556-88-7

Basic information

• Product Name: Nitroguanidine
• Synonyms: Guanidine,nitro- (8CI,9CI);2-Nitroguanidine;N1-Nitroguanidine;NQ;NSC 41036;Nitroguanidine;N''-Nitroguanidine;Picrite;Picrite (propellant);a-Nitroguanidine;b-Nitroguanidine
• CAS NO: 556-88-7
• Molecular Formula: CH₄N₄O₂
• Molecular Weight: 104.06806
• EINECS: 209-143-5
• Mol File: 556-88-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 239℃
• Boiling Point: 219.348 °C at 760 mmHg
• Flash Point: 86.459 °C
• Appearance: white needle crystal
• Density: 2.009 g/cm³
• Vapor Pressure: 0.12mmHg at 25°C
• Refractive Index: 1.685
• Water Solubility: 3 g/L (20℃)
• CAS DataBase Reference: Nitroguanidine(CAS DataBase Reference)
• NIST Chemistry Reference: Nitroguanidine(556-88-7)
• EPA Substance Registry System: Nitroguanidine(556-88-7)

Safety Data

• Hazard Codes: F:Flammable;;
• Statements: R11:; R36/37/38:; R5:
• Safety Statements: S16:; S26:; S37/39:; S47:
• Hazardous Substances Data: 556-88-7(Hazardous Substances Data)

Usage

General Description

Nitroguanidine is a chemical compound with the formula CH4N4O2. It is primarily used as a high-energy propellant in the production of explosives, such as Erythritol tetranitrate (ETN), which is commonly used in military and commercial applications. Nitroguanidine is also used as a precursor in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. Although it is considered relatively stable, nitroguanidine can pose health hazards if not handled properly, as it can produce toxic fumes and can be harmful if ingested, inhaled, or absorbed through the skin.

InChI:InChI=1/CH4N4O2/c2-1(3)4-5(6)7/h(H4,2,3,4)

Synthetic route

guanidine nitrate (506-93-4) → nitroguanidine (556-88-7)

Conditions	Yield
With sulfuric acid at 20℃;	100%
With 15-crown-5; nitric acid at 5 - 32℃; for 0.666667h; Reagent/catalyst; Temperature;	99.4%
With sulfuric acid

nitro-azidocarboxamidine (62154-79-4) → nitroguanidine (556-88-7)

Conditions	Yield
With sodium dithionite

nitrosoguanidine (674-81-7) → nitroguanidine (556-88-7)

Conditions	Yield
With potassium permanganate; nitric acid

guanidinium thiocyanate (593-84-0) → nitroguanidine (556-88-7)

Conditions	Yield
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid

guanidinium sulfate (594-14-9) → nitroguanidine (556-88-7)

Conditions	Yield
With sulfuric acid; nitric acid at 20℃;
With sulfuric acid; nitric acid β-Form; nachfolgenden Erwaermen auf dem Wasserbad und Eingiessen in Eiswasser;
With nitric acid

nitric acid (7697-37-2) + guanidine nitrate (113-00-8) → nitroguanidine (556-88-7)

Conditions	Yield
reagiert das Guanidinsalz;

3-amino-1-nitroguanidine (18264-75-0) + aqueous (NH4)2CO3 → nitroguanidine (556-88-7) + aminoguanidine (79-17-4) + hydrazine (302-01-2) + diaminoguanidine

Conditions	Yield
Produkt 5: Guanidin;

α-form of nitroguanidine → nitroguanidine (556-88-7)

Conditions	Yield
β-Form; neben anderen Produkten;

β-nitroguanidine → nitroguanidine (556-88-7)

Conditions	Yield
With sulfuric acid; water α-Form;

benzenesulfonate guanylurea → nitroguanidine (556-88-7)

Conditions	Yield
With nitric acid

nitrosoguanidine (674-81-7) + KMnO4 → nitroguanidine (556-88-7)

Conditions	Yield
in schwach saurer Loesung;

nitrosoguanidine (674-81-7) + nitric acid (7697-37-2) + potassium permanganate → nitroguanidine (556-88-7)

phosphoric acid (86119-84-8, 7664-38-2) + guanidine nitrate (506-93-4) + P2O5 → nitroguanidine (556-88-7)

guanidinium nitrate → nitroguanidine (556-88-7)

Conditions	Yield
With phosphoric acid; phosphorus pentoxide In not given addn. of guanidinium nitrate to a mixture consisting of 85% soln. of H3PO4 and P2O5; ambient temp.;
With sulfuric acid In not given addn. of guanidinium nitrate to 96 %-soln. of H2SO4; ambient temp.;
With H2SO4 In not given addn. of guanidinium nitrate to 96 %-soln. of H2SO4; ambient temp.;
With H3PO4; P2O5 In not given addn. of guanidinium nitrate to a mixture consisting of 85% soln. of H3PO4 and P2O5; ambient temp.;

nitroguanidine (556-88-7) + methylamine sulfate (5000-40-8, 33689-83-7, 60361-87-7, 74356-25-5) → methyl nitroguanidine

