24807-55-4

Basic information

• Product Name: 3-Nitro-1,2,4-triazole
• Synonyms: s-Triazole, 3-nitro-;AKOS MSC-0736;AKOS B006601;3-NITRO-1H-1,2,4-TRIAZOLE;3-NITRO-1,2,4-TRIAZOLE;5-NITRO-1H-[1,2,4]TRIAZOLE;1H-1,2,4-Triazole, 3-nitro-;1H-1,2,4-Triazole,3-nitro-(9CI)
• CAS NO: 24807-55-4
• Molecular Formula: C₂H₂N₄O₂
• Molecular Weight: 114.06
• EINECS: 246-468-1
• Product Categories: NITRO;FINE Chemical & INTERMEDIATES;Nucleotides and Nucleosides;Biochemistry;Condensation & Active Esterification;Condensing Agents (DNA / RNA Synthesis);Nucleosides, Nucleotides & Related Reagents;Protecting Agents, Phosphorylating Agents & Condensing Agents;Synthetic Organic Chemistry;Bases & Related Reagents;Nucleotides;Building Blocks;Heterocyclic Building Blocks;Triazoles;Heterocycles
• Mol File: 24807-55-4.mol

Chemical Properties

• Melting Point: 210 °C (dec.)(lit.)
• Boiling Point: 213.51°C (rough estimate)
• Flash Point: 201.4 °C
• Appearance: White or light yellow powder
• Density: 1.7897 (rough estimate)
• Vapor Pressure: 6.54E-07mmHg at 25°C
• Refractive Index: 1.4164 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Methanol
• PKA: 5.92±0.20(Predicted)
• Water Solubility: slightly soluble
• BRN: 607167
• CAS DataBase Reference: 3-Nitro-1,2,4-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nitro-1,2,4-triazole(24807-55-4)
• EPA Substance Registry System: 3-Nitro-1,2,4-triazole(24807-55-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• F: 9
• HazardClass: IRRITANT
• Hazardous Substances Data: 24807-55-4(Hazardous Substances Data)

Usage

Uses

Used in Oligonucleotide Synthesis:
3-Nitro-1,2,4-triazole is utilized as a synthetic building block in the creation of oligonucleotides, which are short sequences of nucleic acids. These oligonucleotides have significant applications in molecular biology, genetic research, and the development of new therapeutic strategies.
Used in Radiosensitization:
In the field of radiotherapy, 3-Nitro-1,2,4-triazole serves as a radiosensitizer, specifically for hypoxic cells in vitro. Radiosensitizers are compounds that enhance the sensitivity of cells to the effects of ionizing radiation, thereby improving the effectiveness of radiation treatments for cancer. By increasing the radiosensitivity of hypoxic cells, 3-Nitro-1,2,4-triazole contributes to the overall success of radiation therapy in targeting cancerous cells.

InChI:InChI=1/C2H2N4O2/c7-6(8)2-3-1-4-5-2/h1H,(H,3,4,5)

Upstream product

• 61-82-5 3⁽⁵⁾-amino-1,2,4-triazole 
• 36899-13-5 potassium salt of 3-nitro-1,2,4-triazole 
• 74205-83-7 (3-nitro-1H-1,2,4-triazol-1-yl)methanol 
• 81911-06-0 C₅H₄N₈O₄ 
• 81606-82-8 (3-Nitro-[1,2,4]triazol-1-yl)-acetonitrile 
• 70965-24-1 ethyl 2-(3-nitro-1H-1,2,4-triazol-1-yl)acetate 
• 26621-45-4 methyl-3-nitro-1H-1,2,4-triazole 
• 71-43-2 benzene 
• 126401-88-5 C₁₆H₃₆N⁽¹⁺⁾*C₂HN₄O₂^(1-) 
• 133157-99-0 1-Chloro-3-nitro-1,2,4-triazole 
• 61-82-5 3-amino-1,2,4-triazole 
• 7664-93-9 sulfuric acid 

