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Your Location：Home>Product Center >> Pesticide API and intermediates >> Nitroguanidine
  • Nitroguanidine
Name:Nitroguanidine
CAS No:556-88-7

PRODUCT DESCRIPTION

【Name】
Guanidine, N-nitro-
【Iupac name】
2-nitroguanidine
【CAS Registry number】
556-88-7
【Synonyms】
Guanidine,nitro- (8CI,9CI)
2-Nitroguanidine
N1-Nitroguanidine
NQ
NSC 41036
Nitroguanidine
N''-Nitroguanidine
Picrite
Picrite (propellant)
a-Nitroguanidine
b-Nitroguanidine
【EINECS(EC#)】
209-143-5
【Molecular Formula】
CH4N4O2 (Products with the same molecular formula)
【Molecular Weight】
104.07
【Inchi】
InChI=1/CH4N4O2/c2-1(3)4-5(6)7/h(H4,2,3,4)
【Canonical SMILES】
C(=N[N+](=O)[O-])(N)N
【MOL File】
556-88-7.mol

Chemical and Physical Properties

【Appearance】
white needle crystal
【Density】
2 g/cm3
【Melting Point】
239 °C (dec.)(lit.)
【Boiling Point】
323.3 °C at 760 mmHg
【Refractive Index】
1.685
【Flash Point】
149.3 °C
【Water】
3 G/L (20 ºC)
【Solubilities】
soluble (easily soluble in alkali solution )
【Color/Form】
Exists in two forms, alpha and beta.
alpha: needles, prisms from water
long thin flat, flexible, lustrous needles (alpha); small, thin elongated plates (beta)
【Stability】
Stable under normal temperatures and pressures.
【Storage temp】
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area.
【Spectral properties】
MAX ABSORPTION (WATER): 264 NM (LOG E= 4.16)
IR: 21412 (Sadtler Research Laboratories Prism Collection)
UV: 6-1 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
MASS: 40 (Aldermaston, Eight Peak Index of Mass Spectra, UK)
【Computed Properties】
Molecular Weight:104.06806 [g/mol]
Molecular Formula:CH4N4O2
XLogP3-AA:-1
H-Bond Donor:2
H-Bond Acceptor:3
Rotatable Bond Count:0
Tautomer Count:2
Exact Mass:104.033425
MonoIsotopic Mass:104.033425
Topological Polar Surface Area:110
Heavy Atom Count:7
Formal Charge:0
Complexity:96.7
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:2
Feature 3D Cation Count:1
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:3

Safety and Handling

【Hazard Codes】
F: Flammable;Xi: Irritant;
【Risk Statements】
R11;R36/37/38;R5
【Safety Statements 】
16-26-33-36/37/39-47-37/39
【HazardClass】
1.1D
【Safety】

Poison by intraperitoneal route. Moderately toxic by ingestion. Mutation data reported. A very dangerous fire hazard when exposed to heat, flame, or by chemical reaction with oxidizers. A severe explosion hazard when shocked or exposed to heat or flame. It is about as powerful as TNT. It is normally mixed with colloided nitrocellulose or ammonium nitrate and paraffin wax. Can react vigorously with oxidizing materials and the derivatives can be explosive. The mercury and silver salts and other derivatives are much more impact-sensitive. When heated to decomposition it emits highly toxic fumes of NOx. See also NITRO COMPOUNDS.
Hazard Codes:
F: Flammable 
Xi: Irritant 
Risk Statements about 1-Nitroguanidine (CAS NO.556-88-7):
R5 Heating may cause an explosion. 
R11 Highly flammable.  
R36/37/38 Irritating to eyes, respiratory system and skin.  
Safety Statements about α-Nitroguanidine (CAS NO.556-88-7):
S16 Keep away from sources of ignition - No smoking.  
S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.  
S37/39 Wear suitable gloves and eye/face protection.  
S47 Keep at temperature not exceeding ...°C (to be specified by the manufacturer).

