3-Acetylindole

Base Information

• Chemical Name: 3-Acetylindole
• CAS No.: 703-80-0
• Molecular Formula: C10H9NO
• Molecular Weight: 159.188
• Hs Code.: 29339990
• European Community (EC) Number: 211-875-5
• NSC Number: 58084,47180
• UNII: 0HAT270V6U
• DSSTox Substance ID: DTXSID10220570
• Nikkaji Number: J41.561H
• Wikidata: Q27236784
• ChEMBL ID: CHEMBL553944
• Mol file: 703-80-0.mol

Synonyms:3-acetylindole

Chemical Property of 3-Acetylindole

Chemical Property:

• Appearance/Colour: yellow to light brown powder
• Vapor Pressure: 0.000132mmHg at 25°C
• Melting Point: 188-192 °C(lit.)
• Refractive Index: 1.648
• Boiling Point: 333.9 °C at 760 mmHg
• PKA: 15.38±0.30(Predicted)
• Flash Point: 163.7 °C
• PSA: 32.86000
• Density: 1.193 g/cm³
• LogP: 2.37050
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO; Dichloromethane; Methanol
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 159.068413911
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

3-Acetylindole ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CNC2=CC=CC=C21
• General Description: 3-Acetylindole, also known as 1-(1H-Indol-3-yl)ethanone or 3-Indolyl methyl ketone, is a 3-substituted indole derivative with an electron-withdrawing acetyl group. It reacts efficiently with sodium naphthalenide, a single electron transfer (SET) reagent, to yield a single product, demonstrating high selectivity and reactivity due to the acetyl group's ability to lower the LUMO energy of the indole ring. This makes 3-acetylindole a suitable substrate for SET-mediated synthetic transformations in the construction of indole derivatives.

Technology Process of 3-Acetylindole

There total 89 articles about 3-Acetylindole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(3-(1-tert-butoxycarbonyl)indolyl)-1-ethanone (124688-00-2) → 3-acetylindole (703-80-0)

Guidance literature:

With 2,3-dimethyl-buta-1,3-diene; In toluene; at 250 ℃; for 22h; Inert atmosphere;

DOI:10.1016/j.tet.2011.04.030

Reference yield: 100.0%

C16H12N2O5S (1312675-88-9) → 3-acetylindole (703-80-0)

Guidance literature:

With diethylaluminium chloride; 2,3-dimethyl-buta-1,3-diene; In hexane; dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.tet.2011.04.030

Reference yield: 96.0%

3-acetyl-N-(p-toluenesulfonyl)indole (104142-24-7) → 3-acetylindole (703-80-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl acetamide; at 60 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.152442

upstream raw materials:

quinoline

1-indol-3-yl-ethanone-hydrazone

N-methyl-acetamide

indole

Downstream raw materials:

1H-indole-3-carboxylic acid

2-iodo-1-(1H-indol-3-yl)ethanone

3-(4-hydroxy-phenyl)-1-(1H-indol-3-yl)-propenone

(2E)-1-(1H-indol-3-yl)-3-phenylprop-2-en-1-one

Refernces

Effect of sodium naphthalenide, a key set reagent, on 3-substituted indoles

10.3987/COM-04-10142

The research investigates the effects of sodium naphthalenide, a single electron transfer (SET) reagent, on 3-substituted indoles to explore the synthesis of indole derivatives through SET reactions. The study found that indoles with electron-donating substituents do not react with sodium naphthalenide, while those with electron-withdrawing substituents readily undergo reactions, yielding various products depending on the specific substituent. For instance, 3-trifluoroacetylindole, 3-acetylindole, and 3-benzoylindole each produced a single product, whereas 3-formylindole generated four products. The reactions involving electron-withdrawing groups were highly selective and efficient, with high yields of the desired products. The study concludes that SET reactions with sodium naphthalenide are an effective method for constructing indole derivatives when electron-withdrawing substituents are present on the indole ring, as these groups lower the LUMO energy of the indole ring, facilitating electron transfer from the reagent to the substrate.