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.

Manufacture

Nitroguanidine is manufactured from guanine

Guanine

Guanine is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine . In DNA, guanine is paired with cytosine. With the formula C5H5N5O, guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with...

, a naturally-occurring substance typically found in the excrement of bats and birds (guano

Guano

Guano is the excrement of seabirds, cave dwelling bats, and seals. Guano manure is an effective fertilizer due to its high levels of phosphorus and nitrogen and also its lack of odor. It was an important source of nitrates for gunpowder...

). Guanine is extracted from the droppings and is then oxidized to form guanidine

Guanidine

Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives. It is found in urine as a normal product of protein metabolism. The molecule was first synthesized in 1861 by the oxidative degradation of an...

. 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

Sulfamic acid

Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, and sulfamidic acid, is a molecular compound with the formula H3NSO3...

 with urea

Urea

Urea or carbamide is an organic compound with the chemical formula CO2. The molecule has two —NH2 groups joined by a carbonyl functional group....

, followed by nitration of the formed guanidine sulfate.

Explosives

Nitroguanidine is used as an explosive propellant

Propellant

A propellant is a material that produces pressurized gas that:* can be directed through a nozzle, thereby producing thrust ;...

, notably in triple-base smokeless powder

Smokeless powder

Smokeless powder is the name given to a number of propellants used in firearms and artillery which produce negligible smoke when fired, unlike the older gunpowder which they replaced...

. 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.

Pesticides

Nitroguanidine and its derivatives are used as insecticide

Insecticide

An insecticide is a pesticide used against insects. They include ovicides and larvicides used against the eggs and larvae of insects respectively. Insecticides are used in agriculture, medicine, industry and the household. The use of insecticides is believed to be one of the major factors behind...

s, having a comparable effect to nicotine

Nicotine

Nicotine is an alkaloid found in the nightshade family of plants that constitutes approximately 0.6–3.0% of the dry weight of tobacco, with biosynthesis taking place in the roots and accumulation occurring in the leaves...

. Derivatives include clothianidin

Clothianidin

Clothianidin is an insecticide developed by Takeda Chemical Industries and Bayer AG. Similar to thiamethoxam and imidacloprid, it is a neonicotinoid. Neonicotinoids are a class of insecticides which act on the central nervous system of insects with lower toxicity to mammals...

, dinotefuran

Dinotefuran

Dinotefuran is an insecticide of the neonicotinoid class developed by Mitsui Chemicals for control of insect pests such as aphids, whiteflies, thrips, leafhoppers, leafminers, sawflies, mole cricket, white grubs, lacebugs, billbugs, beetles, mealybugs, and cockroaches on leafy vegetables, in...

, imidacloprid

Imidacloprid

Imidacloprid is a nicotine-based, systemic insecticide, which acts as a neurotoxin and belongs to a class of chemicals called the neonicotinoids. Although it is now off patent, the primary manufacturer of this chemical is Bayer CropScience,...

, and thiamethoxam

Thiamethoxam

Thiamethoxam is an insecticide in the class of neonicotinoids. It has a broad spectrum of activity against many types of insects.-History:Thiamethoxam was developed by Syngenta but a patent dispute arose with Bayer which already had patents covering other neonicotinoids including imidacloprid...

.

Biochemistry

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

Structure

Nitroguanidine can exist in distinct tautomer

Tautomer

Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. This reaction commonly results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond...

ic forms, as a nitroimine (left) or a nitroamine

Nitroamine

Nitroamines are organic compounds that contain the nitroamino functional group, R2N-NO2. The R's are the continuation of the ring structure, see RDX. Examples of nitroamines are the explosives HMX, cyclotrimethylene trinitramine, Hexanitrohexaazaisowurtzitane and tetryl...

(right). In solution and in the solid state, the nitroimine form predominates.