dithiooxamide

{{Chembox

| verifiedrevid = 424770522

| ImageFile = Dithiooxamide.svg

| ImageSize = 160px

| ImageAlt = Structural formula of dithiooxamide

| ImageFile1 = Dithiooxamide 3D ball.png

| ImageSize1 = 170px

| ImageAlt1 = Ball-and-stick model of the dithiooxamide molecule

| PIN = Ethanedithioamide

| OtherNames = dithiooxamide, rubeanic acid

|Section1={{Chembox Identifiers

| InChI = 1/C2H4N2S2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6)

| InChIKey = OAEGRYMCJYIXQT-UHFFFAOYAT

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C2H4N2S2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OAEGRYMCJYIXQT-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 79-40-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = HE28T8Z08D

| PubChem = 2777982

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2058248

| SMILES = S=C(N)C(=S)N

}}

|Section2={{Chembox Properties

| C=2 | H=4 | N=2 | S=2

| Appearance =

| Density = 1.523 g/cm³

| MeltingPtC = 170

| MeltingPt_notes = decomp

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| ExternalSDS = [http://msds.chem.ox.ac.uk/DI/dithiooxamide.html External MSDS]

| GHSPictograms = {{GHS07}}

| GHSSignalWord = warning

| HPhrases = {{HPhrases|H302|H315|H319|H335}}

| PPhrases = {{PPhrases|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}}

| GHS_ref = GHS: [https://pubchem.ncbi.nlm.nih.gov/compound/2777982 PubChem]

| FlashPt =

| AutoignitionPt =

}}

}}

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.{{cite web |url=http://stainsfile.info/StainsFile/stain/pigment/rubeanic-howell.htm |title=Stainsfile - Howell's rubeanic acid for copper |website=stainsfile.info |url-status=dead |archive-url=https://web.archive.org/web/20060213210752/http://stainsfile.info/StainsFile/stain/pigment/rubeanic-howell.htm |archive-date=2006-02-13}} {{Cite web|url=http://www.ojp.usdoj.gov/nij/training/firearms-training/module12/fir_m12_t05_03_f.htm|title=Strengthen science. Advance justice}} It has also been used as a building block in the synthesis of cyclen.{{OrgSynth | title = 1,4,7,10-Tetraazacyclododecane | author = David P. Reed and Gary R. Weisman | collvol = 10 | collvolpages = 667 | year = 2004 | prep = v78p0073}}