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22300-52-3

22300-52-3 Structure

22300-52-3 Structure
IdentificationBack Directory
[Name]

4,5-Dibromo-2H-1,2,3-triazole
[CAS]

22300-52-3
[Synonyms]

2H-1,2,3-Triazole, 4,5-dibromo-
[EINECS(EC#)]

200-110-4
[Molecular Formula]

C2HBr2N3
[MDL Number]

MFCD19440717
[MOL File]

22300-52-3.mol
[Molecular Weight]

226.86
Chemical PropertiesBack Directory
[Boiling point ]

347.5±22.0 °C(Predicted)
[density ]

2.620
[storage temp. ]

Inert atmosphere,2-8°C
[pka]

5.22±0.70(Predicted)
[Appearance]

Off-white to light yellow Solid
[InChI]

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

GUQUYKTWVBJKFL-UHFFFAOYSA-N
[SMILES]

N1=C(Br)C(Br)=NN1
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H332-H335
[Precautionary statements ]

P280-P305+P351+P338-P310
Hazard InformationBack Directory
[Uses]

4,5-Dibromo-2H-triazole was a useful reagent in discovery of selective small molecular inhibitors of monoacylglycerol acyltransferase 3.
[Synthesis]

1,2,3-1H-Triazole

288-36-8

4,5-Dibromo-2H-1,2,3-triazole

22300-52-3

To a 3000 mL three-necked round-bottomed flask was added 2H-1,2,3-triazole (100 g, 1.45 mol, 1.00 eq.) and water (1000 mL), followed by the slow addition of bromine (Br2, 522 g, 3.27 mol, 2.25 eq.). The reaction mixture was placed in a 50 °C oil bath and the reaction was stirred overnight. Upon completion of the reaction, the reaction was quenched by the slow addition of 1000 mL of aqueous sodium sulfite (Na2SO3). The reaction mixture was separated by filtration and the solid product was collected. The resulting solid was dried in an oven under reduced pressure to give 4,5-dibromo-2H-1,2,3-triazole (313 g, 95% yield) as a white solid.

[References]

[1] Organic Letters, 2010, vol. 12, # 20, p. 4632 - 4635
[2] Patent: US2017/166584, 2017, A1. Location in patent: Paragraph 0718; 0719
[3] Patent: WO2012/151512, 2012, A2. Location in patent: Page/Page column 151
[4] Patent: WO2015/74064, 2015, A2. Location in patent: Paragraph 0260
[5] Patent: WO2018/111803, 2018, A1. Location in patent: Page/Page column 24
Spectrum DetailBack Directory
[Spectrum Detail]

4,5-Dibromo-2H-1,2,3-triazole(22300-52-3)1HNMR
4,5-Dibromo-2H-1,2,3-triazole(22300-52-3)13CNMR
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