntheses.; Collective Volume, 3, p. 360
  2. ^ Ricordi, C; Gray, DW; Hering, BJ; Kaufman, DB; Warnock, GL; Kneteman, NM; Lake, SP; London, NJ; et al. (1990). "Islet isolation assessment in man and large animals" (PDF). Acta Diabetologica Latina. 27 (3): 185–95. doi:10.1007/BF02581331. PMID 2075782.
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