576-15-8

Basic information

• Product Name: 1-ACETYLINDOLE
• Synonyms: 1-ACETYLINDOLE;N-ACETYLINDOLE;1-acetyl-1h-indol;Acetylindole;1-acetyl-1H-indole;L-Acetylindole;1H-Indole, 1-acetyl- (9CI);1H-Indole, 1-acetyl-
• CAS NO: 576-15-8
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: 209-396-1
• Product Categories: ACETYLGROUP;Indoles and derivatives;Indole;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 576-15-8.mol
• Article Data: 67

Chemical Properties

• Melting Point: 189 °C
• Boiling Point: 123-125 °C8 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear to light yellow liquid.
• Density: 1.387 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0111mmHg at 25°C
• Refractive Index: n20/D 1.607(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-ACETYLINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETYLINDOLE(576-15-8)
• EPA Substance Registry System: 1-ACETYLINDOLE(576-15-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 576-15-8(Hazardous Substances Data)

Usage

Description

1-Acetylindole, also known as N-acetylindole, is an organic compound with the molecular formula C9H7NO. It is a clear yellow liquid after melting and has been the subject of quantum chemical calculations to determine its ground state energy, geometrical structure, and vibrational wavenumbers using the density functional (DFT/B3LYP) method. 1-Acetylindole is known for its regioselective acylations under Friedel-Crafts reaction conditions and has been reported to react with manganese(III) acetate in the presence of malonic acid to afford 4-acetyl-3,3a,4,8b-tetrahydro-2H-furo[3,2-b]indol-2-one.

Uses

1. Used in Organic Synthesis:
1-Acetylindole is used as a synthetic intermediate for the stereocontrolled synthesis of (±)-geissoschizine, a naturally occurring alkaloid with potential biological activities. Its unique structure and reactivity make it a valuable building block in the development of novel compounds with various applications.
2. Used in Coordination Chemistry:
In the field of coordination chemistry, 1-Acetylindole is used in the preparation of (1-acetyl-κO-indolyl-κC2)tetracarbonylmanganese through a standard cyclomanganation procedure. This application highlights its utility in the formation of metal complexes, which can have potential uses in catalysis, materials science, and other areas of chemistry.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 2151, 1988 DOI: 10.1016/S0040-4039(00)86696-4

InChI:InChI=1/C10H9NO/c1-8(12)11-7-6-9-4-2-3-5-10(9)11/h2-7H,1H3

Upstream product

• 120-72-9 indole 
• 108-24-7 acetic anhydride 
• 141-78-6 ethyl acetate 
• 593-60-2 Vinyl bromide 
• 61403-29-0 N-(2-ethynylphenyl)acetamide 
• 496-15-1 1-indoline 
• 64-19-7 acetic acid 
• 3972-52-9 2-deuterio-1H-indole 
• 1403486-00-9 C₁₀H₈⁽²⁾HNO 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 140-88-5 ethyl acrylate 
• 108-05-4 vinyl acetate 
• 872-36-6 vinylene carbonate 
• 103-84-4 Acetanilid 

Downstream Products

• 15224-25-6 3-benzoylindole 
• 109555-87-5 (1H-indol-3-yl)(naphthalene-1-yl)methanone 
• 184476-69-5 2-(3-Acetyl-1-benzyl-1,4-dihydro-pyridin-4-yl)-1-indol-1-yl-ethanone 
• 185824-03-7 methyl 4-[2-(1-indolyl)-2-oxoethyl]-1-[2-(phenylsulfanyl)ethyl]-1,4-dihydro-pyridine-3(E)-acrylate 
• 91-22-5 quinoline 
• 92013-04-2 1-Acetyl-6-chloroacetylindole 
• 78388-91-7 1-(2-phenylindol-1-yl)ethanone 
• 54470-44-9 1-(3-phenyl-1H-indol-1-yl)ethan-1-one 
• 16800-68-3 1-acetyl-2,3-dihydro-1H-indol-3-one 
• 1038864-39-9 1-acetylindole-2-pentafluorobenzene 
• 91-56-5 indole-2,3-dione 
• 1235306-79-2 3-(2'-nitrophenyl)-N-acetylindole 

Relevant articles and documents

Synthesis and characterization of Trichloroisocyanouric acid functionalized mesoporous silica nanocomposite (SBA/TCCA) for the Acylation of Indole

Trichloroisocyanouric acid (TCCA)-functionalized mesoporous silica nanocomposites (SBA/ TCCA) were synthesized and characterized for the acylation of indole. The uniform incorporation of TCCA inside the SBA-15 matrix was confirmed by standard characteriza

An efficient catalytic method for the c-n acylation of heterocycles by schiff base co(Ii), ni(ii), cu(ii) and zn(ii) transition metal complexes

The catalytic activity of Schiff base Co(II), Ni(II), Cu(II) and Zn(II) transition metal complexes was tested for N-Acylation of heterocycles with acetyl chloride. It is observed that all the complexes worked as efficient catalysts. The structural type of complexes was studied by an X-ray powder diffractogram (XRD). The mixed ligand complexes with PPh3 ligand show greater activity as compared to Phen complexes and Schiff base complexes. Especially complex [Ni(L)(PPh3)2Cl2] efficiently worked as a catalyst because of high thermal stability (TGA-DSC) and large catalytic surface area (BET).

Ascorbic Acid as an Aryl Radical Inducer in the Gold-Mediated Arylation of Indoles with Aryldiazonium Chlorides

In recent years interest in the development of protocols that facilitate the oxidative addition of gold to access mild cross-coupling processes mediated by this metal has increased. In this context, we report herein that ascorbic acid, a natural and readily accessible antioxidant, can be used to accelerate the oxidative addition of aryldiazonium chlorides onto AuI. The aryl–AuIII species generated in this way, has been used to prepare 3-arylindoles in a one-pot protocol starting from anilines and para-, meta-, and ortho- substituted aryldiazonium chlorides. The mechanism underlying the oxidative addition has been examined in detail based on EPR analyses, cyclic voltammetry, and DFT calculations. Interestingly, we have found that in this protocol, the chloride atom induces the AuII/AuIII oxidation step.

Aerobic oxidative dehydrogenation of N-heterocycles over OMS-2-based nanocomposite catalysts: Preparation, characterization and kinetic study

OMS-2-based nanocomposites doped with tungsten were prepared for the first time and their remarkably enhanced catalytic activity and recyclability in aerobic oxidative dehydrogenation of N-heterocycles were examined in detail. Many tetrahydroquinoline derivatives and a broad range of other N-heterocycles could be tolerated by the catalytic system using a biomass-derived solvent as a reaction medium. Newly generated mixed crystal phases, noticeably enhanced surface areas and labile lattice oxygen of the OMS-2-based nanocomposite catalysts might contribute to their excellent catalytic performance. Moreover, a kinetic study was extensively performed which concluded that the dehydrogenation of 1,2,3,4-tetrahydroquinoline is a first-order reaction, and the apparent activation energy is 29.66 kJ mol-1