5-Chloroindole-3-carboxylic acid Chemical Properties

Melting point:

234-235 °C

Boiling point:

449.7±25.0 °C(Predicted)

Density 

1.548±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.69±0.30(Predicted)

Appearance

Off-white to brown Solid

InChI

InChI=1S/C9H6ClNO2/c10-5-1-2-8-6(3-5)7(4-11-8)9(12)13/h1-4,11H,(H,12,13)

InChIKey

XUDITEOFEQOSAK-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(Cl)C=C2)C(C(O)=O)=C1

CAS DataBase Reference

10406-05-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933998090

5-Chloroindole-3-carboxylic acid Usage And Synthesis

Uses

5-Chloroindole-3-carboxylic acid is a pharmaceutical intermediate compound that can be used in the preparation of compounds and compositions for the treatment of disorders associated with sting activity.

Synthesis

5.0 g (33.0 mmol) of commercially available 5-chloro-1H-indole was dissolved in 50 mL of anhydrous N,N-dimethylformamide (DMF) and the reaction system was kept at 0°C. Slowly 7.35 g (35.0 mmol) of trifluoroacetic anhydride was added dropwise to the above solution. After the dropwise addition, the reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was slowly poured into 200 mL of ice water and the precipitate was collected by filtration. The resulting precipitate was suspended in 200 mL of 20% sodium hydroxide (NaOH) aqueous solution and heated at reflux overnight. After cooling, the aqueous phase was extracted twice with dichloromethane (100 mL each time). The organic phases were combined and the aqueous phase was acidified to pH 2-3 with concentrated hydrochloric acid to precipitate a solid. The crystalline product was collected by filtration and washed with a small amount of cold water. Finally, the product was dried in a vacuum drying oven to give 6.0 g of 5-chloroindole-3-carboxylic acid in 93% yield.

References

[1] Patent: US2004/9976, 2004, A1. Location in patent: Page/Page column 52
[2] Patent: EP1266897, 2002, A2. Location in patent: Page 74
[3] Patent: US6410562, 2002, B1

5-Chloroindole-3-carboxylic acid(10406-05-0)Related Product Information

• Indole-3-carboxylic acid
• Indole
• Indole-3-butyric acid
• 5-Chloroindole
• Folic acid
• Indometacin
• Indole-3-acetic acid
• 5-CHLOROINDOLE-2-CARBOXYLIC ACID METHYL ESTER
• 5-Nitropyridine-2-carboxylic acid
• 5-Hydroxyindole-2-carboxylic acid
• 5-CHLOROISOINDOLINE HYDROCHLORIDE
• Citric acid
• 5-CHLORO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER
• Ascoric Acid
• 5-Chloroindole-3-carboxaldehyde
• 5-CHLOROINDOLE-3-ACETIC ACID
• Methyl 2-(5-chloro-1H-indol-3-yl)acetate
• 5-CHLOROTRYPTOPHOL