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Nitroguanidine

From Wikipedia, the free encyclopedia
Not to be confused with Guanidine nitrate.
Nitroguanidine
Names
IUPAC name
1-Nitroguanidine
Other names
Picrite
Identifiers
3D model (JSmol)
03, 126
ChEBI
ChemSpider
ECHA InfoCard 100.008.313 Edit this at Wikidata
RTECS number
  • MF4600000
UNII
  • InChI=1S/CH4N4O2/c2-1(3)4-5(6)7/h(H4,2,3,4) checkY
    Key: IDCPFAYURAQKDZ-UHFFFAOYSA-N checkY
  • InChI=1/CH4N4O2/c2-1(3)4-5(6)7/h(H4,2,3,4)
    Key: IDCPFAYURAQKDZ-UHFFFAOYAN
  • NC(N)=N[N+]([O-])=O
Properties
(NH2)2CNNO2
Molar mass 104.069 g·mol−1
Appearance Colorless crystalline solid
Density 1.77 g/cm3
Melting point 239 °C (462 °F; 512 K)[4] decomposes
  • 0.12 g/100mL (0 °C (32 °F; 273 K))
  • 0.42 g/100mL (25 °C (77 °F; 298 K))
  • 8.25 g/100mL (100 °C (212 °F; 373 K))[1]
Solubility in Sulfuric acid 10.9 g/100mL (45% H2SO4)[1]
Acidity (pKa) 12.2 (in 1 M NaCl at 24 °C (75 °F; 297 K))[2]
Basicity (pKb) 15[3]
Explosive data[1]
Shock sensitivity
  • 4.4 lb (2 kg) weight, 19 in (47 cm) (Bureau of Mines apparatus)
  • 1 lb (0.45 kg) weight, 26 in (66 cm) (Picatinny Arsenal apparatus)
  • Unaffected - Rifle bullet impact.
Friction sensitivity Insensitive
Detonation velocity
  • 5,360 m/s (17,600 ft/s) (at specific gravity (sp. gr.) 1)
  • 7,650 m/s (25,100 ft/s) (at sp. gr. 1.5)
RE factor 1.01 (Trauzl test)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Explosive when dry.
GHS labelling:(Stabilized with 25% water)[4]
GHS02: Flammable
Danger
H228
P210, P240, P241, P280, P370+P378
NFPA 704 (fire diamond)
[5]
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
2
0
4
7 mg/m3[4] (TWA)
Lethal dose or concentration (LD, LC):
10200 mg/kg (oral, rat)[5]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Nitroguanidine - sometimes abbreviated NQ or NGu - is a colorless, crystalline solid that decomposes at 239 °C (462 °F), without melting. Nitroguanidine is an extremely insensitive but powerful high explosive. Nitroguanidine is used as an energetic material (propellant or high explosive), precursor for insecticides,[citation needed] and for other purposes.

Manufacture

[edit]

Nitroguanidine is produced worldwide on a large scale starting with the reaction of dicyandiamide (DCD) with ammonium nitrate to afford the salt guanidinium nitrate, which is then nitrated by treatment with concentrated sulfuric acid at low temperature.[6]

[C(NH2)3]NO3 → (NH2)2CNNO2 + H2O

The guanidinium nitrate intermediate may also be produced via the Boatright–Mackay–Roberts (BMR) process, in which molten urea is reacted with molten ammonium nitrate in the presence of silica gel.[6][7] This process had been commercialized because of its attractive economic features.

2 NH2CONH2 + NH4NO3 → [C(NH2)3]NO3 + 2 NH3 + CO2

Uses

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Explosives

[edit]

Nitroguanidine has been in use since the 1930s as an ingredient in triple-base gun propellants in which it reduces flame temperature, muzzle flash, and erosion of the gun barrel but preserves chamber pressure due to high nitrogen content. Its extreme insensitivity combined with low cost has made it a popular ingredient in insensitive high explosive formulations (e.g AFX-453, AFX-760, IMX-101, AL-IMX-101, IMX-103, etc.).[8]

The first triple-base propellant, featuring 20-25% of nitroguanidine and 30-45% nitroglycerine, was developed at the Dynami Nobel factory at Avigliana and patented by its director Dr. Modesto Abelli (1859-1911) in 1905.[9][10]

Nitroguanidine's explosive decomposition may be given by the following idealized equation:[citation needed]

3 O2N−N=C(NH2)2 → 3 CO2 + 4 N2 + 4 NH3

Pesticides

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Nitroguanidine derivatives are used as insecticides, having a comparable effect to nicotine. Derivatives include clothianidin, dinotefuran, imidacloprid, and thiamethoxam.

