| Revision as of 13:57, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 458294844 of page Semicarbazide for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 23:25, 28 September 2023 edit Trappist the monk (talk | contribs)Administrators479,366 editsm →Uses, occurrence, detection: cite repair;Tag: AWB |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 413107991 |
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| verifiedrevid = 464389084 |
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| Name = Semicarbazide |
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| Name = Semicarbazide |
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| ImageFile = Semicarbazide.png |
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| ImageFile = Semicarbazide.png |
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| ImageSize = 200px |
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| ImageSize = 150px |
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| ImageAlt = Skeletal formula of semicarbazide |
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| ImageFile1 = Semicarbazide 3D ball.png |
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| IUPACName = |
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| ImageSize1 = 160 |
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| ImageAlt1 = Ball-and-stick model of the semicarbazide molecule |
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| IUPACName = Aminourea<ref>{{PubChem|5196}}</ref> |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo = 57-56-7 |
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| CASNo = 57-56-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII = 37QUC23K2X |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 28306 |
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| ChEBI = 28306 |
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| SMILES = C(=O)(N)NN |
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| SMILES = C(=O)(N)NN |
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| MolarMass = 75.08 g/mol |
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| MolarMass = 75.08 g/mol |
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| Density = |
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| MeltingPt = 96 °C |
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| GHSPictograms = {{GHS06}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|315|319|335|}} |
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| PPhrases = {{P-phrases|261|264|270|271|280|301+310|302+352|304+340|305+351+338|312|330|332+313|337+313|362|403+233|405|}} |
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| NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0 |
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'''Semicarbazide''' is the chemical compound with the formula OC(NH<sub>2</sub>)(N<sub>2</sub>H<sub>3</sub>). It is a water-soluble white solid. It is a derivative of ]. |
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==Synthesis== |
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The compound prepared by treating ] with ]:<ref name=Ullmann>Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. {{doi|10.1002/14356007.a13_177}}.</ref> |
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:OC(NH<sub>2</sub>)<sub>2</sub> + N<sub>2</sub>H<sub>4</sub> → OC(NH<sub>2</sub>)(N<sub>2</sub>H<sub>3</sub>) + NH<sub>3</sub> |
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A further reaction can occur to give ]: |
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:OC(NH<sub>2</sub>)(N<sub>2</sub>H<sub>3</sub>) + N<sub>2</sub>H<sub>4</sub> → OC(N<sub>2</sub>H<sub>3</sub>)<sub>2</sub> + NH<sub>3</sub> |
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==Derivatives== |
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Semicarbazide is frequently reacted with ]s and ]s to produce ]s via a ]. This is an example of ] formation resulting from the reaction of a primary amine with a ]. The reaction is useful because semicarbazones, like ]s and ], typically have high melting points and ], facilitating purification or identification of reaction products.<ref>{{cite book|title=Organic Chemistry|author=John McMurry|year=1984|publisher=Brooks/Cole|page=676}}</ref> |
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==Properties== |
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Semicarbazide products (semicarbazones and thiosemicarbazones) are known to have an activity of ], ] and ] through binding to ] or ] in cells. |
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==Uses, occurrence, detection== |
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Semicarbazide is used in preparing ] including ] ]s (], ], ]) and related compounds. It is also a product of degradations of the blowing agent ] (ADC). Semicarbazide forms in heat-treated flour containing ADC as well as breads made from ADC-treated flour.<ref>{{cite journal|last1=Becalski|first1=Adam|last2=Lau|first2=Benjamin|last3=Lewis|first3= David|last4=Seaman|first4=Stephen|title=Semicarbazide Formation in Azodicarbonamide-Treated Flour: A Model Study|journal=J. Agric. Food Chem.|date=2004|volume=52|issue=18|pages=5730–4|doi=10.1021/jf0495385|pmid=15373416}}</ref><ref>{{cite journal|title=Semicarbazide: occurrence in food products and state-of-the-art in analytical methods used for its determination|journal=Anal. Bioanal. Chem.|year=2005|volume=382|issue=4|pages=968–977 |author=Maria Beatriz de la Calle |author2=Elke Anklam |doi=10.1007/s00216-005-3243-z|pmid=15947918|s2cid=10765283}}</ref> |
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Semicarbazide is used as a detection reagent in ] (TLC). Semicarbazide stains α-keto acids on the TLC plate, which can then be viewed under ] light. |
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== See also == |
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* ] - another product of reaction of ] with ] |
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* ] - structurally related with the general formula (R<sub>2</sub>NNH)<sub>2</sub>C(O) |
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* ] |
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* ] |
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== References == |
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{{Reflist|2}} |
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== External links == |
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* |
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{{Hydrazines}} |
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{{GABAergics}} |
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] |
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] |
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] |
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] |