7-chloro-1H-indole-2-carboxylic acid Chemical Properties

Boiling point:

449.7±25.0 °C(Predicted)

Density 

1.548±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

4.23±0.30(Predicted)

form 

solid

Appearance

White to off-white Solid

InChI

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

InChIKey

NVKAHBFPKVINGE-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2Cl)C=C1C(O)=O

Safety Information

HazardClass 

IRRITANT

HS Code 

2933998090

7-chloro-1H-indole-2-carboxylic acid Usage And Synthesis

Uses

7-chloro-1H-indole-2-carboxylic acid is an important pharmaceutical intermediate compound used in the preparation of protease inhibitors.

Synthesis

A mixture of 111.5 g of 7-chloroindole-2-carboxylate in 31.25 g of 96percent sodium hydroxide in 183 ml of methanol and 183 ml of water were heated under reflux for 1 hour, cooled to 45 ° C, and 10 percent hydrochloric acid was added dropwise to a pH of 3 to 4. The mixture was sufficiently cooled to obtain 89.7 g of product as an off-white 7-chloro-1H-indole-2-carboxylic acid.

References

[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 19, p. 3957 - 3960
[2] Patent: CN104402795, 2017, B. Location in patent: Paragraph 0060; 0063
[3] Journal of the Chemical Society, 1955, p. 3499,3502
[4] Patent: US2003/207893, 2003, A1
[5] Patent: WO2004/22061, 2004, A1. Location in patent: Page/Page column 56-57

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