Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Semicarbazide: Difference between pages

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| verifiedrevid = 464389084

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| ImageAlt = Skeletal formula of semicarbazide

| ImageFile1 = Semicarbazide 3D ball.png

| ImageSize1 = 160

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

| IUPACName = Aminourea<ref>{{PubChem|5196}}</ref>

| UNII = 37QUC23K2X

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

| ChEBI_Ref = {{ebicite|correct|EBI}}

| MeltingPt = 96 °C

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| GHSPictograms = {{GHS06}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|301|315|319|335|}}

| 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|}}

| NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0

| ExternalSDS = [https://pubchem.ncbi.nlm.nih.gov/compound/Semicarbazide#datasheet=LCSS]

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'''Semicarbazide''' is the chemical compound with the formula OC(NH₂)(N₂H₃). It is a water-soluble white solid. It is a derivative of [[urea]].

==Synthesis==

The compound prepared by treating [[urea]] with [[hydrazine]]:<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>

:OC(NH₂)₂ + N₂H₄ → OC(NH₂)(N₂H₃) + NH₃

A further reaction can occur to give [[carbohydrazide]]:

:OC(NH₂)(N₂H₃) + N₂H₄ → OC(N₂H₃)₂ + NH₃

==Derivatives==

Semicarbazide is frequently reacted with [[aldehyde]]s and [[ketone]]s to produce [[semicarbazone]]s via a [[condensation reaction]]. This is an example of [[imine]] formation resulting from the reaction of a primary amine with a [[carbonyl group]]. The reaction is useful because semicarbazones, like [[oxime]]s and [[2,4-Dinitrophenylhydrazine|2,4-DNPs]], typically have high melting points and [[crystallize]], facilitating purification or identification of reaction products.<ref>{{cite book|title=Organic Chemistry|author=John McMurry|year=1984|publisher=Brooks/Cole|page=676}}</ref>

==Properties==

Semicarbazide products (semicarbazones and thiosemicarbazones) are known to have an activity of [[Antiviral drug|antiviral]], [[antiinfective]] and [[antineoplastic]] through binding to [[copper]] or [[iron]] in cells.

==Uses, occurrence, detection==

Semicarbazide is used in preparing [[pharmaceuticals]] including [[nitrofuran]] [[antibacterial]]s ([[furazolidone]], [[nitrofurazone]], [[nitrofurantoin]]) and related compounds. It is also a product of degradations of the blowing agent [[azodicarbonamide]] (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>

Semicarbazide is used as a detection reagent in [[thin layer chromatography]] (TLC). Semicarbazide stains α-keto acids on the TLC plate, which can then be viewed under [[ultraviolet]] light.

== See also ==

* [[Biurea]] - another product of reaction of [[urea]] with [[hydrazine]]

* [[Carbazide]] - structurally related with the general formula (R₂NNH)₂C(O)

* [[Semicarbazide-cadmium therapy]]

* [[thiosemicarbazide]]

== References ==

{{Reflist|2}}

== External links ==

* [http://www.acdlabs.com/iupac/nomenclature/79/r79_673.htm Compounds Containing a N-CO-N-N or More Complex Group]

{{Hydrazines}}

{{GABAergics}}

[[Category:Functional groups]]

[[Category:Photographic chemicals]]

[[Category:Semicarbazides| ]]

[[Category:Glutamate decarboxylase inhibitors]]