3-Nitro-1,2,4-triazole Chemical Properties

Melting point:

210 °C (dec.)(lit.)

Boiling point:

213.51°C (rough estimate)

Density 

1.7897 (rough estimate)

refractive index 

1.4164 (estimate)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Methanol

form 

Solid

pka

5.92±0.20(Predicted)

color 

Light Yellow

Water Solubility 

slightly soluble

BRN 

607167

InChI

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

InChIKey

KUEFXPHXHHANKS-UHFFFAOYSA-N

SMILES

N1C([N+]([O-])=O)=NC=N1

CAS DataBase Reference

24807-55-4(CAS DataBase Reference)

NIST Chemistry Reference

1H-1,2,4-triazole, 3-nitro-(24807-55-4)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

22-24/25-36-26

WGK Germany 

3

F 

9

HazardClass 

IRRITANT

HS Code 

29339990

MSDS

• Language:English Provider:3-Nitro-1,2,4-triazole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Nitro-1,2,4-triazole Usage And Synthesis

Chemical Properties

Light Yellow Solid

Uses

3-Nitro-1,2,4-triazole is used in oligonucleotide synthesis. Also a radiosensitizer of hypoxic cells in vitro.

Synthesis

General procedure for the synthesis of 3-nitro-1,2,4-triazole from 1H-1,2,4-triazol-5-amine: In a fume hood, 3-amino-1,2,4-triazole (26.3 g, 0.297 mol) was added to an aqueous solution of sodium nitrite (100.0 g, 1.45 mol, dissolved in 150 ml of water) fitted with an overhead mechanical stirrer and a 100 ml homogeneous pressure dosing funnel in a 2.0 liter three-necked round-bottomed flask. The suspension was cooled in an ice water bath and the mechanical stirrer was activated. After stirring for 10 minutes, concentrated nitric acid (85 ml) was slowly added dropwise through the dosing funnel for a controlled period of 2.5-3.0 hours (note the foaming phenomenon). After the dropwise addition was completed, the ice water bath was removed and the yellow suspension was continued to be stirred at room temperature for 1 hr until the foaming stopped. The crude product was collected by filtration and the yellow solid cake was dried overnight under vacuum with an oil pump to give 47 g of product. The crude product was dissolved in boiling methanol (300 ml) for 30 min, followed by room vacuum filtration. The filtrate was cooled to room temperature and placed in a refrigerator at -15°C overnight to crystallize 3-nitro-1,2,4-triazole as a light yellow solid. The crystallized product was washed with cold methanol and dried overnight at a pressure of 1.9 mmHg to give 21-23 g (62%-68% yield) of 3-nitro-1,2,4-triazole with a melting point of 208°C-211°C (literature values 208°C-210°C). The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 8.86 (s, 1H); 13C NMR (75 MHz, DMSO-d6): δ 163.1,146.3; IR (solid): 3162,2861,2776,2730 cm-1. The purity of the product was determined to be 97% by RP-HPLC with retention time tR=2.01 min (detection wavelength 254 nm).

References

[1] Organic Process Research and Development, 2014, vol. 18, # 7, p. 886 - 890
[2] Tetrahedron, 1980, vol. 36, # 20-21, p. 3075 - 3085
[3] Organic Preparations and Procedures International, 2014, vol. 46, # 3, p. 267 - 271
[4] Russian Journal of Organic Chemistry, 2014, vol. 50, # 5, p. 742 - 746
[5] Zh. Org. Khim., 2014, vol. 50, # 5, p. 752 - 756,5

3-Nitro-1,2,4-triazole(24807-55-4)Related Product Information

• Ribavirin
• 1H-Benzotriazole
• 5-Methyl-1H-benzotriazole
• 1,2,3-1H-Triazole
• 1,2,4-Triazole
• NITROGEN DIOXIDE
• 1-(MESITYLENE-2-SULFONYL)-3-NITRO-1,2,4-TRIAZOLE
• 1-(p-Toluenesulfonyl)-3-nitro-1,2,4-triazole
• 5-NITRO-1H-[1,2,4]TRIAZOLE-3-CARBOXYLIC ACID
• 1,2,4-TRIAZOLE
• 1-(2,4,6-TRIISOPROPYLBENZENESULFONYL)-3-NITRO-1,2,4-TRIAZOLE,TSNT 1-(2,4,6-Tri-isopropylbenzenesulfonyl)-3-nitro-1,2,4-triazole
• 1-(3-NITRO-1H-1,2,4-TRIAZOL-1-YL)ACETONE
• AK 2123
• 3-BROMO-5-NITRO-1,2,4-TRIAZOLE,5-BROMO-3-NITRO-1 2 4-TRIAZOLE 98%
• 1-CARBOXYMETHYL-3-NITRO-1,2,4-TRIAZOLE
• 5-Amino-3-nitro-1,2,4-triazole
• 1H-4-Amino-5-nitro-1,2,3-triazole
• 1-methyl-3-nitro-1,2,4-triazole