Nitroguanidine: Difference between revisions

| verifiedrevid = 444026737

| ImageSizeL1 = 120px

| ImageSizeR1 = 100px

| OtherNames = Picrite

| Section1 = {{Chembox Identifiers

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

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem = 11174

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

| Section2={{Chembox Properties

| Formula = CH₄N₄O₂

| MolarMass = 104.07 g/mol

| Appearance = Colorless crystalline solid

| Density =

| MeltingPtC = 232

| BoilingPt = 250 °C (decomp.)

| Solubility =

| Section4 = {{Chembox Explosive

| ShockSens =

| FrictionSens =

| ExplosiveV =

| REFactor =

| Section7 = {{Chembox Hazards

| ExternalMSDS =

| EUIndex = Not listed

| MainHazards = Explosive

| FlashPt =

| Autoignition =

| Section8 = {{Chembox Related

| OtherFunctn =

| Function =

| OtherCpds = [[Guanidine]]<br>[[Guanidine nitrate]]

'''Nitroguanidine''' is a chemical compound. It is a colorless, crystalline solid. It melts at 232 °C and decomposes at 250 °C. It is not flammable and is an extremely low sensitivity explosive; however, its [[detonation velocity]] is high.

Nitroguanidine is manufactured from [[guanine]], a naturally-occurring substance typically found in the excrement of bats and birds ([[guano]]). Guanine is extracted from the droppings and is then oxidized to form [[guanidine]].<ref>{{cite journal| first=A| last=Strecker| title=Untersuchungen über die chemischen Beziehungen zwischen Guanin, Xanthin, Theobromin, Caffein und Kreatinin| journal=Annalen der Chemie und Pharmacie| volume=118| pages= 151–177| year=1861| doi=10.1002/jlac.18611180203}}</ref> Guanidine is then nitrated to form nitroguanidine. The detailed process used to perform industrial-scale synthesis is considered proprietary and is not available for public release. A laboratory synthesis involves the fusion of [[sulfamic acid]] with [[urea]], followed by nitration of the formed guanidine sulfate.<ref>{{cite web

| url=http://www.sciencemadness.org/talk/viewthread.php?tid=8911

| title=Nitroguanidine: from sulphamic acid and urea| author = Axt | work= Sciencemadness Discussion Board

| date=August 1, 2007}}</ref>

Nitroguanidine is used as an explosive [[propellant]], notably in ''triple-base'' [[smokeless powder]]. The nitroguanidine reduces the propellant's flash and flame temperature without sacrificing chamber pressure. These are typically used in large bore guns where barrel erosion and flash are particularly important.

Nitroguanidine and its derivatives are used as [[insecticide]]s, having a comparable effect to [[nicotine]]. Derivatives include [[clothianidin]], [[dinotefuran]], [[imidacloprid]], and [[thiamethoxam]].

The nitrosoylated derivative nitrosoguanidine is often used to mutagenize bacterial cells for biochemical studies.

Nitroguanidine can exist in distinct [[tautomer]]ic forms, as a [[nitroimine]] (left) or a [[nitroamine]] (right). In solution and in the solid state, the nitroimine form predominates.<ref>{{cite journal | title = Structure of nitroguanidine: nitroamine or nitroimine? New NMR evidence from nitrogen-15 labeled sample and nitrogen-15 spin coupling constants | author = Bulusu, S.; Dudley, R. L.; Autera, J. R. | journal = Magnetic Resonance in Chemistry | year = 1987 | volume = 25 | issue = 3 | pages = 234–238}}</ref><ref>{{cite journal | title = Structures of nitroso- and nitroguanidine x - ray crystallography and computational analysis | author = Murmann, R. K.; Glaser, Rainer; Barnes, Charles L. | journal = Journal of Chemical Crystallography | year = 2005 | volume = 35 | issue = 4 | pages = 317–325}}</ref>

:[[File:Nitroguanidine tautomers.svg|left|300px]]{{clear-left}}

[[Category:Guanidines]]

[[Category:Nitroamines]]

[[da:Nitroguanidin]]

[[de:Nitroguanidin]]

[[fr:Nitroguanidine]]

[[lt:Nitroguanidinas]]

[[ja:ニトログアニジン]]

[[pl:Nitroguanidyna]]