Dithizone

Dithizone
Names
	IUPAC name (1E)-3-anilino-1-phenylimino-thiourea
	Other names Diphenylthiocarbazone, 1,5-Diphenylthiocarbazone
Identifiers
CAS Number	60-10-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	571406 ;
ECHA InfoCard	100.000.413
PubChem CID	657262;
CompTox Dashboard (EPA)	DTXSID0058770 ;
	InChI 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+ Key: UOFGSWVZMUXXIY-BMRADRMJSA-N ; 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;
	SMILES S=C(/N=N/c1ccccc1)NNc2ccccc2;
Properties
Chemical formula	C13H12N4S
Molar mass	256.33 g·mol−1
Hazards
Safety data sheet	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

John H. Billman and Elizabeth S. Cleland (1955). "Dithizone". Organic Syntheses.; Collective Volume, 3, p. 360
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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[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.