6-Chloro-1H-indazole Chemical Properties

Melting point:

174-177℃

Boiling point:

309.5±15.0 °C(Predicted)

Density 

1.425±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

12.82±0.40(Predicted)

form 

solid

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C7H5ClN2/c8-6-2-1-5-4-9-10-7(5)3-6/h1-4H,(H,9,10)

InChIKey

VUZQHUVRBPILAX-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

6-Chloro-1H-indazole Usage And Synthesis

Application

6-Chloro-1H-indazole is a useful research chemical.

Synthesis

The general procedure for the synthesis of 6-chloro-1H-indazole from 5-chloro-o-toluidine was as follows: aqueous NaNO2 (13.80 g, 0.2 mol, 32.20 mL) was added slowly and dropwise at 0 °C into a reaction system containing 5-chloro-o-toluidine (21.40 g, 0.2 mol), H2O (190 mL), and an aqueous 12N HCl solution (50 mL, 0.6 mol) in a mixed reaction system. The reaction temperature was maintained at 0 °C and filtration was performed after continued stirring for 30 min. To the filtrate, pre-cooled aqueous NaBF4 solution (24.20 g, 0.22 mol dissolved in 90 mL of H2O) was added and stirred at 0 °C for 40 min. The resulting precipitate was collected by filtration, washed sequentially with cold ethanol (50 mL x 3) and cold ether (50 mL x 3), and subsequently concentrated under vacuum to give the diazonium salt (19.19 g) as a yellow solid. The diazonium salt (19.19 g, 0.093 mol) was dissolved in CHCl3 (231 mL) and KOAc (15.15 g, 0.155 mol) was added. The reaction mixture was stirred at room temperature for 4 h, after which the reaction was quenched with water (200 mL) and extracted with CH2Cl2 (70 mL x 3). The organic phases were combined, washed with brine (50 mL × 3), dried over anhydrous Na2SO4 and concentrated under reduced pressure. Finally, the crude product was purified by recrystallization to give 7.51 g of 6-chloro-1H-indazole.

Research

Indazoles are an essential class of heterocyclic compounds with many applications as biological and pharmaceutic agents. They have been extensively studied due to their interesting chemical and biological characteristics. Indazole belongs to the azoles family, which includes carbon, hydrogen and a nitrogen atom. Indazole has a heterocyclic structure made up of benzene and pyrazole rings. Indazole derivatives have a wide range of biological activities. For instance, indazole derivatives show vasorelaxant and anti-aggregator activities by stimulating NO release and increasing cGMP levels. K?ksal et al. investigated the in vitro inhibitory effects of some indazole derivatives. The inhibitory effects of molecules on enzyme activity were tested in vitro; Ki values were calculated using Lineweaver-Burk diagrams. Ki values were found as 252.78 ± 27.85 mM for 6-Chloro-1H-indazole. The results indicated that the indazole molecules had effective LPO inhibition. According to the results, the 6-Bromo-1H-indazole molecule had the strongest inhibitory effect, whereas the 6-Chloro-1H-indazole had the weakest inhibitory effect[1].

References

[1] Zeynep K?ksal, Zuhal Alim. “Lactoperoxidase, an antimicrobial enzyme, is inhibited by some indazoles.” Drug and Chemical Toxicology 43 1 (2020): 22–26.

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