6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE Chemical Properties

Melting point:

151-153

Density 

1.89±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

2.38±0.50(Predicted)

form 

Solid

Appearance

Light yellow to green yellow Solid

InChI

InChI=1S/C6H4BrN3/c7-5-1-2-6-9-8-4-10(6)3-5/h1-4H

InChIKey

PFKZKSHKBBUZKU-UHFFFAOYSA-N

SMILES

C12=NN=CN1C=C(Br)C=C2

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

WGK Germany 

3

Hazard Note 

Harmful/Irritant/Keep Cold

HS Code 

2933998090

6-BROMO-1,2,4-TRIAZOLO[4,3-1]PYRIDINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 6-bromo-1,2,4-triazolo[4,3-1]pyridine from 2-hydrazino-5-bromopyridine and triethyl orthoformate: to a solution of 5-bromo-2-hydrazinopyridine (7.87 g, 42 mmol) in 200 mL of diethoxymethoxyethane was added p-toluenesulfonic acid (0.30 g, 1.7 mmol), the mixture was heated to 110 °C and stirred for 20 hours. After completion of the reaction, the mixture was cooled to room temperature and concentrated under vacuum. The residue was diluted with 150 mL of water, washed with saturated aqueous NaHCO3 (40 mL), and extracted with dichloromethane (300 mL × 3). The organic phases were combined, dried with anhydrous Na2SO4, and concentrated under vacuum. Purification of the residue by fast silica gel chromatography (petroleum ether/ethyl acetate, v/v = 2/1) afforded 6-bromo-1,2,4-triazolo[4,3-1]pyridine as a yellow solid (6.60 g, 79.77% yield). Mass spectrum (ESI, cation mode) m/z: 197.9 [M + H]+; 1H NMR (600 MHz, CDCl3): δ 8.82 (s, 1H), 8.34 (s, 1H), 7.75 (d, J = 9.7 Hz, 1H), 7.36 (d, J = 9.7 Hz, 1H).

References

[1] Patent: US2014/134133, 2014, A1. Location in patent: Paragraph 0451

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