Dithiobiuret

Dithiobiuret

Skeletal formula of dithiobiuret
Names
IUPAC name Dicarbonodithioimidic diamide
Identifiers
CAS Number	541-53-7 Y
ChEMBL	ChEMBL501562 Y
ChemSpider	2039482 Y
EC Number	208-784-8
Jmol 3D model	Interactive image Interactive image
MeSH	2,4-dithiobiuret
PubChem	2758725
RTECS number	EC1575000
UN number	2811
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 [nH2]:c(:[s]):[nH]:c(:[nH2]):[s] 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
Vapor pressure	{{{value}}}
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 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.

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. It is extremely toxic; exposure can result in respiratory failure.

See also

• Biuret

External links

• Dithiobiuret at www.chemicalbook.com.