Dithiooxamide

Dithiooxamide, also known as rubeanic acid, is an organic compound. It is the sulfur analog of oxamide. It acts as a chelating agent, e.g. in the detection or determination of copper.^[2][3] It has also been used as a building block in the synthesis of cyclen.^[4]

Dithiooxamide

Names
Preferred IUPAC name Ethanedithioamide
Other names dithiooxamide, rubeanic acid
Identifiers
CAS Number	79-40-3 Y
3D model (JSmol)	Interactive image
ChemSpider	2058248 Y
ECHA InfoCard	100.001.095
PubChem CID	2777982
UNII	HE28T8Z08D Y
CompTox Dashboard (EPA)	DTXSID3020546
InChI InChI=1S/C2H4N2S2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6) Y Key: OAEGRYMCJYIXQT-UHFFFAOYSA-N Y InChI=1/C2H4N2S2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6) Key: OAEGRYMCJYIXQT-UHFFFAOYAT
SMILES S=C(N)C(=S)N
Properties
Chemical formula	C2H4N2S2
Molar mass	120.19 g·mol−1
Density	1.523 g/cm3
Melting point	170 °C (338 °F; 443 K) decomp
Hazards
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Safety data sheet (SDS)	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Materials chemistry

Rubeanic acid has received much attention as a precursor to photonic or electroactive materials. It is a precursor to inorganic C-S-N rings.^[5] It condenses with acid chlorides to thiazoles.^[6] It forms coordination polymers.^[7]