1H-INDAZOL-4-AMINE Chemical Properties

Melting point:

148-150°C

Boiling point:

376.6±15.0 °C(Predicted)

Density 

1.367±0.06 g/cm3(Predicted)

storage temp. 

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

pka

15.61±0.40(Predicted)

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C7H7N3/c8-6-2-1-3-7-5(6)4-9-10-7/h1-4H,8H2,(H,9,10)

InChIKey

MDELYEBAXHZXLZ-UHFFFAOYSA-N

SMILES

N1C2=C(C(N)=CC=C2)C=N1

Safety Information

Hazard Codes 

Xn

Risk Statements 

34-22-36/37/38

Safety Statements 

26-36/37/39-22

RIDADR 

3259

HazardClass 

IRRITANT

HS Code 

29339900

1H-INDAZOL-4-AMINE Usage And Synthesis

Chemical Properties

Grey solid

Synthesis

The general procedure for the synthesis of 4-aminoindazole from 4-nitroindazole is as follows: 1. 2-Methyl-3-nitroaniline (2.27 g, 14.91 mmol) was dissolved in acetic acid (60 mL) and an aqueous solution of sodium nitrite (1.13 g, 1.1 eq.) was added (5 mL). After 2 hours of reaction, the dark red solution was poured into ice/water and the precipitate was collected by filtration to give 4-nitro-1H-indazole (1.98 g, 81% yield). 2. 4-Nitro-1H-indazole (760 mg, 4.68 mmol), charcoal-loaded palladium (10%, catalyst), and ethanol (30 mL) were stirred under a hydrogen balloon for 4 hours. Upon completion of the reaction, the solvent was removed in vacuum by filtration through diatomaceous earth to afford 1H-indazol-4-ylamine (631 mg, 100% yield). 3. A suspension of 1H-indazol-4-ylamine (63 mg, 4.74 mmol) in 6 M hydrochloric acid (7.2 mL) was added dropwise to an aqueous solution (2 mL) of sodium nitrite (337 mg, 4.89 mmol) at below 0 °C. After stirring for 30 min, sodium tetrafluoroborate (724 mg) was added. The reaction mixture formed a viscous solution, which was filtered and washed briefly with water to give 1H-indazole-4-diazotetrafluoroborate (218 mg, 20% yield) as a dark red solid. 4. Dry methanol (4 mL) was purged with argon for 5 min and 1H-indazole-4-diazotetrafluoroborate (218 mg, 0.94 mmol), bis(pinacolato)diboron (239 mg, 1.0 eq.), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride (20 mg) were added. The reaction mixture was stirred for 5 hours and then filtered through diatomaceous earth. The residue was purified by fast chromatography to afford the target product 4-aminoindazole (117 mg).

References

[1] Patent: WO2006/46031, 2006, A1. Location in patent: Page/Page column 31-33
[2] Patent: WO2007/42806, 2007, A1. Location in patent: Page/Page column 32-33
[3] Patent: US2008/76768, 2008, A1. Location in patent: Page/Page column 9
[4] Patent: US2008/76758, 2008, A1. Location in patent: Page/Page column 74
[5] Patent: WO2012/82997, 2012, A1. Location in patent: Page/Page column 78

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