3-Iodo-1H-indazole Chemical Properties

Melting point:

142 °C(Solv: water (7732-18-5))

Boiling point:

358.2±15.0 °C(Predicted)

Density 

2.082±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

12.04±0.40(Predicted)

form 

solid

color 

White

InChI

InChI=1S/C7H5IN2/c8-7-5-3-1-2-4-6(5)9-10-7/h1-4H,(H,9,10)

InChIKey

UDKYMMQGPNFWDA-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

29339900

3-Iodo-1H-indazole Usage And Synthesis

Chemical Properties

White solid

Uses

3-Iodo-1H-indazole is a halogenated indazole compound containing an iodine atom substituent at the 3-position. Due to its highly reactive structure, it can be used in arylation or halogenation reactions. It can also be used in the preparation of fluorinated pyrazoles and indazoles. It can be used in the pharmaceutical field as a raw material or intermediate component in the synthesis of biologically active drugs.

Synthesis

The synthesis of 3-iodoindazole was carried out according to the method previously reported by Bocchi [28] with slight modifications. The procedure was as follows: 1H-indazole (3 g, 25.4 mmol), iodine (12.7 g, 50.03 mmol) and potassium hydroxide (5.34 g, 95.25 mmol) were dissolved in DMF (7 mL) and the reaction was stirred for 3 h at room temperature. Upon completion of the reaction, saturated sodium bisulfite solution (150 mL) was added to quench the reaction, at which time a precipitate was generated. The precipitate was collected by vacuum filtration and washed with distilled water (3 x 30 mL). The resulting solid was dried overnight in a vacuum oven at 30 °C to give 6.17 g of light yellow solid product in 100% yield. The product was characterized as follows: melting point 136-138 °C (literature value [36]: 134-136 °C); IR (KBr) ν (cm-1): 3086 (NH), 424 (C-I); 1H-NMR δ (ppm): 13.50 (1H, s, H-1), 7.55 (1H, d, J=8.6 Hz, H-7), 7.45- 7.40 (2H, m, H-6 and H-4), 7.19 (1H, dd, J=7.5 Hz, H-5); 13C-NMR δ (ppm): 140.41, 127.22, 126.79, 121.23, 120.39, 110.51, 93.49; HRMS (calculated value C7H5IN2: 243.9497. measured value: 243.9499).

References

[1] Patent: WO2007/65010, 2007, A2. Location in patent: Page/Page column 84
[2] Molecules, 2018, vol. 23, # 8,
[3] Organic and Biomolecular Chemistry, 2015, vol. 13, # 26, p. 7257 - 7264
[4] Synlett, 2010, # 2, p. 219 - 222
[5] Patent: WO2015/25025, 2015, A1. Location in patent: Page/Page column 355

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