Dithiobiuret

Dithiobiuret

Names
IUPAC name Dicarbonodithioimidic diamide
Identifiers
CAS Registry Number	541-53-7 Y
ChEMBL	ChEMBL501562 Y
ChemSpider	2039482 Y
EC number	208-784-8
InChI InChI=1S/C2H5N3S2/c3-1(6)5-2(4)7/h(H5,3,4,5,6,7) Y Key: JIRRNZWTWJGJCT-UHFFFAOYSA-N Y
Jmol-3D images	Image Image
MeSH	2,4-dithiobiuret
PubChem	2758725
RTECS number	EC1575000
SMILES [nH2]:c(:[s]):[nH]:c(:[nH2]):[s] NC(=S)NC(N)=S
UN number	2811
Properties
Molecular formula	C2H5N3S2
Molar mass	135.21 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 pictograms
GHS signal word	DANGER
GHS hazard statements	H300, H310, H330
GHS precautionary statements	P260, P280, P284, P302+350, P310
EU classification	T+
R-phrases	R26/27/28
S-phrases	S22, S36/37, S45
Related compounds
Related compounds	Dimethylamine Trimethylamine Unsymmetrical dimethylhydrazine N-Nitrosodimethylamine Biguanide Diethylamine Triethylamine Diisopropylamine Dimethylaminopropylamine Diethylenetriamine N,N-Diisopropylethylamine Triisopropylamine Tris(2-aminoethyl)amine Mechlorethamine HN1 (nitrogen mustard) HN3 (nitrogen mustard)
Except where noted otherwise, data is 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.

See also

• Biuret

References

External links

• Williams, KD; Porter, WR; Peterson, RE (1982). "Dithiobiuret metabolism in the rat". Neurotoxicology 3 (4): 221–31. PMID 6820683. 
• Dithiobiuret at www.chemicalbook.com.