Dithiooxamide

Dithiooxamide
Names
	Preferred IUPAC name Ethanedithioamide
	Other names dithiooxamide, rubeanic acid
Identifiers
CAS Number	79-40-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	2058248 ;
ECHA InfoCard	100.001.095
PubChem CID	2777982;
UNII	HE28T8Z08D ;
CompTox Dashboard (EPA)	DTXSID3020546 ;
	InChI InChI=1S/C2H4N2S2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6) Key: OAEGRYMCJYIXQT-UHFFFAOYSA-N ; 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:
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). verify (what is ?) Infobox references

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]

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]

References

^ GHS: PubChem
^ "Stainsfile - Howell's rubeanic acid for copper". stainsfile.info. Archived from the original on 2006-02-13.
^ "Strengthen science. Advance justice".
^ David P. Reed and Gary R. Weisman (2004). "1,4,7,10-Tetraazacyclododecane". Organic Syntheses; Collected Volumes, vol. 10, p. 667.
^ McManus, Gordon D.; Rawson, Jeremy M.; Feeder, Neil; Van Duijn, Joost; McInnes, Eric J. L.; Novoa, Juan J.; Burriel, Ramon; Palacio, Fernando; Oliete, Patricia (2001). "Synthesis, crystal structures, electronic structure and magnetic behaviour of the trithiatriazapentalenyl radical, C2S3N3". Journal of Materials Chemistry. 11 (8): 1992–2003. doi:10.1039/b103303b.
^ Sayresmith, Nickolas A.; Saminathan, Anand; Sailer, Joshua K.; Patberg, Shannon M.; Sandor, Kristin; Krishnan, Yamuna; Walter, Michael G. (2019). "Photostable Voltage-Sensitive Dyes Based on Simple, Solvatofluorochromic, Asymmetric Thiazolothiazoles". Journal of the American Chemical Society. 141 (47): 18780–18790. doi:10.1021/jacs.9b08959. PMID 31660737.
^ Kanaizuka, Katsuhiko; Haruki, Rie; Sakata, Osami; Yoshimoto, Mamoru; Akita, Yasuyuki; Kitagawa, Hiroshi (2008). "Construction of Highly Oriented Crystalline Surface Coordination Polymers Composed of Copper Dithiooxamide Complexes". Journal of the American Chemical Society. 130 (47): 15778–15779. doi:10.1021/ja806799t. PMID 18983147.

[1] GHS: PubChem

[2] "Stainsfile - Howell's rubeanic acid for copper". stainsfile.info. Archived from the original on 2006-02-13.

[3] "Strengthen science. Advance justice".

[4] David P. Reed and Gary R. Weisman (2004). "1,4,7,10-Tetraazacyclododecane". Organic Syntheses; Collected Volumes, vol. 10, p. 667.

[5] McManus, Gordon D.; Rawson, Jeremy M.; Feeder, Neil; Van Duijn, Joost; McInnes, Eric J. L.; Novoa, Juan J.; Burriel, Ramon; Palacio, Fernando; Oliete, Patricia (2001). "Synthesis, crystal structures, electronic structure and magnetic behaviour of the trithiatriazapentalenyl radical, C2S3N3". Journal of Materials Chemistry. 11 (8): 1992–2003. doi:10.1039/b103303b.

[6] Sayresmith, Nickolas A.; Saminathan, Anand; Sailer, Joshua K.; Patberg, Shannon M.; Sandor, Kristin; Krishnan, Yamuna; Walter, Michael G. (2019). "Photostable Voltage-Sensitive Dyes Based on Simple, Solvatofluorochromic, Asymmetric Thiazolothiazoles". Journal of the American Chemical Society. 141 (47): 18780–18790. doi:10.1021/jacs.9b08959. PMID 31660737.

[7] Kanaizuka, Katsuhiko; Haruki, Rie; Sakata, Osami; Yoshimoto, Mamoru; Akita, Yasuyuki; Kitagawa, Hiroshi (2008). "Construction of Highly Oriented Crystalline Surface Coordination Polymers Composed of Copper Dithiooxamide Complexes". Journal of the American Chemical Society. 130 (47): 15778–15779. doi:10.1021/ja806799t. PMID 18983147.

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