Ethyl 3-indoleacetate Chemical Properties

Melting point:

44-45 °C(lit.)

Boiling point:

164-166 °C1 mm Hg(lit.)

Density 

1.1255 (rough estimate)

refractive index 

1.5260 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

16.70±0.30(Predicted)

form 

Crystalline Powder

color 

White

Water Solubility 

insoluble

BRN 

171682

CAS DataBase Reference

778-82-5(CAS DataBase Reference)

NIST Chemistry Reference

1H-Indole-3-acetic acid, ethyl ester(778-82-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-21/22

Safety Statements 

36/37/39-26-24/25

WGK Germany 

3

RTECS 

NL3528000

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Ethyl 3-indoleacetate Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

Reactant for preparation of:• ;Pesticides1• ;Anti-inflammatory agents2• ;Antibacterial and antifungal agents• ;Anticonvulsant agents • ;Hypotensive agents3• ;Analgesic agents4

Uses

Ethyl Indole-3-acetate is a compound used in the synthesis of 9H-Pyrrolo[1,2-α]Indoles via Michael Addition-Condensation with α,β-Unsaturated Ketimines.

Uses

Reactant for preparation of:

• Pesticides
• Anti-inflammatory agents
• Antibacterial and antifungal agents
• Anticonvulsant agents
• Hypotensive agents
• Analgesic agents

Definition

ChEBI: Ethyl 3-indoleacetate is a member of indole-3-acetic acids.

Synthesis

Indol-3-ylacetic acid (1.00 g, 5.71 mmol) was dissolved in 25 mL of ethanol and concentrated sulfuric acid (1.0 mL, 18.4 mmol) was added. The reaction mixture was stirred under reflux conditions for 2 hours. Upon completion of the reaction, the mixture was cooled to 0 °C in an ice bath and subsequently neutralized with 2 N sodium hydroxide solution. The organic solvent was removed by evaporation under reduced pressure and the residue was partitioned between dichloromethane and water. The aqueous phase was extracted twice with dichloromethane, and the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 1.02 g (5.02 mmol, 88% yield) of ethyl indole-3-acetate as a brown oil. The product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 300 MHz, CDCl3): δ 8.09 (br.s, 1H), 7.63 (d, J = 7.69 Hz, 1H), 7.35 (d, J = 7.69 Hz, 1H), 7.04-7.25 (m, 3H), 4.17 (q, J = 7.14 Hz, 2H), 3.77 (s, 2H), 1.26 (t, J = 7.14 Hz, 3H). Ultra performance liquid chromatography-mass spectrometry (UPLC/MS) analysis showed a retention time of 1.58 min, and low resolution mass spectrometry (LRMS) measured m/z 204 ([M+1]+).

References

[1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1777 - 1779
[2] Arzneimittel-Forschung/Drug Research, 2001, vol. 51, # 10, p. 814 - 824
[3] Patent: EP2548863, 2013, A1. Location in patent: Paragraph 0247
[4] Patent: WO2013/10881, 2013, A1. Location in patent: Page/Page column 95-96
[5] Chinese Chemical Letters, 2013, vol. 24, # 2, p. 127 - 130

Ethyl 3-indoleacetate(778-82-5)Related Product Information

• Ethanol
• Indole
• Ethyl acrylate
• Ethyl cellulose
• CHLOROETHANE
• Ethylparaben
• Ethylbenzene
• Ethyl 2-(Chlorosulfonyl)acetate
• Ethyl formate
• Ethyl acetate
• Indole-3-acetic acid
• METHYL 3-INDOLYLACETATE
• PINACOL ESTER INDOLE-5-BORONIC ACID
• ETHYL INDOLE-2-ACETATE
• 3-Indolepropionic acid
• 1H-INDAZOLE-5-CARBALDEHYDE
• 3-(3-Indolyl)-2-oxopropanoic acid
• INDOLE-3-ACETIC ACID