1H-INDAZOLE-4-CARBOXYLIC ACID Chemical Properties

Melting point:

ca 280℃

Boiling point:

443.7±18.0 °C(Predicted)

Density 

1.506±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.35±0.30(Predicted)

form 

Crystalline Powder

color 

White to cream

InChI

InChI=1S/C8H6N2O2/c11-8(12)5-2-1-3-7-6(5)4-9-10-7/h1-4H,(H,9,10)(H,11,12)

InChIKey

KGKZHHIUOZGUNP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

677306-38-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-36-22

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

29339980

1H-INDAZOLE-4-CARBOXYLIC ACID Usage And Synthesis

Synthesis

The general procedure for the synthesis of indazole-4-carboxylic acid from 4-bromo-1H-indazole was as follows: sodium hydride (60% dispersed in mineral oil, 1.11 eq.) was added batchwise to an anhydrous tetrahydrofuran (7 L/mol) solution of 4-bromo-1H-indazole (1.00 eq.) at room temperature. The resulting solution was stirred at room temperature for 30 minutes and subsequently cooled to -60°C. A cyclohexane solution of 1.3 M sec-butyl lithium (2.1 eq.) was slowly added while keeping the internal temperature below -50 °C. Stirring of the reaction mixture was continued at -50 °C for 2 hours. Subsequently, a steady stream of anhydrous carbon dioxide gas was passed into the reaction mixture for 1 hour. While maintaining the carbon dioxide gas stream, the reaction mixture was allowed to gradually warm up to room temperature. Brine (6 L/mol) was added and the pH of the mixture was adjusted with concentrated hydrochloric acid to 5. The mixture was extracted with warm ethyl acetate (3 x 8 L/mol), the organic phases were combined, washed with a small amount of brine, dried over anhydrous sodium sulfate and concentrated. Finally, indazole-4-carboxylic acid was purified by silica gel column chromatography or crystallization.

References

[1] Patent: WO2004/29050, 2004, A1. Location in patent: Page 103;104

1H-INDAZOLE-4-CARBOXYLIC ACID(677306-38-6)Related Product Information

• 5-Carboxyindazole hydrochloride
• Indazole-3-carboxylic acid
• 1H-INDAZOLE-3-CARBOXYLIC ACID ETHYL ESTER
• INDAZOLE-5-CARBOXYLIC ACID METHYL ESTER
• Indazole
• Indazole-4-boronic acid, hydrochloride
• 1H-INDAZOLE-5-CARBALDEHYDE
• 1H-INDAZOLE-5-CARBONITRILE
• 7-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-1H-INDAZOLE
• 1H-INDAZOL-7-YL BORONIC ACID
• (1H-INDAZOL-3-YL)-ACETIC ACID
• 6-INDAZOLYBORONIC ACID
• Indole-4-carboxylic acid
• methyl indoline-5-carboxylate
• INDAZOLE-4-CARBOXYLIC ACID METHYL ESTER
• 5-Fluoro-3-indazolecarboxylic acid
• 5-Amino-1H-indazole-3-carboxylic acid methyl ester,1H-Indazole-3-carboxylic acid, 5-amino-, methyl ester
• 1-Methylindazole-3-carboxylic acid