5-bromo-1H-indazole Chemical Properties

Melting point:

131-135 °C(lit.)

Boiling point:

333.8±15.0 °C(Predicted)

Density 

1.770±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

12.74±0.40(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C7H5BrN2/c8-6-1-2-7-5(3-6)4-9-10-7/h1-4H,(H,9,10)

InChIKey

STVHMYNPQCLUNJ-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(Br)C=C2)C=N1

CAS DataBase Reference

53857-57-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xn

Risk Statements 

25-36/37/38-22-41

Safety Statements 

26-36-36/37/39-22-39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

NI3517450

Hazard Note 

Harmful

HS Code 

29339900

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Dam. 1

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-bromo-1H-indazole Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

5-bromo-1H-indazole (5-BIA) is an indazole compound that can be used as a raw material in organic synthesis for the preparation of compounds such as 5-Iodo-1H-indazole and 3,5-Dibromo-1H-indazole. 5-BIA and its derivatives (7-BIA) can also be used as a highly effective corrosion inhibitor for copper and the protective ability of 5-BIA is more prominent than that of 7-BIA. 5-BIA and its derivatives (7-BIA) can also be used as highly efficient corrosion inhibitors for copper, and 5-BIA has a more prominent protective ability than 7-BIA. 1.5 mM 5-BIA and 1.5 mM 7-BIA have corrosion inhibition efficiencies (ηE) as high as 97.1 % and 94.0 %, respectively^[1].

Synthesis

In a dry 500 mL reaction flask, NaNO2 ( 3.89 g , 56.3 mmol) and water ( 10 m L ) were sequentially added to an acetic acid solution ( 300 mL ) of 4-bromo-o-toluidine ( 10.5 g , 56.3 mmol). The resulting reaction mixture was stirred at room temperature for 5 h. The progress of the reaction was monitored by TLC dot plate, and when the reaction was finished, the reaction mixture was concentrated directly under vacuum, and then the residue was diluted with ethyl acetate, and the ethyl acetate layer was washed sequentially with saturated aqueous NaHCO3 solution and brine. The organic layer was separated and dried over anhydrous Na2SO4, the desiccant was removed by filtration and the resulting filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography (0-50% ethyl acetate in n-hexane) to obtain 5-bromoindazole, note that if the product obtained by isolation is liquid, it can be solidified by adding n-hexane to it, shaking it and spinning it dry.

References

[1] JIE ZENG . Adsorption films based on indazole derivatives for application to protect Cu in sulfuric acid: Experimental and theoretical approaches[J]. Journal of the Taiwan Institute of Chemical Engineers, 2023. DOI:10.1016/j.jtice.2023.105134.

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