Dithiobiuret

Dithiobiuret

Names
Preferred IUPAC name 2-Imido-1,3-dithiodicarbonic diamide
Identifiers
CAS Number	541-53-7 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL501562 Y
ChemSpider	2039482 Y
ECHA InfoCard	100.007.987
EC Number	208-784-8
MeSH	2,4-dithiobiuret
PubChem CID	2758725
RTECS number	EC1575000
UNII	T40X2KXL53 Y
UN number	2811
CompTox Dashboard (EPA)	DTXSID2034968
InChI InChI=1S/C2H5N3S2/c3-1(6)5-2(4)7/h(H5,3,4,5,6,7) Y Key: JIRRNZWTWJGJCT-UHFFFAOYSA-N Y
SMILES NC(=S)NC(N)=S
Properties
Chemical formula	C2H5N3S2
Molar mass	135.20 g·mol−1
Appearance	White crystals
Density	1.54 g/cm3
log P	−0.415
Acidity (pKa)	11.152
Basicity (pKb)	2.845
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H330
Precautionary statements	P260, P280, P284, P302+P350, P310
Related compounds
Related compounds	Biuret Biguanide Thiourea
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dithiobiuret is an organosulfur compound with the formula HN(C(S)NH₂)₂. It is a colourless solid that is soluble in warm water and polar organic solvents. It is a planar molecule with short C-S and C-N distances (1.69, 1.38 Å, resp.) indicative of multiple C-S and C-N bonding.^[1]

The compound can be viewed as the product from the condensation of two molecules of thiourea, but it is prepared by treatment of 2-cyanoguanidine with hydrogen sulfide. The conversion proceeds via guanylthiourea:

NCNC(NH₂) + H₂S → HN(C(S)NH₂)(C(NH)NH₂)

HN(C(S)NH₂)(C(NH)NH₂) + H₂S → HN(C(S)NH₂)₂

It is used as a plasticizer, a rubber accelerator, and as an intermediate in pesticide manufacturing.^[2] It is extremely toxic; exposure can result in respiratory failure.