7-bromo-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,6,9-tetraen-5-amine Chemical Properties

Melting point:

350°C(lit.)

Boiling point:

287.4±50.0 °C(Predicted)

Density 

2.54±0.1 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

10.32±0.20(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C5H4BrN5/c6-3-2-4(7)8-1-9-5(2)11-10-3/h1H,(H3,7,8,9,10,11)

InChIKey

GZQVGSRUUTUJNG-UHFFFAOYSA-N

SMILES

C1=NC(N)=C2C(Br)=NNC2=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

7-bromo-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,6,9-tetraen-5-amine Usage And Synthesis

Chemical Properties

Yellow solid

Synthesis

The general procedure for the synthesis of 3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine using 4-aminopyrazolo[3,4-d]pyrimidine as starting material was as follows: 1H-pyrazolo[3,4-d]pyrimidin-4-amine (20.0 g, 148.0 mmol) and N-bromosuccinimide (27.7 g, 155.4 mmol) were suspended in N,N- dimethylformamide (DMF, 400 mL). The reaction mixture was heated to 80 °C and the reaction was stirred at this temperature for 2.5 hours. Upon completion of the reaction, the mixture was cooled to room temperature, followed by slow dropwise addition of water (800 mL) to quench the reaction. The resulting precipitate was collected by filtration and suspended in saturated sodium sulfite solution (100 mL). The solid product was filtered again and washed sequentially with water (3 x 100 mL) and cold ethanol (2 x 50 mL). Finally, the product was dried under vacuum to afford 3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine as a beige solid (22.7 g, 105.9 mmol, 72% yield).

References

[1] Patent: WO2017/17619, 2017, A1. Location in patent: Page/Page column 8-9
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 17, p. 4774 - 4786
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1982, vol. 18, # 7, p. 753 - 755
[4] Khimiya Geterotsiklicheskikh Soedinenii, 1982, # 7, p. 982 - 984
[5] Patent: EP2548877, 2013, A1. Location in patent: Paragraph 0416