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

Chemical compound

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[edit]

* Biuret

## References[edit]

1. ^ Spofford, W. A.; Amma, E. L. (1972). "Crystal and molecular structure of dithiobiuret". Journal of Crystal and Molecular Structure. 2 (4): 151–158. doi:10.1007/BF01275491.
2. ^ Dithiobiuret Hazardous Substance Fact Sheet, New Jersey Department of Health and Senior Services

## External links[edit]

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

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H300]: H300: Fatal if swallowed
*[H310]: H310: Fatal in contact with skin
*[H330]: H330: Fatal if inhaled
*[P260]: P260: Do not breathe dust/fume/gas/mist/vapours/spray.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P284]: P284: Wear respiratory protection.
*[P302+P350]: P302+P350: IF ON SKIN: Gently wash with soap and water.
*[P310]: P310: Immediately call a POISON CENTER or doctor/physician.