5-BROMO-1H-INDAZOLE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

289-292°C

Boiling point:

493.4±25.0 °C(Predicted)

Density 

1.946±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

2.81±0.30(Predicted)

form 

solid

color 

Off-white

InChI

InChI=1S/C8H5BrN2O2/c9-4-1-2-6-5(3-4)7(8(12)13)11-10-6/h1-3H,(H,10,11)(H,12,13)

InChIKey

AMJVXOOGGBPVCZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

1077-94-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Safety Statements 

22-26-36/37/39

Hazard Note 

Irritant

HS Code 

2933998090

5-BROMO-1H-INDAZOLE-3-CARBOXYLIC ACID Usage And Synthesis

Uses

5-Bromo-1H-indazole-3-carboxylic acid an important chemical product. It is mainly used as a raw material in chemical synthesis for the preparation of other compounds. Its derivative 5-Bromo-1H-indazole-3-carboxylic acid ethyl ester can be used as a protein kinase inhibitor, which can be used for the treatment and prevention of diseases.

Synthesis

Step 1: Indazole-3-carboxylic acid (CXXXI) (1.0 g, 6.16 mmol) was suspended in glacial acetic acid (60 mL) and heated to 120 °C until a clear solution was formed. The solution was then cooled to 90 °C. A solution of bromine (0.633 mL, 12.33 mmol) in glacial acetic acid (2 mL) was slowly added dropwise to the solution at 90 °C. After addition, the reaction continued to be heated at 90 °C for 16 hours. After completion of the reaction, the solution was cooled to room temperature and poured into ice water and stirred at room temperature for 15 minutes. The precipitated solid was filtered, washed with cold water and dried under vacuum at room temperature to afford 5-bromo-1H-indazole-3-carboxylic acid (CXXXII) as a white solid (1.30 g, 5.39 mmol, 87.5% yield). The product was characterized by 1H NMR (DMSO-d6): δ 13.95 (s, 1H), 13.18 (br s, 1H), 8.21 (d, J = 1.2 Hz, 1H), 7.65 (d, J = 7.0 Hz, 1H), 7.56 (dd, J = 7.0, 1.2 Hz, 1H); ESIMS m/z 242.0 ([M + H]+. (calculated value C8H4BrN2O2).

References

[1] Patent: US2015/266825, 2015, A1. Location in patent: Paragraph 1359; 1360
[2] Patent: WO2018/75858, 2018, A1. Location in patent: Paragraph 0371; 0372
[3] Patent: CN107573327, 2018, A. Location in patent: Paragraph 0067; 0068; 0069; 0070
[4] Patent: US2005/90529, 2005, A1. Location in patent: Page/Page column 84-85
[5] Chemische Berichte, 1922, vol. 55, p. 1141,1157

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