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

Chemical Properties

clear yellow liquid after melting

Uses

1-Acetylindole may be used in the stereocontrolled synthesis of (±)-geissoschizine. It may be used in the preparation of (1-acetyl-κO-indolyl-κC2)tetracarbonylmanganese, via a standard cyclomanganation procedure.

Synthesis Reference(s)

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

General Description

Quantum chemical calculations of ground state energy, geometrical structure and vibrational wavenumbers of 1-acetylindole has been carried out using density functional (DFT/B3LYP) method. Regioselective acylations of 1-acetylindole (N-acetylindole) under Friedel-Crafts reaction has been reported. Reaction of 1-acetylindole with manganese(III) acetate in the presence of malonic acid, is reported to afford 4-acetyl-3,3a,4,8b-tetrahydro-2H-furo[3,2-b]indol-2-one.

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

Upstream product

• 141-78-6 ethyl acetate 
• 120-72-9 indole 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 1496-76-0 N-benzoylindole 
• 33025-60-4 1-(3-hydroxy-1H-indol-1-yl)ethanone 
• 16800-67-2 N,O-diacetylindoxyl 
• 61403-29-0 N-(2-ethynylphenyl)acetamide 
• 681427-71-4 N-(prop-2'-enyl)-2-vinylacetanilide 
• 26340-49-8 2-iodo-1H-indole 
• 105-36-2 ethyl bromoacetate 
• 99293-86-4 N-acetylindolin-3-ol 
• 7664-93-9 sulfuric acid 
• 83188-11-8 1,4-bis(trimethylsilyl)indole 

Downstream Products

• 15224-25-6 3-benzoylindole 
• 109555-87-5 (1H-indol-3-yl)(naphthalene-1-yl)methanone 
• 91-22-5 quinoline 
• 92013-04-2 1-Acetyl-6-chloroacetylindole 
• 948-65-2 2-phenyl-indole 
• 1204-06-4 trans-3-indole-acrylic acid 

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