Ethyl 5-chloro-2-indolecarboxylate Chemical Properties

Melting point:

166-168 °C (lit.)

Boiling point:

375.0±22.0 °C(Predicted)

Density 

1.2405 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Powder or Crystals

pka

14.10±0.30(Predicted)

color 

Yellow to orange to tan or light brown

BRN 

170255

InChI

InChI=1S/C11H10ClNO2/c1-2-15-11(14)10-6-7-5-8(12)3-4-9(7)13-10/h3-6,13H,2H2,1H3

InChIKey

LWKIFKYHCJAIAB-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

4792-67-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-37-26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:2-(Ethoxycarbonyl)-5-chloro-indole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl 5-chloro-2-indolecarboxylate Usage And Synthesis

Chemical Properties

yellowish to light brown crystalline powder

Uses

Ethyl 5-chloro-2-indolecarboxylate was used in the synthesis of anti-allergic agents.

Uses

5-Chloroindole-2-carboxylic acid ethyl ester is a used in the synthetic preparation of a potent anticonvulsant Ethyl 4-methylamino-5,7-dichloro-2-quinolinecarboxylate.

Synthesis

General procedure for the synthesis of ethyl 5-chloroindole-2-carboxylate from ethyl 2-[(4-chlorophenyl)hydrazinylidene]propionate: 500 g of polyphosphoric acid was mixed with 250 g of phosphoric acid and heated to 70 °C under stirring. 70 g of raw material 4-chlorophenylhydrazine pyruvic acid phenylhydrazone was added in batches, and the reaction temperature was controlled in the range of 70-90 °C. After 1 hour of reaction, it was confirmed that the feedstock was completely consumed. The reaction temperature was continued to be maintained for 40 minutes to ensure complete reaction. After completion of the reaction, the reaction mixture was poured into 1500 g of ice-water mixture and cooled to room temperature. The precipitate was collected by filtration and dried to give a light yellow solid product. Upon further drying, 58 g of ethyl 5-chloroindole-2-carboxylate was obtained in 90% yield.

References

[1] Patent: CN104402795, 2017, B. Location in patent: Paragraph 0045; 0047
[2] Journal of the Chemical Society, 1955, p. 3499,3502
[3] Journal of Medicinal Chemistry, 1988, vol. 31, # 5, p. 944 - 948
[4] Archiv der Pharmazie, 2008, vol. 341, # 5, p. 294 - 300
[5] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021

Ethyl 5-chloro-2-indolecarboxylate(4792-67-0)Related Product Information

• Indole-2-carboxylic acid
• 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester
• Ethyl cyanoacetate
• Ethyl chloroacetate
• Indole
• Ethyl acetate
• Indometacin
• Ethyl formate
• Ethyl 2-chloroacetoacetate
• Ethyl acrylate
• Ethylparaben
• ISOXADIFEN-ETHYL
• Methyl acrylate
• Ethyl pyruvate
• Ethanol
• 5-Chloroindole
• Tris(trimethylsilyl)phosphate
• 5-Chloroindole-2-carboxylic acid