3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine Chemical Properties

Melting point:

216-218℃

Boiling point:

533.7±60.0 °C(Predicted)

Density 

1.44

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

-4.09±0.31(Predicted)

color 

Red

InChI

InChI=1S/C12H14N8/c1-7-5-9(3)19(17-7)11-13-15-12(16-14-11)20-10(4)6-8(2)18-20/h5-6H,1-4H3

InChIKey

FPKOARNUITZHCF-UHFFFAOYSA-N

SMILES

N1C(N2C(C)=CC(C)=N2)=NN=C(N2C(C)=CC(C)=N2)N=1

3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine Usage And Synthesis

Uses

3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine is a reagent used to prepare 3-arylamino-6-benzylamino-1,2,4,5-tetrazines with antimalarial activities.

Synthesis

General procedure for the synthesis of 3,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2-dihydro-1,2,4,5-tetrazine from 3,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine: 26.2 g of sodium nitrite was dissolved in 588 mL of water, 60 mL of dichloromethane was added, and the mixed solution was cooled to 0 °C. Subsequently, 37 g (0.136 mol) of 3,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2-dihydro-1,2,4,5-tetrazine was added to the solution and 18.67 mL (0.326 mol) of acetic acid was added slowly and dropwise. After the gas escape ceased, extraction was carried out with dichloromethane and the organic phase was washed with potassium carbonate solution. After drying over magnesium sulfate, the organic solvent was removed by rotary evaporation and finally recrystallized with ether to afford the target product 3,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine (33.45 g, 91% yield).

References

[1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 8, p. 2049 - 2050
[2] Chemical Communications, 2013, vol. 49, # 87, p. 10275 - 10277
[3] Dalton Transactions, 2017, vol. 46, # 8, p. 2471 - 2478
[4] Journal of Chemical Crystallography, 2012, vol. 42, # 6, p. 600 - 605
[5] European Journal of Organic Chemistry, 2009, # 35, p. 6121 - 6128