| Identification | Back Directory | [Name]
4-Iodo-1H-indazol-3-ylamine | [CAS]
599191-73-8 | [Synonyms]
3-Amino-4-iodoindazole
4-iodo-1H-indazol-3-amine
3-Amino-4-iodo-1H-indazole
4-Iodo-1H-indazol-3-ylamine
1H-Indazol-3-aMine, 4-iodo-
3-Amino-4-iodo-1H-indazol... | [Molecular Formula]
C7H6IN3 | [MDL Number]
MFCD03426697 | [MOL File]
599191-73-8.mol | [Molecular Weight]
259.05 |
| Chemical Properties | Back Directory | [Melting point ]
154-155° | [Boiling point ]
452.2±25.0 °C(Predicted) | [density ]
2.168±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Crystalline Solid | [pka]
13.85±0.40(Predicted) | [color ]
Off-white to brown |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 3-amino-4-iodoindazole from 2-fluoro-6-iodobenzonitrile: 500 mg of 2-fluoro-6-iodobenzonitrile and 1.3 ml of 85% hydrazine hydrate were dissolved in 10 ml of n-butanol and heated to 110 °C. The reaction mixture was stirred for 6 hours and then cooled to room temperature. Liquid-liquid separation was carried out by adding water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated to give 502 mg of 4-iodo-1H-indazol-3-amine as a brown solid in 96% yield.1H NMR (300 MHz, DMSO-d6) δ (ppm): 5.05 (s, 2H), 6.90-6.96 (m, 1H), 7.29 (d, J = 8.1 Hz, 1H), 7.34 (d, J = 7.5 Hz, 1H), 11.80 (s, 1H). | [References]
[1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597
[2] Patent: EP3112351, 2017, A1. Location in patent: Paragraph 0029
[3] Organic Process Research and Development, 2009, vol. 13, # 6, p. 1419 - 1425
[4] European Journal of Medicinal Chemistry, 2015, vol. 104, p. 139 - 147
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1584 - 1597 |
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