Ethyl 5-hydroxyindole-2-carboxylate Chemical Properties

Melting point:

150-151°C

Boiling point:

410.4±25.0 °C(Predicted)

Density 

1.326±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

9.59±0.40(Predicted)

Appearance

Off-white to yellow Solid

Water Solubility 

Insoluble in water.

BRN 

476925

CAS DataBase Reference

24985-85-1(CAS DataBase Reference)

NIST Chemistry Reference

Ethyl 5-hydroxyindole-2-carboxylate(24985-85-1)

Safety Information

Safety Statements 

22-24/25

MSDS

• Language:English Provider:ALFA

Ethyl 5-hydroxyindole-2-carboxylate Usage And Synthesis

Uses

Ethyl 5-hydroxyindole-2-carboxylate is used as an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuffs.

Synthesis

General procedure for the synthesis of ethyl 5-hydroxyindole-2-carboxylate from ethyl 5-benzyloxyindole-2-carboxylate: ethyl 5-benzyloxyindole-2-carboxylate (10 g, 34 mmol) was dissolved in ethanol (250 mL), 10% Pd/C catalyst was added, and the hydrogenation reaction was carried out for 20 h at atmospheric pressure (using a double-walled balloon). Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate and filtered through diatomaceous earth to remove the catalyst. The filtrate was concentrated in vacuum to give ethyl 5-hydroxyindole-2-carboxylate (7 g, 99% yield) in brown solid form. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.86 (broad peak, 1H), 7.29 (d, J = 8.80 Hz, 1H), 7.11 (s, 1H), 7.06 (s, 1H), 6.94 (d, J = 8.70 Hz, 1H), 4.83 (broad peak, 1H), 4.42 (q, J = 7.09 Hz, 2H ), 1.41 (t, J = 7.08Hz, 3H).

References

[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 1, p. 5 - 8
[2] Patent: US6670388, 2003, B1. Location in patent: Page column 6
[3] Patent: US6469046, 2002, B1
[4] Patent: US6608059, 2003, B1
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 24, p. 10455 - 10463

Ethyl 5-hydroxyindole-2-carboxylate(24985-85-1)Related Product Information

• Ethylbenzene
• Ethyl cellulose
• Benzocaine
• CHLOROPHOSPHONAZO III
• Indole-2-carboxylic acid
• Ethyl acetate
• Ethyl formate
• Ethyl acrylate
• Ethanol
• Indole
• 5-Hydroxyindole
• Ethylparaben
• Tris(trimethylsilyl)phosphate
• Urethane
• 1H-INDOL-3-OL
• RESMETHRIN
• Ethyl chloroformate
• Diethyl ether