23543-66-0

Basic information

• Product Name: 3-Methyl-1-acetyl-1H-indole
• Synonyms: 1-Acetyl-3-methyl-1H-indole;3-Methyl-1-acetyl-1H-indole;1-(3-methyl-1H-indol-1-yl)ethanone;1-(3-methylindol-1-yl)ethanone
• CAS NO: 23543-66-0
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.21
• Mol File: 23543-66-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 64-65℃
• Boiling Point: 282.6°C at 760 mmHg
• Flash Point: 124.7°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 0.00332mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: 3-Methyl-1-acetyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-1-acetyl-1H-indole(23543-66-0)
• EPA Substance Registry System: 3-Methyl-1-acetyl-1H-indole(23543-66-0)

Safety Data

• Hazardous Substances Data: 23543-66-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 63, p. 7652, 1998 DOI: 10.1021/jo9803277Tetrahedron Letters, 28, p. 5291, 1987 DOI: 10.1016/S0040-4039(00)96710-8

InChI:InChI=1/C11H11NO/c1-8-7-12(9(2)13)11-6-4-3-5-10(8)11/h3-7H,1-2H3

Upstream product

• 201230-82-2 carbon monoxide 
• 29124-68-3 N-(2-vinylphenyl)acetamide 
• 83-34-1 3-Methylindole 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 

Downstream Products

• 78388-92-8 1-(3-methyl-2-phenyl-1H-indol-1-yl)ethan-1-one 
• 83-34-1 3-Methylindole 
• 1441174-23-7 N-acetyl-3-(2-hydroxy-5-methylphenyl)-3-methylindoline 

Relevant articles and documents

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Interrupted Intramolecular Hydroaminomethylation of N-Protected-2-vinyl Anilines: Novel Access to 3-Substitued Indoles or Indoline-2-ols

A new synthetic alternative to the synthesis of 3-methyl indoles and 3-methyl indoline-2-ols with an excellent atomic economy is presented in this study. It is demonstrated that the intramolecular interrupted hydroaminomethylation (HAM) reaction is a powerful tool for the formation of these compounds, which exhibit wide-ranging biological activity. Several N-Protected-2-vinyl anilines were synthesized and involved in the reaction producing the corresponding 3-methylindole or 3-methyl indoline-2-ol depending on the nature of the N-protecting groups.

Sulfated Zirconia: An Efficient and Reusable Heterogeneous Catalyst in the Friedel–Crafts Acylation Reaction of 3-Methylindole

Abstract: An efficient process for the Friedel–Crafts acylation of 3-methylindole with acid anhydrides in the presence of sulfated zirconia was developed. This catalyst shows excellent catalytic activity with good conversion and selectivity towards formation of the products of 2-acylation (3-methyl-1H-indol-2-yl)ketones. Other advantages related to this process are the simple work-up procedure and smaller production of chemical waste. The catalyst was easily recycled and reused with a minimal loss in activity through three reaction cycles. The catalyst was characterized by FT-IR spectroscopy, X-Ray diffraction and superficial acidity. Graphical Abstract: [Figure not available: see fulltext.].

Regioselective hydroarylation reactions of C3 electrophilic N-acetylindoles activated by FeCl3: An entry to 3-(Hetero)arylindolines

A method for the direct and rare umpolung of the 3 position of indoles is reported. The activation of N-acetylindole with iron(III) chloride allows the C-H addition of aromatic and heteroaromatic substrates to the C2-C3 double bond of the indole nucleus to generate a quaternary center at C3 and leads regioselectively to 3-arylindolines. Optimization, scope (50 examples), practicability (gram scale, air atmosphere, room temperature), and mechanistic insights of this process are presented. Synthetic transformations of the indoline products into drug-like compounds are also described.