Downstream Products

• 147917-48-4 1-(1-adamantyl)-3-nitro-1H-1,2,4-triazole 
• 60728-92-9 3-nitro-1,2,4-triazol-1-ylbutan-3-one 
• 70965-24-1 ethyl 2-(3-nitro-1H-1,2,4-triazol-1-yl)acetate 
• 70965-23-0 methyl 2-(3-nitro-[1,2,4]triazol-1-yl)acetate 
• 1027314-27-7 Benzoic acid (2S,4S,5R)-4-fluoro-5-[4-(3-nitro-[1,2,4]triazol-1-yl)-2-oxo-2H-pyrimidin-1-yl]-tetrahydro-furan-2-ylmethyl ester 
• 6818-99-1 3-chloro-1H-1,2,4-triazole 
• 161834-99-7 6-(3-nitro-1,2,4-triazol-1-yl)-9-<3',5'-di-O-benzoyl-2'-O-(tetrahydropyran-2-yl)-β-D-ribofuranosyl>-9H-purine 
• 70890-46-9 3-nitro-5-(3-nitro-1,2,4-triazol-1-yl)-1,2,4-triazol 
• 105958-58-5 methyl 3-(3-nitro-1H-1,2,4-triazol-1-yl)propanoate 
• 26621-29-4 1-methyl-5-nitro-1H-1,2,4-triazole 

Relevant articles and documents

Synthesis and structure of new ditopic ligands containing tetrazole and 3-nitro-1,2,4-triazole fragments

Alkylation of 3-nitro-1,2,4-triazole with haloalkyltetrazoles has afforded in high yields previously unknown 1-[2-(3-nitro-1H-1,2,4-triazol-1-yl)ethyl]-1H- tetrazole and 2-tert-butyl-5-(3-nitro-1H-1,2,4-triazol-1-ylmethyl)-2H-tetrazole. The molecular and crystal structure of these compounds has been established by X-ray diffraction analysis (XRD).

A green and facile approach for synthesis of nitro heteroaromatics in water

A convenient and green method for the oxidation of nitrogen-rich heterocyclic amines to nitro-substituted heteroaromatics using potassium peroxymonosulfate (2KHSO5·KHSO4·K 2SO4, Oxone) in water was developed. This method has several advantages over previous methods: operational simplicity, safety, inexpensive reagents, the use of H2O as the sole solvent, and mild conditions. The utility of the present oxidative system was demonstrated by the synthesis of the important energetic compounds 3,4,5-trinitro-1H-pyrazole (TNP) and 5-amino-3-nitro-1H-1,2,4-triazole (ANTA).

Oxidation of Amino Derivatives of 1,2,4-Triazole

Derivatives of 3-nitro-5-R-1,2,4-triazoles are prepared by oxidation of the corresponding amino-compounds in the system 30% hydrogen peroxide - sodium tungstate. The activity of aminotriazoles decreases with increasing electronacceptor ability. For substrates unsubstituted at the heteroatom the process is promoted by bases. 3,5-Diamino-1,2,4-triazole is oxidized in two steps, and substantial difference in the rates of of the first and second stages of oxidation yielding respectively (5-amino-3-nitro- and 3,5-dinitro-1,2,4-triazole allows isolation of the former in up to 60% yield. N,N′-Azoxy-3,3′-bis(5-amino-1,2,4-triazole) is formed as a by-product. In 1-substituted 3,5-diaminotriazoles only one, peripheral, amino group is oxidized to afford derivatives of 5-amino-3-nitro-1,2,4-triazole.

OXIDATIVE ALKYLATION OF AZOLES. I. REACTION OF N-CHLORO-3-NITRO-TRIAZOLES WITH METHYL IODIDE

The reaction of methyl iodide with N-chloro-3-nitro-, and N-chloro-5-methyl-3-nitro-1,2,4-triazoles leads to the release of iodine and the formation of a mixture of compounds containing 3-nitro-1,2,4-triazoles unsubstituted at the nitrogen, the N-mono- and N,N-dimethylated derivatives (triazolium salts), and the products from their further transformations (1,4-dimethyl-5-triazolones).

5-nitro-2-(3,5-diamino-2,4,6-trinitrophenyl)-1,2,4-triazole, its preparation process and explosive material containing it

The invention relates to 5-nitro-2(3,5-diamino-2,4,6-trinitrophenyl)-1,2,4-triazole of formula: STR1 It is prepared by reacting a 1-halogeno-3,5-diamino-2,4,6-trinitrobenzene with 3-nitro-1,2,4-triazole or one of its alkali metal salts. This triazole derivative can be used as a secondary explosive. It has a lower shock sensitivity than octogen, while still being able to supply a high energy.

4,6-di-2-(5-nitro-1,2,4-triazole)-5-nitropyrimidine

The invention relates to a novel pyrimidine derivative. This derivative is 4,6-di-2-(5-nitro-1,2,4-triazole)-5-nitropyrimidine of formula: STR1 in the form of the pure isomer or mixtures of isomers. It can be prepared by reacting a dihalogeno nitropyrimidine with 5-nitro-1,2,4-triazole. It can be used as a secondary explosive.