| Revision as of 21:36, 18 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 20:00, 18 September 2023 edit undoMarbletan (talk | contribs)Extended confirmed users5,415 edits Oxalamide 200.svg |
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{{Distinguish|Oxanamide}} |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 367758768 |
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| Watchedfields = changed |
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| Name = Oxamide |
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| verifiedrevid = 424752655 |
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| ImageFileL1 = Oxamide.png |
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| Name = Oxamide |
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| ImageSizeL1 = 120px |
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| ImageFileL1 = Oxalamide 200.svg |
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| ImageNameL1 = Oxamide |
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| ImageSizeL1 = 120px |
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| ImageFileR1 = Oxamide-3D-vdW.png |
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| ImageNameL1 = Oxamide |
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| ImageSizeR1 = 120px |
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| ImageNameR1 = Oxamide |
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| ImageFileR1 = Oxamide-3D-vdW.png |
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| ImageSizeR1 = 120px |
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| IUPACName = Ethanediamide |
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| ImageNameR1 = Oxamide |
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| OtherNames = Oxamide<br />Oxalamide<br />Oxamimidic acid<br />Diaminoglyoxal<br />Oxalic acid diamide<br />1-Carbamoyl-formimidic acid |
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| PIN = Oxamide<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 841 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = Ethanediamide |
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| CASNo = 471-46-5 |
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| OtherNames = {{ubl|Oxalamide|Oxamimidic acid|Diaminoglyoxal|Oxalic acid diamide|1-Carbamoyl-formimidic acid}} |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 471-46-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = SBE4M0223E |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 48248 |
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| SMILES = NC(=O)C(N)=O |
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| EINECS = 207-442-5 |
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| PubChem = 10113 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 9709 |
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| InChI = 1/C2H4N2O2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6) |
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| InChIKey = YIKSCQDJHCMVMK-UHFFFAOYAL |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C2H4N2O2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = YIKSCQDJHCMVMK-UHFFFAOYSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = {{chem2|(CONH2)2}} |
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| Formula = C<sub>2</sub>H<sub>4</sub>N<sub>2</sub>O<sub>2</sub> |
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| MolarMass = 88.0654 g/mol |
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| MolarMass = 88.0654 g/mol |
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| MagSus = −39.0·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Appearance = White powder |
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| Appearance = White powder |
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| Solubility = Soluble |
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| MeltingPtC = 122 |
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| Solvent = |
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| MeltingPt_notes =<ref>{{cite web | url=http://www.chemspider.com/Chemical-Structure.9709.html | title=Oxamide | C2H4N2O2 | ChemSpider }}</ref> |
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| SolubleOther = ] |
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| BoilingPtC = 324 |
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| Density = 1.667 g/cm<sup>3</sup> |
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| BoilingPt_notes =,<ref>{{cite web | url=http://www.chemspider.com/Chemical-Structure.9709.html | title=Oxamide | C2H4N2O2 | ChemSpider }}</ref> decomposes above 350 °C |
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}}<!-- |
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| Solubility = Slightly soluble |
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| Solvent = |
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| SolubleOther = Soluble in ], insoluble in ] |
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| Density = 1.667 g/cm<sup>3</sup> |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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| Section7 = {{Chembox Hazards |
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| GHSPictograms = |
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| GHSSignalWord = |
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| EUClass = Mild Irritant ('''6.1''') |
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| RPhrases = {{R36}} |
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| HPhrases = {{HPhrases|}} |
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| SPhrases = {{S25}} |
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| PPhrases = {{PPhrases|}} |
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| GHS_ref = <ref>GHS: {{dead link|date=December 2021}}</ref> |
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| FlashPt = >300 °C |
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| FlashPt = > |
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| FlashPtC = 300 |
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'''Oxamide''' is the ] with the formula (CONH<sub>2</sub>)<sub>2</sub>. This white ] ] is soluble in ], slightly soluble in ] and insoluble in ]. Oxamide is the di] derived from ]. |
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'''Oxamide''' is the ] with the formula {{chem2|(CONH2)2}}. This white ] ] is soluble in ], slightly soluble in ] and insoluble in ]. Oxamide is the ] derived from ], and the hydrate of ]. |
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==Preparation== |
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==Production and applications== |
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Oxamide is produced from ], which is oxidized to cyanogen, which is then hydrolyzed.<ref name=Ullmann>Wilhelm Riemenschneider, Minoru Tanifuji "Oxalic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. {{DOI| 10.1002/14356007.a18_247}}.</ref> |
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Oxamide is produced from ], which is oxidized to ], 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> |
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It can also be prepared from ] 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> |
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The main application is as substitute ] in fertilizers. Oxamide hydrolyzes (releases ammonia) very slowly, which is sometimes preferred vs the quick release by urea. |
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==Application== |
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It is used as a stabilizer for nitrocellulose preparations. It also finds use in ] ]s 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 ]. |
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The main application is as a substitute for ] in fertilizers. Oxamide hydrolyzes (releases ammonia) very slowly, which is sometimes preferred vs the quick release by urea. |
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It is used as a stabilizer for nitrocellulose preparations. It also finds use in ] ]s 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 ]. |
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''N'',''N'-''substituted oxamides are supporting ] for the copper-catalyzed ] and ] of ] in (]), including relatively unreactive ] 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|issn=0002-7863}}</ref> |
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==Reactions== |
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==Reactions== |
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Upon heating above 350 °C, it decomposes to ] and ]. Oxamide forms ] 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." '']'', '''123'''(44), pp. 11057-64, 2001. {{doi|10.1021/ja016635v}}</ref> |
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It dehydrates above 350 °C releasing ]. Oxamide derivatives form ] 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." '']'', '''123'''(44), pp. 11057-64, 2001. {{doi|10.1021/ja016635v}}</ref> |
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==References== |
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==References== |
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{{reflist}} |
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{{Authority control}} |
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==External links== |
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