Conditions	Yield
With sodium hydroxide In water	95%

2-chloro-5-(chloromethyl)pyridine (70258-18-3) + nitroguanidine (556-88-7) + ethylenediamine (107-15-3) → 1-(6-chloronicotinyl)-2-nitroiminoimidazoline (105827-78-9)

Conditions	Yield
With hydrogenchloride In ethanol; water at 50℃; for 3h; pH=4 - 5; Reagent/catalyst; Temperature; pH-value; Ionic liquid;	93%

nitroguanidine (556-88-7) + DNPM → C10H7N5O4 (201938-91-2)

Conditions	Yield
With sodium methylate In methanol for 2.5h; Heating;	92%

nitroguanidine (556-88-7) + 4-methyl-benzaldehyde (104-87-0) + malononitrile (109-77-3) → 4-amino-2-(nitroamino)-6-p-tolylpyrimidine-5-carbonitrile (1374981-19-7)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	92%

piperonal (120-57-0) + nitroguanidine (556-88-7) + malononitrile (109-77-3) → 4-amino-6-(benzo[d][1,3]dioxol-5-yl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-26-6)

Conditions	Yield
With sodium hydroxide In ethanol for 0.5h; Reflux;	92%

nitroguanidine (556-88-7) + 4-fluorobenzaldehyde (459-57-4) + malononitrile (109-77-3) → 4-amino-6-(4-fluorophenyl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-14-2)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reagent/catalyst; Reflux;	91%

nitroguanidine (556-88-7) + 4-bromo-benzaldehyde (1122-91-4) + malononitrile (109-77-3) → 4-amino-6-(4-bromophenyl)-2-(nitroamino)pyrimidine-5-carbonitrile (1374981-18-6)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	91%

nitroguanidine (556-88-7) + 4-methoxy-benzaldehyde (123-11-5) + malononitrile (109-77-3) → 4-amino-6-(4-methoxyphenyl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-22-2)

Conditions	Yield
With sodium hydroxide In ethanol for 0.5h; Reflux;	91%

nitroguanidine (556-88-7) + 3,4-dimethoxy-benzaldehyde (120-14-9) + malononitrile (109-77-3) → 4-amino-6-(3,4-dimethoxyphenyl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-24-4)

Conditions	Yield
With sodium hydroxide In ethanol for 0.5h; Reflux;	91%

nitroguanidine (556-88-7) + zinc (7440-66-6) → ammonia (7664-41-7) + hydrazine (302-01-2)

Conditions	Yield
With sodium hydroxide In acetic acid redn. with Zn dust, than heating with NaOH under reflux, 8-10 h;	A n/a B 90%
With sodium hydroxide In acetic acid redn. with Zn dust, than heating with NaOH under reflux, 8-10 h;	A n/a B 90%

nitroguanidine (556-88-7) → ammonia (7664-41-7) + hydrazinium sulfate (10034-93-2)

Conditions	Yield
With sodium hydroxide In acetic acid byproducts: Na2CO3; redn. in presence of Zn dust than reflux with NaOH for 8-10 h; cooling; react. with H2SO4;	A n/a B 90%
With sodium hydroxide In acetic acid byproducts: Na2CO3; redn. in presence of Zn dust than reflux with NaOH for 8-10 h; cooling; react. with H2SO4;	A n/a B 90%

nitroguanidine (556-88-7) + 4-chlorobenzaldehyde (104-88-1) + malononitrile (109-77-3) → 4-amino-6-(4-chlorophenyl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-15-3)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	90%

nitroguanidine (556-88-7) + 3,4-dichlorobenzaldehyde (6287-38-3) + malononitrile (109-77-3) → 4-amino-6-(3,4-dichlorophenyl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-17-5)

Conditions	Yield
With sodium hydroxide In ethanol for 0.5h; Reflux;	90%

nitroguanidine (556-88-7) + 2,4-dichlorobenzaldeyhde (874-42-0) + malononitrile (109-77-3) → 4-amino-6-(2,4-dichlorophenyl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-16-4)

Conditions	Yield
With sodium hydroxide In ethanol for 0.5h; Reflux;	89%

nitroguanidine (556-88-7) + ortho-anisaldehyde (135-02-4) + malononitrile (109-77-3) → 4-amino-6-(2-methoxyphenyl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-21-1)

Conditions	Yield
With sodium hydroxide In ethanol for 0.5h; Reflux;	89%

nitroguanidine (556-88-7) + asaraldehyde (4460-86-0) + malononitrile (109-77-3) → 4-amino-2-nitroamino-6-(3,4,5-trimethoxyphenyl)pyrimidine-5-carbonitrile

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	89%

nitroguanidine (556-88-7) + ethyl 4-(2,6-difluorophenyl)-2-methyl-3-oxobutanoate (221121-48-8) → C12H10F2N4O3

