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

• 108-05-4 vinyl acetate 
• 1795-83-1 N-Phenylacetohydroxamic acid 
• 614-76-6 N-acetyl-2-bromoaniline 
• 120-72-9 indole 
• 75-36-5 acetyl chloride 
• 141-78-6 ethyl acetate 
• 108-24-7 acetic anhydride 
• 872-36-6 vinylene carbonate 
• 103-84-4 Acetanilid 
• 110598-59-9 N-acetyl-2-<(trimethylsilyl)ethynyl>aniline 
• 19591-17-4 o-iodoacetanilide 
• 108-22-5 Isopropenyl acetate 
• 16800-67-2 N,O-diacetylindoxyl 
• 33025-60-4 1-(3-hydroxy-1H-indol-1-yl)ethanone 

Downstream Products

• 91-22-5 quinoline 
• 259103-67-8 methyl 1-benzyl-4-[2-(1-indolyl)-2-oxoethyl]-1,4-dihydropyridine-3(E)-acrylate 
• 92013-04-2 1-Acetyl-6-chloroacetylindole 
• 1224728-88-4 C₁₈H₁₇NO₃ 
• 1224728-85-1 C₁₈H₁₇NO₂ 
• 1224728-90-8 C₁₇H₁₄BrNO₂ 
• 1224728-91-9 C₁₇H₁₄INO₂ 
• 1224728-87-3 C₂₁H₂₃NO₂ 
• 1224728-80-6 1-(3-(4-methoxyphenyl)-1H-indol-1-yl)ethan-1-one 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 1224728-89-5 C₁₈H₁₇NO₃ 
• 1224728-86-2 C₁₈H₁₇NO₂ 
• 1403485-64-2 1-(2-phenethyl-1H-indol-1-yl)ethanone 
• 1403485-65-3 1-(2-(4-methoxyphenethyl)-1H-indol-1-yl)ethanone 

Relevant articles and documents

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