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Indole-3-acetone

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Indole-3-acetone Basic information
Product Name:Indole-3-acetone
Synonyms:3-INDOLYLACETONE;2-Propanone, 1-(1H-indol-3-yl);3-(2-Oxopropyl)indole;3-Acetonylindole;Indol-3-yl-2-propanone;1-(1H-Indol-3-yl)-2-propanone;1-(1H-Indole-3-yl)acetone;3-(2-Oxopropyl)-1H-indole
CAS:1201-26-9
MF:C11H11NO
MW:173.21
EINECS:214-855-4
Product Categories:Indoles and derivatives;Aromatic Ketones (substituted);Indole;Indoles
Mol File:1201-26-9.mol
Indole-3-acetone Structure
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
pka16.67±0.30(Predicted)
color tan
InChIInChI=1S/C11H11NO/c1-8(13)6-9-7-12-11-5-3-2-4-10(9)11/h2-5,7,12H,6H2,1H3
InChIKeyLDVHYJKRIKBISQ-UHFFFAOYSA-N
SMILESC(C1C2=C(NC=1)C=CC=C2)C(=O)C
CAS DataBase Reference1201-26-9(CAS DataBase Reference)
Safety Information
WGK Germany 3
MSDS Information
ProviderLanguage
Indole-3-acetone English
SigmaAldrich English
Indole-3-acetone Usage And Synthesis
Chemical Propertiesmp 115-117°C
Uses3-Indolylacetone is an indole derivative that may act as a benzodiazepine receptor inhibitor.
Synthesis
Methylmagnesium Bromide

75-16-1

2-(1H-indol-3-yl)-N-Methoxy-N-MethylacetaMide

132922-37-3

Indole-3-acetone

1201-26-9

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 Preparation Products And Raw materials
Raw materialsMethylmagnesium Bromide-->2-(1H-indol-3-yl)-N-Methoxy-N-MethylacetaMide
Tag:Indole-3-acetone(1201-26-9) Related Product Information
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