Oxamide

{{Distinguish|Oxanamide}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424752655 | Name = Oxamide | ImageFileL1 = Oxalamide 200.svg | ImageSizeL1 = 120px | ImageNameL1 = Oxamide | ImageFileR1 = Oxamide-3D-vdW.png | ImageSizeR1 = 120px | ImageNameR1 = Oxamide | PIN = Oxamide<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 841 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> | SystematicName = Ethanediamide | OtherNames = {{ubl|Oxalamide|Oxamimidic acid|Diaminoglyoxal|Oxalic acid diamide|1-Carbamoyl-formimidic acid}} |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 471-46-5 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = SBE4M0223E | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 48248 | SMILES = NC(=O)C(N)=O | EINECS = 207-442-5 | PubChem = 10113 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 9709 | InChI = 1/C2H4N2O2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6) | InChIKey = YIKSCQDJHCMVMK-UHFFFAOYAL | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C2H4N2O2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = YIKSCQDJHCMVMK-UHFFFAOYSA-N }} |Section2={{Chembox Properties | Formula = {{chem2|(CONH2)2}} | MolarMass = 88.0654 g/mol | MagSus = −39.0·10−6 cm3/mol | Appearance = White powder | MeltingPtC = 122 | MeltingPt_notes =<ref>{{cite web | url=http://www.chemspider.com/Chemical-Structure.9709.html | title=Oxamide | C2H4N2O2 | ChemSpider }}</ref> | BoilingPtC = 324 | BoilingPt_notes =,<ref>{{cite web | url=http://www.chemspider.com/Chemical-Structure.9709.html | title=Oxamide | C2H4N2O2 | ChemSpider }}</ref> decomposes above 350 °C | Solubility = Slightly soluble | Solvent = | SolubleOther = Soluble in ethanol, insoluble in diethyl ether | Density = 1.667 g/cm3 }} |Section7={{Chembox Hazards | ExternalSDS = | GHSPictograms = | GHSSignalWord = | HPhrases = {{HPhrases|}} | PPhrases = {{PPhrases|}} | GHS_ref = <ref>GHS: [https://web.archive.org/web/20211211131106/https://www.sigmaaldrich.com/NL/en/product/SIAL/75770 Sigma-Aldrich 75770]</ref> | FlashPt = > | FlashPtC = 300 }} }}

'''Oxamide''' is the organic compound with the formula {{chem2|(CONH2)2}}. This white crystalline solid is soluble in ethanol, slightly soluble in water and insoluble in diethyl ether. Oxamide is the diamide derived from oxalic acid, and the hydrate of cyanogen.

==Preparation== Oxamide is produced from hydrogen cyanide, which is oxidized to cyanogen, which is then hydrolyzed.<ref name=Ullmann>{{Ullmann|first1=Wilhelm |last1=Riemenschneider|first2=Minoru|last2=Tanifuji|title=Oxalic Acid|year=2002|doi=10.1002/14356007.a18_247}}.</ref>

It can also be prepared from formamide by glow-discharge electrolysis.<ref>{{Cite journal | doi = 10.1021/jo01057a516| title = A New Method for the Preparation of Oxamide| journal = The Journal of Organic Chemistry| volume = 27| issue = 10| pages = 3698| year = 1962| last1 = Brown | first1 = E. H. | last2 = Wilhide | first2 = W. D. | last3 = Elmore | first3 = K. L. }}</ref>

==Application== The main application is as a substitute for urea in fertilizers. Oxamide hydrolyzes (releases ammonia) very slowly, which is sometimes preferred vs the quick release by urea.

It is used as a stabilizer for nitrocellulose preparations. It also finds use in APCP rocket motors as a high performance burn rate suppressant. The use of oxamide in concentrations of 1-3 wt% has shown to slow the linear burn rate while having minimal impact on propellant specific impulse.

''N'',''N'-''substituted oxamides are supporting ligands for the copper-catalyzed amination and amidation of aryl halides in Ullmann-Goldberg reaction, including relatively unreactive aryl chloride substrates.<ref>{{Cite journal|last1=Zhou|first1=Wei|last2=Fan|first2=Mengyang|last3=Yin|first3=Junli|last4=Jiang|first4=Yongwen|last5=Ma|first5=Dawei|date=2015-09-23|title=CuI/Oxalic Diamide Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amines|journal=Journal of the American Chemical Society|volume=137|issue=37|pages=11942–11945|doi=10.1021/jacs.5b08411|pmid=26352639|bibcode=2015JAChS.13711942Z |issn=0002-7863}}</ref>

==Reactions== It dehydrates above 350 °C releasing cyanogen. Oxamide derivatives form self-assembled monolayers consisting of a hydrogen bonded network.<ref>Nguyen T.L., Fowler F.W., Lauher J.W., "Commensurate and incommensurate hydrogen bonds. An exercise in crystal engineering." ''Journal of the American Chemical Society'', '''123'''(44), pp. 11057-64, 2001. {{doi|10.1021/ja016635v}}</ref>

==References== {{reflist}}

Category:Carboxamides