Indole-3-acetone Chemical Properties

Melting point:

116°C

Boiling point:

303.86°C (rough estimate)

Density 

1.0898 (rough estimate)

refractive index 

1.4950 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

16.67±0.30(Predicted)

color 

tan

InChI

InChI=1S/C11H11NO/c1-8(13)6-9-7-12-11-5-3-2-4-10(9)11/h2-5,7,12H,6H2,1H3

InChIKey

LDVHYJKRIKBISQ-UHFFFAOYSA-N

SMILES

C(C1C2=C(NC=1)C=CC=C2)C(=O)C

CAS DataBase Reference

1201-26-9(CAS DataBase Reference)

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:Indole-3-acetone
• Language:English Provider:SigmaAldrich

Indole-3-acetone Usage And Synthesis

Chemical Properties

mp 115-117°C

Uses

3-Indolylacetone is an indole derivative that may act as a benzodiazepine receptor inhibitor.

Synthesis

a) Under argon protection, 2-(1H-indol-3-yl)-N-methoxy-N-methylacetamide (3.00 g, 13.75 mmol) was dissolved in anhydrous THF (60 mL) and the solution was cooled to 0 °C. A THF solution of methylmagnesium bromide (27.49 mL, 27.49 mmol) was added slowly and dropwise with continuous stirring. After 2 hours of reaction, the same amount of methylmagnesium bromide solution (27.49 mL, 27.49 mmol) was added again, and a third addition of methylmagnesium bromide solution (27.49 mL, 27.49 mmol) was made after 3 hours. Upon completion of the reaction, the reaction was quenched by the addition of saturated aqueous ammonium chloride solution, followed by the addition of ethyl acetate (EA) for extraction. The organic phase was separated, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (gradient elution) as eluent to afford the target product indole-3-acetone (2.35 g). The product was analyzed by LC/MS (method LC5): retention time (RT) = 1.56 min; mass-to-charge ratio (m/z) = 174.1 [M + H]+.

References

[1] Chemical Communications, 2018, vol. 54, # 16, p. 2048 - 2051
[2] Patent: EP3318563, 2018, A1. Location in patent: Paragraph 0155

Indole-3-acetone(1201-26-9)Related Product Information

• Indometacin
• 3-(3-Indolyl)-2-oxopropanoic acid
• Indole-3-butyric acid
• Diethyl (2-oxopropyl)phosphonate
• Indole
• Indole-3-acetic acid
• INDOLE-2,5-DICARBOXYLIC ACID 2-ETHYL ESTER 5-METHYL ESTER
• Indole-5-carboxylic acid
• Methyl indole-5-carboxylate
• Indole-4-carboxylic acid
• 3-Indolepropionic acid
• 3-Indoleacetonitrile
• Methyl 1H-indole-7-carboxylate
• Indole-6-boronic acid pinacol ester
• INDOLE-2-ACETIC ACID
• methyl indoline-5-carboxylate
• Piperonyl acetone
• Indole-6-carboxaldehyde