5-Chloroindole-2-carboxylic acid Chemical Properties

Melting point:

287 °C (dec.) (lit.)

Boiling point:

449.7±25.0 °C(Predicted)

Density 

1.3228 (rough estimate)

refractive index 

1.5790 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.26±0.30(Predicted)

color 

Beige

BRN 

153229

InChI

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

InChIKey

FUQOTYRCMBZFOL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

10517-21-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

NL5998400

HazardClass 

IRRITANT

HS Code 

29339990

MSDS

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

5-Chloroindole-2-carboxylic acid Usage And Synthesis

Chemical Properties

light pink to beige or light brown fine

Uses

NMDA receptor antagonist (gly)

Uses

5-Chloroindole-2-carboxylic Acid is used in the synthesis of 4-(3-aminomethylphenyl)piperidine-1-carboxamides as potent, selective, and orally bioavailable inhibitors of βII tryptase. It is also a reagent used to prepare indole amides with possible antihistaminic activities.

Definition

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

Synthesis

The general procedure for the synthesis of 5-chloroindole-2-carboxylic acid from ethyl 5-chloroindole-2-carboxylate was as follows: 111.5 g of ethyl 5-chloroindole-2-carboxylate was dissolved in a mixture of 31.25 g of 96% sodium hydroxide, 183 ml of methanol, and 183 ml of water, and was heated and refluxed for 1 hour. After the reaction was completed, the reaction solution was cooled to 40 °C, and 10% hydrochloric acid was slowly added dropwise to adjust the pH to 3-4. After the reaction solution was completely cooled, the precipitate was collected by filtration to obtain 90.1 g of off-white 5-chloroindole-2-carboxylic acid in 92.5% yield, and the purity of the product was ≥96% by high performance liquid chromatography (HPLC).

References

[1] Chemical Biology and Drug Design, 2017, vol. 90, # 1, p. 64 - 82
[2] Patent: CN104402795, 2017, B. Location in patent: Paragraph 0045; 0048
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 3149 - 3157
[4] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 3938 - 3942
[5] Journal of the Chemical Society, 1955, p. 3499,3502

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