Dithizone

Dithizone
IUPAC name (1E)-3-anilino-1-phenylimino-thiourea
Other names Diphenylthiocarbazone, 1,5-Diphenylthiocarbazone
Identifiers
CAS number	60-10-6 Y
PubChem	657262
ChemSpider	571406 Y
Jmol-3D images	Image 1
SMILES S=C(/N=N/c1ccccc1)NNc2ccccc2
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+ Y Key: UOFGSWVZMUXXIY-BMRADRMJSA-N Y 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
Properties
Molecular formula	C13H12N4S
Molar mass	256.33 g mol−1
Hazards
MSDS	External MSDS
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 transplantaion 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].

References

1. ^ John H. Billman and Elizabeth S. Cleland (1955), "Dithizone", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0360 ; Coll. Vol. 3: 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". Acta diabetologica latina 27 (3): 185–95. doi:10.1007/BF02581331. PMID 2075782.