932-64-9

Basic information

• Product Name: 1,2-dihydro-5-nitro-3H-1,2,4-triazol-3-one
• Synonyms: 1,2-dihydro-5-nitro-3H-1,2,4-triazol-3-one;3-Nitro-1,2,4-triazol-5-one.;5-nitro-1,2,4-triazol-3-one;5-nitro-1,2-dihydro-1,2,4-triazol-3-one;nitrotriazolone;2,3-Dihydro-5-nitro-1H-1,2,4-triazol-3-one;3-Nitro-1H-1,2,4-triazole-5-ol;3-Nitro-4,5-dihydro-1H-1,2,4-triazole-5-one
• CAS NO: 932-64-9
• Molecular Formula: C₂H₂N₄O₃
• Molecular Weight: 130.06228
• EINECS: 213-254-4
• Mol File: 932-64-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 240.69°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 2.46g/cm³
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.4164 (estimate)
• Solubility: 16.8g/L in organic solvents at 20 ℃
• PKA: 3.76[at 20 ℃]
• Water Solubility: 17.2g/L at 25℃
• CAS DataBase Reference: 1,2-dihydro-5-nitro-3H-1,2,4-triazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dihydro-5-nitro-3H-1,2,4-triazol-3-one(932-64-9)
• EPA Substance Registry System: 1,2-dihydro-5-nitro-3H-1,2,4-triazol-3-one(932-64-9)

Safety Data

• RIDADR: 0490
• HazardClass: 1.1D
• Hazardous Substances Data: 932-64-9(Hazardous Substances Data)

Usage

General Description

A solid or liquid. May explode under prolonged exposure to heat or fire. Primary hazard is blast of an instantaneous explosion, not flying projectiles or fragments.

Reactivity Profile

The triazoles are a group of highly explosive materials that are sensitive to heat, friction, and impact. Sensitivity varies with the type substitution to the triazole ring. Metal chelated and halogen substitution of the triazol ring make for a particularly heat sensitive material. Azido and nitro derivatives have been employed as high explosives. No matter the derivative these materials should be treated as explosives.

Safety Profile

Low toxicity by ingestion and skin contact. A skin and eye irritant. An unstable explosive. When heated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C2H2N4O3/c7-2-3-1(4-5-2)6(8)9/h(H2,3,4,5,7)

Synthetic route

2,4-dihydro-1,2,4-triazol-3-one (930-33-6) → 3-nitro-1,2,4-triazol-5-one (932-64-9)

Conditions	Yield
With sulfuric acid; nitric acid In water at 65℃; for 2h;	96%
With nitric acid at 50 - 85℃; for 0.5h;	84%
With nitric acid at 54.9 - 59.9℃;
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid In water at 65℃; for 2h;

1-nitro-4,5-dihydro-1H-1,2,4-triazol-5-one → 3-nitro-1,2,4-triazol-5-one (932-64-9)

Conditions	Yield
With sulfuric acid

methyl ethynyl ketone (1423-60-5) + 3-nitro-1,2,4-triazol-5-one (932-64-9) + triphenylphosphine (603-35-0) → 2-(5-nitro-2,4H-1,2,4-triazol-4-yl-2-ylid)-1-methyl-3-triphenylphosphoniopropanone

Conditions	Yield
In dichloromethane at 20℃; for 5h;	98%

propynoic acid methyl ester (922-67-8) + 3-nitro-1,2,4-triazol-5-one (932-64-9) + triphenylphosphine (603-35-0) → methyl 2-(5-nitro-2,4H-1,2,4-triazol-4-yl-2-ylid)-1-methyl-3-triphenylphosphoniopropionate

Conditions	Yield
In dichloromethane at 20℃; for 5h;	98%

3-nitro-1,2,4-triazol-5-one (932-64-9) + triphenylphosphine (603-35-0) + propynoic acid ethyl ester (623-47-2) → ethyl 2-(5-nitro-2,4H-1,2,4-triazol-4-yl-2-ylid)-1-methyl-3-triphenylphosphoniopropionate

Conditions	Yield
In dichloromethane at 20℃; for 5h;	95%

5-amino-3-(3,4-diamino-1,2,4-triazol-5-yl)-1H-1,2,4-triazole + 3-nitro-1,2,4-triazol-5-one (932-64-9) → C4H7N9*C2H2N4O3

Conditions	Yield
In water for 0.5h; Reflux;	90%

3,6-diamino-1H-[1,2,4]triazolo[4,3-b][1,2,4]triazole (400063-96-9) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 3,6-diamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazol-2-ium 3-nitro-5-oxo-1,2,4-triazolate

Conditions	Yield
In water at 50℃; for 4h;	89%

oxalic acid hydrazide (996-98-5) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → C2H2N4O3*C2H6N4O2

