4,5-DIBROMO-1H-1,2,3-TRIAZOLE Chemical Properties

Melting point:

194 °C (decomp)

Boiling point:

47,3 C

Density 

2.18 g/cm

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

5.22±0.70(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C2HBr2N3/c3-1-2(4)6-7-5-1/h(H,5,6,7)

InChIKey

GUQUYKTWVBJKFL-UHFFFAOYSA-N

SMILES

N1C(Br)=C(Br)N=N1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

2933.99.8290

HazardClass 

IRRITANT

4,5-DIBROMO-1H-1,2,3-TRIAZOLE Usage And Synthesis

Uses

4,5-Dibromo-1H-1,2,3-triazole is an intermediate used in preparation of isoxazole derivative herbicides.

Synthesis

Example 120: Preparation of 4,5-dibromo-1H-1,2,3-triazole. Bromine (1.5 mL, 29 mmol) was slowly added to a solution of 1H-[1,2,3]triazole (1.26 mL, 21.7 mmol) in water (10 mL) at 5 °C. The reaction mixture was stirred at 5°C for 1.5 h. The white solid (2.375 g) was isolated by filtration and washed with cold water (5 mL). Bromine (1.5 mL, 29 mmol) was added again to the combined filtrates. The mixture was stirred at room temperature for 20 h. More white solid (1.83 g) was separated by filtration and washed with cold water (5 mL). Bromine (1.5 mL, 29 mmol) was added a third time to the combined filtrates. The reaction mixture was stirred at room temperature for 20 h. Additional white solid (375 mg) was isolated by filtration and washed with cold water (5 mL). All white solids were combined and dried to give 4,5-dibromo-1H-[1,2,3]- triazole (4.92 g, 93% yield). Melting point: 194.7°C.

References

[1] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 12, p. 1341 - 1347
[2] Patent: WO2007/96576, 2007, A1. Location in patent: Example I20
[3] Patent: WO2017/80980, 2017, A1. Location in patent: Page/Page column 68-69
[4] Justus Liebigs Annalen der Chemie, 1947, vol. 558, p. 34,41
[5] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 13, p. 1535 - 1543

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