5-Fluoroindole-2-carboxylic acid Chemical Properties

Melting point:

259 °C (dec.)(lit.)

Boiling point:

422.2±25.0 °C(Predicted)

Density 

1.3231 (estimate)

storage temp. 

Inert atmosphere,2-8°C

form 

Crystalline Powder

pka

4.27±0.30(Predicted)

color 

Yellow-brown

Water Solubility 

Insoluble

BRN 

153217

InChI

InChI=1S/C9H6FNO2/c10-6-1-2-7-5(3-6)4-8(11-7)9(12)13/h1-4,11H,(H,12,13)

InChIKey

WTXBRZCVLDTWLP-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(F)C=C2)C=C1C(O)=O

CAS DataBase Reference

399-76-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

36/37/38-15-10

Safety Statements 

26-37/39-43-36-7/8

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:5-Fluoro-1H-indole-2-carboxylic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Fluoroindole-2-carboxylic acid Usage And Synthesis

Chemical Properties

yellow-brown crystalline powder

Uses

5-Fluoroindole-2-carboxylic acid,is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

Uses

Reactant for the synthesis of:

• Fungicidal agents
• Antitumor agents
• 2,3-dioxygenase (IDO) inhibitors
• Factor Xa inhibitors
• Enantioselective D3 receptor antagonists
• Ligands for hFPRL1 (or ALXR) receptor in inflammation
• Antibacterial agents
• Inhibitors of hepatitis C virus NS3·4A protease

Definition

ChEBI: 5-fluoro-1H-indole-2-carboxylic acid is an indolyl carboxylic acid.

General Description

5-Fluoroindole-2-carboxylic acid is an antagonist of the glycine site within the NMDA (N-methyl-D-aspartate) receptor complex.

Synthesis

General procedure for the synthesis of 5-fluoroindole-2-carboxylic acid from ethyl 5-fluoroindole-2-carboxylate: 103.6 g of ethyl 5-fluoroindole-2-carboxylate was dissolved in a mixed solution consisting of 31.25 g of 96% sodium hydroxide, 183 mL of methanol, and 183 mL of water, and heated at reflux for 1 hour. After the reaction was completed, the reaction solution was cooled to 50 °C, and the pH was adjusted to 3-4 by slowly adding 10% hydrochloric acid solution dropwise.After the reaction solution was completely cooled, the precipitate was collected by filtration to obtain 84.7 g of off-white 5-fluoroindole-2-carboxylic acid in 95% yield, which was shown to contain ≥96% by HPLC analysis.

References

[1] Patent: CN104402795, 2017, B. Location in patent: Paragraph 0040; 0043
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 3938 - 3942
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 3149 - 3157
[4] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1954, vol. 297, p. 229,233
[5] Journal of the Chemical Society, 1955, p. 1283,1284

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