Conditions	Yield
In water at 80℃; for 2h;	88%

3-nitro-1,2,4-triazol-5-one (932-64-9) → 3-chloro-1,2,4-triazol-5(1H,4H)-one (1003-34-5)

Conditions	Yield
With hydrogenchloride for 7h; Substitution; Heating;	85.7%

formaldehyd (50-00-0) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 2-Hydroxymethyl-5-nitro-2,4-dihydro-[1,2,4]triazol-3-one (78663-78-2)

Conditions	Yield
In water; acetone for 8h; Ambient temperature;	85%

1-adamanthanol (768-95-6) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 1,4-di(1-adamantyl)-3-nitro-1,2,4-triazol-5(1H,4H)-one

Conditions	Yield
With sulfuric acid In water at 20℃; for 24h;	85%

(E)-1,2-bis(3,4-diamino-1,2,4-triazol-5-yl)-ethene (1338484-47-1) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 1,1′-(ethane-5-yl)bis(3,4-diamino-1,2,4-triazolium) di(3-nitro-1,2,4-triazolate-5-one)

Conditions	Yield
In water at 60 - 100℃; for 1h;	84.6%

3,6,7-triamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazolium (13728-15-9) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → C3H6N8*C2H2N4O3

Conditions	Yield
In water at 80 - 120℃;	83.7%

3-nitro-1,2,4-triazol-5-one (932-64-9) → C4H4N8O3 (960607-22-1)

Conditions	Yield
With sulfuric acid In water at 5 - 10℃; for 7h; Electrolysis;	82%

3-nitro-1,2,4-triazol-5-one (932-64-9) → 5-amino-2,4-dihydro-3H-1,2,4-triazol-3-one (1003-35-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 1551.44 Torr; for 5h; Reduction;	70%

2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (52162-55-7, 69256-45-7, 61826-14-0) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 5-nitro-2-(4-p-tolyloxy-5-p-tolyloxymethyl-tetrahydro-furan-2-yl)-2,4-dihydro-[1,2,4]triazol-3-one

Conditions	Yield
With sodium hydride In acetonitrile	67%

1-adamanthanol (768-95-6) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 1-(1-adamantyl)-3-nitro-1,2,4-triazol-5(1H,4H)-one

Conditions	Yield
With sulfuric acid In water at 20℃; for 1h;	64%

N-(hydroxymethyl)acetamide (625-51-4) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 1-acetamidomethyl-3-nitro-1,2,4-triazol-5-one (78663-80-6)

Conditions	Yield
In ethanol Ambient temperature; 1.)8 h 2.)overnight;	53%

4H-1,2,4-triazol-3-amine (61-82-5) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → C2H2N4O3*C2H4N4 (143984-00-3)

Conditions	Yield
In ethanol at 20℃; for 2h;	43.2%

3-nitro-1,2,4-triazol-5-one (932-64-9) → C4H4N8O2 (1352233-46-5) + C4H4N8O3 (960607-22-1) + 5-amino-2,4-dihydro-3H-1,2,4-triazol-3-one (1003-35-6)

Conditions	Yield
With sodium sulfate In water pH=2 - 7; Electrolysis;	A n/a B n/a C 39%
With sulfuric acid In water at 20℃; Electrolysis;	A n/a B n/a C 14%

picryl fluoride (364-44-3) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 5-nitro-2-picryl-2,4-dihydro-3H-1,2,4-triazol-3-one-4-15N (128455-79-8) + 5-nitro-2,4-dipicryl-2,4-dihydro-3H-1,2,4-triazol-3-one-4-15N (128455-80-1)

Conditions	Yield
In various solvent(s) for 16h; Ambient temperature;	A 34% B 26%

picryl fluoride (364-44-3) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 5-nitro-2,4-dipicryl-2,4-dihydro-3H-1,2,4-triazol-3-one (128455-78-7) + 5-nitro-2-picryl-2,4-dihydro-3H-1,2,4-triazol-3-one (66652-96-8)

Conditions	Yield
In various solvent(s) for 16h; Ambient temperature;	A 30% B 34%

N-methyl-N-chloromethyl-N-nitroamine (13126-14-2) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 2,4-bis(2-nitrazaprop-1-yl)-3-nitro-1,2,4-triazol-5-one

Conditions	Yield
Stage #1: 3-nitro-1,2,4-triazol-5-one With triethylamine In acetone for 0.0833333h; Stage #2: N-methyl-N-chloromethyl-N-nitroamine In acetone at 20℃; for 12h;	33%

methyl vinyl ketone (78-94-4) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 5-Nitro-2,4-bis-(3-oxo-butyl)-2,4-dihydro-[1,2,4]triazol-3-one (78663-76-0)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 80℃; for 8h; Yield given;

3-nitro-1,2,4-triazol-5-one (932-64-9) + dimethyl sulfate (77-78-1) → 4-methyl-3-nitro-1,2,4-triazol-5(1H,4H)-one (22244-54-8) + 1-methyl-3-nitro-1,2,4-triazol-5(1H,4H)-one (22244-55-9) + 3-nitro-5-methoxy-1,2,4-triazole (72285-34-8)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 18 - 20℃; for 8h; Product distribution; other solvent - water; var. ratio of reagents;	A 54 % Spectr. B 30 % Spectr. C 16 % Spectr.

