6-Aminoindazole Chemical Properties

Melting point:

204-206 °C (dec.) (lit.)

Boiling point:

376.6±15.0 °C(Predicted)

Density 

1.367±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

15.61±0.40(Predicted)

form 

Powder

color 

Tan

InChI

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

InChIKey

KEJFADGISRFLFO-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

6967-12-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

RTECS 

NK7712000

HS Code 

29339980

MSDS

• Language:English Provider:6-Aminoindazole
• Language:English Provider:SigmaAldrich

6-Aminoindazole Usage And Synthesis

Description

6-Aminoindazole is a tetronic acid derivative that has been shown to have an inhibitory effect on the activity of cyclopentyl and ethylene diamine. This drug also increases blood pressure in animals, and is found to be a potent inhibitor of thrombin receptor.

Chemical Properties

light brown powder

Application

6-Aminoindazole is structurally similar to quinoline derivatives and has been shown to have anticancer activity in human ovarian carcinoma cells. The affinity constants for this compound are higher than those for most other compounds with anti-cancer effects, which may be due to the presence of hydrogen bonds between the nitrogen atoms and the carbonyl group.

Definition

ChEBI: 1H-indazol-6-amine is a member of indazoles.

Synthesis

General procedure for the synthesis of 6-aminoindazole from 6-nitro-1H-indazole: 6-nitro-1H-indazole (25 g, 0.153 mol, commercially available) was mixed with 10% Pd/C catalyst (2.0 g) in methanol, and the reaction was stirred overnight under hydrogen atmosphere (1 atm). After completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford 6-amino-1H-indazole (18.5 g, 94% yield) as a yellow solid.

Purification Methods

It is recrystallised from H2O or EtOH and sublimes in a vacuum. [Beilstein 25 H 317.]

References

[1] Tetrahedron Letters, 2010, vol. 51, # 5, p. 786 - 789
[2] ChemCatChem, 2014, vol. 6, # 11, p. 3153 - 3159
[3] Tetrahedron, 2008, vol. 64, # 28, p. 6711 - 6723
[4] Patent: WO2006/71940, 2006, A2. Location in patent: Page/Page column 407
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3177 - 3180

6-Aminoindazole(6967-12-0)Related Product Information

• 5-23-06-00185 (Beilstein Handbook Reference)
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