【PackingGroup 】
I
【Cleanup Methods】
PROCESS PARAMETERS HAVE BEEN DEVELOPED WHICH PERMIT PURIFICATION OF WASTEWATERS CONTAINING DISSOLVED EXPLOSIVES BY TREATING THE WASTEWATER WITH SURFACTANT OF THE QUATERNARY AMINE TYPE AT PH OF APPROX 11.5. NITROGUANIDINE IS UNAFFECTED BY THE SURFACTANT TREATMENT, BUT CAN BE DESTROYED BY CONTACT WITH ION EXCHANGE RESIN. A METHOD OF ANALYSIS IS DESCRIBED.
STUDIES WERE CONDUCTED TO DETERMINE DECOMP RATE OF NITROGUANIDINE BY USE OF SODIUM SULFIDE & SODIUM HYDROXIDE. SODIUM HYDROXIDE WAS USED TO ADJUST PH ABOVE 11.0 & TO INCR SULFIDE REACTION RATE. THESE STUDIES SHOWED THAT NITROGUANIDINE CANNOT BE EFFECTIVELY DECOMPOSED WITH SODIUM HYDROXIDE ALONE; HOWEVER, IT WAS EFFECTIVE IN COMBINATION WITH SODIUM SULFIDE & THE NITROGUANIDINE DECOMPOSITION RATE WAS A FUNCTION OF THE SULFIDE CONCN ADDED. ALTHOUGH SUCCESSFUL, USE OF RELATIVELY LARGE AMT OF SULFIDE IS UNDESIRABLE.
【Transport】
UN 1336
【Fire Potential】
A very dangerous fire hazard when exposed to heat, flame, or by chemical reaction with oxidizers.
【Formulations/Preparations】
It is normally mixed with colloided nitrocellulose or ammonium nitrate and paraffin wax.
【DOT Emergency Guidelines】
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Fire or Explosion: Flammable/combustible material. May be ignited by heat, sparks or flames. DRIED OUT material may explode if exposed to heat, flame, friction or shock; treat as an explosive (GUIDE 112). Keep material wet with water or treat as an explosive (Guide 112). Runoff to sewer may create fire or explosion hazard. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Health: Some are toxic and may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Public Safety: CALL Emergency Response Telephone Number. ... Isolate spill or leak area immediately for at least 100 meters (330 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Ventilate closed spaces before entering. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Evacuation: Large spill: Consider initial evacuation for 500 meters (1/3 mile) in all directions. Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Fire: Cargo fires: DO NOT fight fire when fire reaches cargo! Cargo may EXPLODE! Stop all traffic and clear the area for at least 800 meters (1/2 mile) in all directions and let burn. Do not move cargo or vehicle if cargo has been exposed to heat. Tire or vehicle fires: Use plenty of water - FLOOD it! If water is not available, use CO2, dry chemical or dirt. If possible, and WITHOUT RISK, use unmanned hose holders or monitor nozzles from maximum distance to prevent fire from spreading to cargo area. Pay special attention to tire fires as re-ignition may occur. Stand by with extinguisher ready. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Small spills: Flush area with flooding quantities of water. Large spills: Wet down with water and dike for later disposal. KEEP "WETTED" PRODUCT WET BY SLOWLY ADDING FLOODING QUANTITIES OF WATER. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Nitroguanidine (Picrite), wetted with not less than 20% water; Nitroguanidine, wetted with not less than 20% water; Picrite, wetted/
【Reactivities and Incompatibilities】
Can react vigorously with oxidizing materials and the derivatives can be explosive.
Can react vigorously with oxidizing materials and the derivatives can be explosive.
【Specification】

 Attention:
1. Storage: Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
2. Handling: Avoid contact with heat, sparks and flame. Avoid ingestion and inhalation. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.

【Octanol/Water Partition Coefficient】
log Kow= -0.89
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
NITROGUANIDINE REMOVED FROM WASTEWATERS & SOLID WASTE PROPELLANTS & EXPLOSIVES FROM MFR OF MILITARY WEAPONS WAS DISPOSED OF IN SEVERAL DIFFERENT WAYS.
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

... By the action of concn sulfuric acid (H2SO4) on guanidine nitrate ...
... By the nitration of guanidine sulfate with fuming nitric acid (HNO3) ... /beta/
/Beta form/ is converted into the alpha-form by dissolving in concn sulfuric acid (H2SO4) and pouring into ice water ... /beta/
(alpha) Results when guanidine nitrate is dissolved in concentrated sulfuric acid and the solution is poured into water. (beta) Nitration of a mixture of guanidine sulfate and ammonium sulfate that results from the hydrolysis of dicyanadiamide by sulfuric acid.
Guanidine nitrate (dehydration)
【Usage】
Explosive.

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
(14)C labeled nitroguanidine was administered to Sprague-Dawley rats intravenously at a dose of 20 mg/kg, by gastric intubation at a dose of 20 mg/kg, and by oral intubation at a dose of 200 mg/kg. Blood samples were collected at times from 5 minutes to 24 hours post dosing, and urine samples were collected at approximately 4, 8, 24, 32, and 48 hours after drug administration. The animals were sacrificed at 48 hours post treatment, and liver, heart, lung, kidney, spleen, brain, testes, ovaries, and muscle were analyzed for (14)C activity. The administered label was rapidly excreted in the urine regardless of the route of dosing. Approximately 50 percent of the label was present in the urine at 4 hours post dosing, and approximately 95 percent was excreted by 24 hours. [Ho R et al; fundamental and Applied Toxicology 10 (3): 453-8 (1988)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
The rate constant for the vapor-phase reaction of 1-nitroguanidine with photochemically-produced hydroxyl radicals has been estimated as 21X10-12 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 18 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Nitroguanidine in aqueous solutions was photolyzed by UV light and sunlight to form guanidine nitrite, cyanoguanidine, ammonia, and nitrate; 1-nitroguanidine in natural surface water was photolyzed to form nitrite and hydroxyguanidine(4).

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