1-amino-2-azidoethane (87156-40-9) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → 2-azidoethylammonium 3-nitro-1,2,4-triazol-5-onate

Conditions	Yield
In water Ambient temperature;

cadmium(II) carbonate (739319-89-2) + 3-nitro-1,2,4-triazol-5-one (932-64-9) → Cd(H2O)6(2+)*Cd(C2HN4O3)4(2-)*4H2O=[Cd(C2HN4O3)4Cd(H2O)6]*4H2O

Conditions	Yield
In water byproducts: CO2; stirring soln. of ligand, addn. of excess of Cd-salt (60°C), stirring (60°C, 30 min, pptn.); hot filtration, dissolving (EtOH), sepn. of CdCO3, standing (6 h, pptn.), recrystn. (H2O, 25°C);

lead(II) nitrate + 3-nitro-1,2,4-triazol-5-one (932-64-9) → Pb(2+)*2C2HN4O3(1-)*H2O=Pb(C2HN4O3)2*H2O

Conditions	Yield
With NaOH In water addn. of soln. of hydroxide to soln. of ligand, stirring (60°C, pH = 6 - 7), dropping this soln. to soln. of Pb-salt (60°C), stirring, heating (60°C, 30 min, pptn.); recrystn. (H2O, 25°C);

Upstream product

• 930-33-6 2,4-dihydro-1,2,4-triazol-3-one 

Downstream Products

• 128455-79-8 5-nitro-2-picryl-2,4-dihydro-3H-1,2,4-triazol-3-one-4-¹⁵N 
• 128455-80-1 5-nitro-2,4-dipicryl-2,4-dihydro-3H-1,2,4-triazol-3-one-4-¹⁵N 
• 128455-78-7 5-nitro-2,4-dipicryl-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 66652-96-8 5-nitro-2-picryl-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 22244-54-8 4-methyl-3-nitro-1,2,4-triazol-5(1H,4H)-one 
• 22244-55-9 1-methyl-3-nitro-1,2,4-triazol-5-one 
• 72285-34-8 3-nitro-5-methoxy-1,2,4-triazole 
• 1352233-46-5 C₄H₄N₈O₂ 
• 1003-35-6 5-amino-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 1352233-45-4 C₄H₆N₈O₂ 
• 960607-22-1 C₄H₄N₈O₃ 
• 1003-34-5 3-chloro-1,2,4-triazol-5(1H,4H)-one 

Relevant articles and documents

The enthalpies of formation of 1,2,4-triazol-5-one and 3-nitro-1,2,4-triazol-5-one

The standard (p = 0.1 MPa) molar enthalpies of formation of 1,2,4-triazol-5-one and 3-nitro-1,2,4-triazol-5-one have been determined from measurements of their energies of combustion in oxygen as -(142.4 +/- 0.7) kJ*mol-1 and -(129.4 +/- 1.1) kJ*mol-1, respectively.From measurements of the enthalpies of neutralization of 3-nitro-1,2,4-triazol-5-one with NaOH(aq) and KOH(aq) the enthalpies of formation of the crystalline sodium and potassium salts have been determined as -(362.6 +/- 1.2) kJ*mol-1 and -(385.1+/-1.1) kJ*mol-1, respectively.

METHOD FOR OBTAINING SOLUTIONS OF OTA IN A CONCENTRATED SULFURIC ACID MEDIUM； SAID SOLUTIONS； AND METHOD FOR PREPARING ONTA

A method for obtaining solutions that contain 1,2,4-triazole-5-one (OTA) in concentrated sulphuric acid, includes using 3-amino-1,2,4-triazole (ATA) as a precursor of OTA. There is also provided a method for preparing 3-nitro-1,2,4-triazole-5-one (4) (ONTA) from the solutions.

Synthesis and thermal decomposition of 15N-labelled NTO

5-Nitro-2,4-dihydro-3H-1,2,4-triazol-3-one (NTO) has been synthesized in good yield with 15N at the 1 and 2 positions. The N-H coupling provides unequivocal assignments for 1H and 15N NMR spectra and the acidic proton. The products of thermal decomposition at 270 °C were identified spectroscopically. NMR spectra reveal that thermal decomposition results in the formation of 2,4-dihydro-3H-1,2,4-triazol-3-one and ammonia (the latter observed as ammonium ion). The production of ammonia from the thermal decomposition of an energetic material is unprecedented. The gas products HCN, 15N14N, 15N2 and CO were detected by mass spectrometry. Some possible mechanisms of thermal decomposition are discussed.