Conditions	Yield
With sodium ethanolate In ethanol for 5h; Heating;	88%

nitroguanidine (556-88-7) + benzaldehyde (100-52-7) + malononitrile (109-77-3) → 4-amino-2-nitroamino-6-phenylpyrimidine-5-carbonitrile (1374981-13-1)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	88%

nitroguanidine (556-88-7) + 2,5-dimethoxybenzaldehyde (93-02-7) + malononitrile (109-77-3) → 4-amino-6-(2,5-dimethoxyphenyl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-23-3)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	87%

3,4-dimethylbenzaldehyde (5973-71-7) + nitroguanidine (556-88-7) + malononitrile (109-77-3) → 4-amino-6-(3,4-dimethylphenyl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-20-0)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	86%

nitroguanidine (556-88-7) + ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate (221121-46-6) → C11H8F2N4O3

Conditions	Yield
With sodium ethanolate In ethanol for 5h; Heating;	85%

nitroguanidine (556-88-7) + 1-naphthaldehyde (66-77-3) + malononitrile (109-77-3) → 4-amino-6-(naphthalene-1-yl)-2-nitroaminopyrimidine-5-carbonitrile (1374981-27-7)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Reflux;	85%

nitroguanidine (556-88-7) + ethyl 2-oxocyclohexane carboxylate (1655-07-8) → 2-nitroamino-5,6,7,8-tetrahydro-4(3H)-quinazolinone (54069-45-3)

Conditions	Yield
With sodium methylate at 20℃; for 0.75h; Heating / reflux;	84%

nitroguanidine (556-88-7) + 1-isothiocyanato-4-methylbenzene (622-59-3) → 1-(4-methylphenyl)-3-(N-nitroamidino)thiourea (90559-99-2)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide 1.) r.t., 10 min, 2.) r.t., 30 min;	84%
With potassium hydroxide In N,N-dimethyl-formamide
With sodium hydroxide In dimethyl sulfoxide for 1h;
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1.5h;

nitroguanidine (556-88-7) + 4-Chlorophenyl isothiocyanate (2131-55-7) → 1-(4-chlorophenyl-3-(N-nitroguanidine))thiourea

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide 1.) r.t., 10 min, 2.) r.t., 30 min;	83%
With potassium hydroxide In N,N-dimethyl-formamide
With sodium hydroxide In dimethyl sulfoxide for 1h;
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1.5h;

nitroguanidine (556-88-7) + 4-Methoxyphenyl isothiocyanate (2284-20-0) → C9H11N5O3S

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide 1.) r.t., 10 min, 2.) r.t., 30 min;	82%
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1.5h;

nitroguanidine (556-88-7) + phenyl isothiocyanate (103-72-0) → 1-(phenyl-3-(N-nitroguanidine))thiourea (90223-75-9)

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide 1.) r.t., 10 min, 2.) r.t., 30 min;	80%
With potassium hydroxide In N,N-dimethyl-formamide
With sodium hydroxide In dimethyl sulfoxide for 1h;
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1.5h;

nitroguanidine (556-88-7) + methylamine (74-89-5) → N-methyl-N'-nitroguanidine (4245-76-5)

Conditions	Yield
In water at 10 - 30℃; for 5h; Temperature; Reagent/catalyst; Sealed tube;	79.58%
at 60 - 70℃;

nitroguanidine (556-88-7) + 1-(4-chloro-2-fluorophenyl)propan-2-one → 1-(4-chloro-2-fluoro-5-nitrophenyl)propan-2-one

Conditions	Yield
With sulfuric acid at 0℃; for 2h;	78%

Upstream product

• 506-93-4 guanidine nitrate 
• 7697-37-2 nitric acid 
• 113-00-8 guanidine nitrate 
• 18264-75-0 3-amino-1-nitroguanidine 
• 86119-84-8 phosphoric acid 
• 651322-68-8 1,2-dinitroguanidine 
• 674-81-7 nitrosoguanidine 
• 594-14-9 guanidinium sulfate 
• 593-84-0 guanidinium thiocyanate 
• 62154-79-4 nitro-azidocarboxamidine 

Downstream Products

• 35091-64-6 propylnitroguanidine 
• 35089-69-1 N-nitro-N'-pentyl-guanidine 
• 4245-76-5 N-methyl-N'-nitroguanidine 
• 101250-97-9 N',N''-dimethyl-N-nitroguanidine 
• 674-81-7 nitrosoguanidine 
• 2582-30-1 aminoguanidine bicarbonate 
• 79-17-4 aminoguanidine 
• 18264-75-0 3-amino-1-nitroguanidine 
• 89977-66-2 N-benzoyl-N'-nitro-guanidine 
• 5458-83-3 N-butyl-N'-nitro-guanidine 
• 5461-84-7 3-Nitro-1-(3-dimethylamino-propyl)-guanidin 
• 102146-46-3 2-hydrazino-4,6-bis(p-methoxyphenyl)pyrimidine 
• 5465-96-3 2-(nitroimino)imidazolidine 
• 204188-33-0 1-ethyl-3-(N-nitroamidino)thiourea 

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