4-AMINO-1,3,5-TRIMETHYLPYRAZOLE Chemical Properties

Melting point:

96 °C

Boiling point:

236℃

Density 

1.13

Flash point:

97℃

storage temp. 

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

form 

solid

pka

4.75±0.10(Predicted)

color 

Brown

BRN 

110739

InChI

InChI=1S/C6H11N3/c1-4-6(7)5(2)9(3)8-4/h7H2,1-3H3

InChIKey

SSDGMKHZMNTWLS-UHFFFAOYSA-N

SMILES

N1(C)C(C)=C(N)C(C)=N1

CAS DataBase Reference

28466-21-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

RTECS 

UQ6125100

HS Code 

2933199090

Toxicity

mouse,LD50,subcutaneous,> 500mg/kg (500mg/kg),Farmaco, Edizione Scientifica. Vol. 25, Pg. 592, 1970.

MSDS

• Language:English Provider:ALFA

4-AMINO-1,3,5-TRIMETHYLPYRAZOLE Usage And Synthesis

Definition

ChEBI: 1,3,5-Trimethyl-1H-pyrazol-4-amine is a member of pyrazoles.

Synthesis

General procedure for the synthesis of 4-amino-1,3,5-trimethylpyrazole from 4-nitro-1,3,5-trimethylpyrazole: To a solution of 1,3,5-trimethyl-4-nitro-1H-pyrazole (2.1 g, 1.35 mmol) in ethanol (30 mL) was added powdered iron (14.85 g, 27 mmol) and 6N aqueous hydrochloric acid solution (0.23 mL. 0.67 mmol) and the mixture was refluxed for 16 hours. After completion of the reaction (monitored by TLC), the solvent was removed by evaporation under reduced pressure. The crude product was alkalized with 0.5 N aqueous sodium hydroxide and extracted with 10% methanol-dichloromethane (10%, 50 mL) solution. The organic layer was dried with anhydrous sodium sulfate, filtered and the solvent evaporated to afford 4-amino-1,3,5-trimethylpyrazole as a beige solid (1.68 g, 99% yield).' HNMR (400 MHz, DMSO-d6): δ 3.50 (s, 3H), 3.27 (bs, 2H), 2.03 (s, 3H), 1.94 (s, 3H).

References

[1] Patent: WO2015/25197, 2015, A1. Location in patent: Paragraph 00095
[2] Patent: WO2015/113452, 2015, A1. Location in patent: Page/Page column 55
[3] Patent: EP1203767, 2002, A1. Location in patent: Example 39
[4] Chemische Berichte, 1895, vol. 28, p. 688
[5] Journal fuer Praktische Chemie (Leipzig), 1896, vol. <2> 53, p. 127

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