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;
UNII	NJZ2CJ4D6P ;
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 (SDS)	External MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Dithizone is a sulfur-containing organic compound. It is a good ligand, and forms complexes with many toxic metals such as lead, thallium[1] and mercury.

Dithizone may be prepared by reacting phenylhydrazine with carbon disulfide, followed by reaction with potassium hydroxide.[2]

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.[3]

Dithizone
Dithizone in Ethanol 96%

References

Bendl BJ (1969) Thallium poisoning: report of a case successfully treated with dithizone. Arch Dermatol 100:443–446 URL=https://jamanetwork.com/journals/jamadermatology/article-abstract/531202
John H. Billman and Elizabeth S. Cleland (1955). "Dithizone". Organic Syntheses.; Collective Volume, vol. 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] Bendl BJ (1969) Thallium poisoning: report of a case successfully treated with dithizone. Arch Dermatol 100:443–446 URL=https://jamanetwork.com/journals/jamadermatology/article-abstract/531202

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

[3] 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.