| Identification | More | [Name]
6-Aminoindazole | [CAS]
6967-12-0 | [Synonyms]
6-AMINO-1H-INDAZOLE
6-AMINOBENZOPYRAZOLE
6-AMINOINDAZOLE
AKOS BBS-00003578
LABOTEST-BB LT00114795
1h-indazol-6-amine
6-Aminoidazole
Aminoidazole
indazol-6-ylamine
Aminoindazole
6-AMINO-1H-INDAZOLE 98%
6-Indazolamine
6-Amino-1,2-diaza-1H-indene | [EINECS(EC#)]
230-177-1 | [Molecular Formula]
C7H7N3 | [MDL Number]
MFCD00005696 | [Molecular Weight]
133.15 | [MOL File]
6967-12-0.mol |
| Chemical Properties | Back Directory | [Appearance]
light brown powder | [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 | [form ]
Powder | [pka]
15.61±0.40(Predicted) | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H315-H319-H335 | [Precautionary statements ]
P261-P264-P270-P301+P312-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
NK7712000
| [HS Code ]
29339980 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 |
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