| Identification | Back Directory | [Name]
4,5-DIBROMO-1H-1,2,3-TRIAZOLE | [CAS]
15294-81-2 | [Synonyms]
NSC222414
v-Triazole,4,5-dibroMo-
4,5-dibromo-2H-triazole
4,5-Dibrom-1H-1,2,3-triazole
v-Triazole,4,5-dibroMo- (8CI)
4,5-DIBROMO-1H-1,2,3-TRIAZOLE
4,5-dibromo-2H-1,2,3-triazole
1H-1,2,3-triazole, 4,5-dibromo- | [Molecular Formula]
C2HBr2N3 | [MDL Number]
MFCD08062401 | [MOL File]
15294-81-2.mol | [Molecular Weight]
226.86 |
| Chemical Properties | Back Directory | [Melting point ]
194 °C (decomp) | [Boiling point ]
47,3 C | [density ]
2.18 g/cm | [storage temp. ]
Inert atmosphere,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 |
| Hazard Information | Back Directory | [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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