6-BROMO[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE

6-BROMO[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE Property

Density 

2.13±0.1 g/cm3 (20 ºC 760 Torr)

storage temp. 

Sealed in dry,Room Temperature

pka

-0.60±0.30(Predicted)

form 

solid

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C5H3BrN4/c6-4-1-7-5-8-3-9-10(5)2-4/h1-3H

InChIKey

VEPBELSFCORKNT-UHFFFAOYSA-N

SMILES

C12=NC=NN1C=C(Br)C=N2

Safety

Hazard Codes 

Xn

Risk Statements 

22

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

6-BROMO[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 6-bromo-[1,2,4]triazolo[1,5-a]pyrimidines from 2-bromomalonaldehyde and 1H-1,2,4-triazol-5-amine: 3-amino-1H-1,2,4-triazole (6 mmol, 0.5 g) was dissolved in 5 mL of anhydrous acetic acid and slowly added dropwise at room temperature to a 2-bromomalonaldehyde (6 mmol, 0.9 g) in 5 mL of anhydrous acetic acid in suspension. The reaction mixture was heated to 80 °C and maintained for 7 hours. Upon completion of the reaction, the acetic acid was removed by evaporation under reduced pressure. Dichloromethane (DCM) was added to the residue, and the organic phase was washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure to yield 918 mg (78% yield) of 6-bromo-[1,2,4]triazolo[1,5-a]pyrimidine, which was of sufficient purity to meet the requirements for subsequent use.

References

[1] Patent: WO2011/15343, 2011, A1. Location in patent: Page/Page column 39-40
[2] Arkivoc, 2016, vol. 2016, # 5, p. 268 - 278