Structure

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It has been confirmed by NMR spectroscopy, and both x-ray and neutron diffraction that nitroguanidine exclusively exists as the nitroimine tautomer both in solid state and solution.[11][12][13]

[edit]

The methylated and nitrosylated derivative methylnitronitrosoguanidine is used to mutagenize bacterial cells for biochemical studies.[citation needed]

References

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  1. ^ a b c Fedoroff, Basil T.; Sheffield, Oliver E. (1 January 1974). "N - Nitroguanidine". Encyclopedia of Explosives and Related Items (PDF) (Technical report). Vol. 6, Etagenguss to Gyroscopic Movement of Projectiles. Picatinny Arsenal, Dover, NJ: U.S. Army Research and Development Command TACOM - Ardec Warheads, Energetics and Combat Support Center. p. G155-6. LCCN 61-61759. ADA011845, PATR2700.
  2. ^ DeVries, John E.; Gantz, E. St. Clair (February 1954). "Spectrophotometric Studies of Dissociation Constants of Nitroguanidines, Triazoles and Tetrazoles". Journal of the American Chemical Society. 76 (4): 1008–1010. Bibcode:1954JAChS..76.1008D. doi:10.1021/ja01633a019.
  3. ^ Hall, Lila M.; De Vries, John E.; Gantz, E. St. Clair (December 1955). "Basic Equilibrium Constants of Nitroguanidine and Nitroaminoguanidine". Journal of the American Chemical Society. 77 (24): 6507–6508. Bibcode:1955JAChS..77.6507H. doi:10.1021/ja01629a024.
  4. ^ a b c Sigma-Aldrich Co., Nitroguanidine (desensitized). Retrieved on 10 December 2025.
  5. ^ a b "SDS - Nitroguanidine" (PDF). datasheets.scbt.com. 2.2. Santa Cruz Biotechnology. 30 March 2017. p. 1. Retrieved 10 December 2025.
  6. ^ a b Koch, Ernst-Christian (2019). "Insensitive High Explosives: III. Nitroguanidine – Synthesis – Structure – Spectroscopy – Sensitiveness". Propellants, Explosives, Pyrotechnics. 44 (3): 267–292. doi:10.1002/prep.201800253. ISSN 0721-3115.
  7. ^ Steele, N. W.; Doyle, J. A.; Whippen, M. G.; Gorton, J. A.; Hercules Inc. (December 1973). Process Engineering Design for Manufacture of Guanidine Nitrate (Technical report). Picatinny Arsenal. AD-772074.
  8. ^ Koch, Ernst-Christian (August 2019). "Insensitive high explosives: IV. Nitroguanidine – Initiation & detonation". Defence Technology. 15 (4): 467–487. doi:10.1016/j.dt.2019.05.009.
  9. ^ Fedoroff, Basil T.; Sheffield, Oliver E.; Clift, George D.; Reese, Earl F.; Aaronson, Henry A.; Dunkle, Cyrus G.; Walter, Hans; McLean, Dan C. (1960). "A - Abelli, Modesto". Encyclopedia of Explosives and Related Items (PDF) (Technical report). Vol. 1, A through Azoxy. Picatinny Arsenal, NJ: U.S. Army Research and Development Command TACOM - Ardec Warheads, Energetics and Combat Support Center. p. A2. LCCN 61-61759. AD0257189, PATR2700.
  10. ^ U.S. patent 899855A
  11. ^ Bulusu, S.; Dudley, R. L.; Autera, J. R. (1987). "Structure of nitroguanidine: nitroamine or nitroimine? New NMR evidence from nitrogen-15 labeled sample and nitrogen-15 spin coupling constants". Magnetic Resonance in Chemistry. 25 (3): 234–238. doi:10.1002/mrc.1260250311. S2CID 97416890.
  12. ^ Murmann, R. K.; Glaser, Rainer; Barnes, Charles L. (2005). "Structures of nitroso- and nitroguanidine x-ray crystallography and computational analysis". Journal of Chemical Crystallography. 35 (4): 317–325. Bibcode:2005JCCry..35..317M. doi:10.1007/s10870-005-3252-y. S2CID 96090647.
  13. ^ Choi, C. S. (15 October 1981). "Refinement of 2-nitroguanidine by neutron powder diffraction". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 37 (10): 1955–1957. Bibcode:1981AcCrB..37.1955C. doi:10.1107/S0567740881007735.
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