17537-64-3

Basic information

• Product Name: 1,3-DIACETYLINDOLE
• Synonyms: 1-(1-ACETYL-1H-INDOL-3-YL)-1-ETHANONE;1,3-DIACETYLINDOLE;1-(1-Acetyl-1H-indol-3-yl)ethanone;1,3-Diacetylindol;1H-Indole, 1,3-diacetyl-;N,3-diacetyl-indole;1,3-diacetyl-1H-indole;1-(1-Acetyl-1H-indol-3-yl)ethan-1-one
• CAS NO: 17537-64-3
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.22
• EINECS: 241-532-5
• Mol File: 17537-64-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 144-147°C
• Boiling Point: 338.8 °C at 760 mmHg
• Flash Point: 158.7 °C
• Appearance: /
• Density: 1.16 g/cm³
• Vapor Pressure: 9.56E-05mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive: Moisture Sensitive
• BRN: 159285
• CAS DataBase Reference: 1,3-DIACETYLINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIACETYLINDOLE(17537-64-3)
• EPA Substance Registry System: 1,3-DIACETYLINDOLE(17537-64-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Safety Statements: 22-24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 17537-64-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 396, 1987 DOI: 10.1055/s-1987-27960

InChI:InChI=1/C12H11NO2/c1-8(14)11-7-13(9(2)15)12-6-4-3-5-10(11)12/h3-7H,1-2H3

Upstream product

• 120-72-9 indole 
• 108-24-7 acetic anhydride 
• 1477-50-5 Indole-2-carboxylic acid 
• 75-36-5 acetyl chloride 
• 88636-48-0 1-acetyl-3-ethylindole 
• 108-05-4 vinyl acetate 
• 703-80-0 3-acetylindole 
• 576-15-8 N-acetylindole 
• 95-20-5 2-methyl-1H-indole 
• 93-97-0 benzoic acid anhydride 
• 64-19-7 acetic acid 

Downstream Products

• 703-80-0 3-acetylindole 
• 4771-10-2 1-(5-nitro-1H-indol-3-yl)ethan-1-one 
• 4993-92-4 3-acetyl-6-nitroindole 
• 16800-68-3 1-acetyl-2,3-dihydro-1H-indol-3-one 
• 83813-66-5 1-acetyl-2-hydroxy-3-indolinone 

Relevant articles and documents

Convenient procedure for dethioketalisation in nitrogen heterocycles

Regeneration of carbonyl compounds from the corresponding thioketals in nitrogen heterocycles have been effected using Dowex 50W acidic catalyst in reasonable yields.

Overcoming Electron-Withdrawing and Product-Inhibition Effects by Organocatalytic Aerobic Oxidation of Alkylpyridines and Related Alkylheteroarenes to Ketones

An organocatalyzed aerobic benzylic C-H oxidation of alkyl and aryl heterocycles has been developed. This transition metal-free method is able to overcome the electron-withdrawing effect as well as product-inhibition effects in heterobenzylic radical oxidation. A variety of ketones bearing N-heterocyclic groups could be prepared under relatively mild conditions with moderate to high yields.

Na 2 CO 3-Catalyzed N-Acylation of Indoles with Alkenyl Carboxylates

The N-acylation of indoles has been accomplished via inorganic base catalysis. It provided an efficient and simple catalysis system for the preparation of N-acylindoles with alkenyl carboxylates as acylating agents. A broad variety of indoles undergo the smooth N-acylation using Na 2 CO 3 as catalyst in MeCN at 120? °C to give the corresponding N-acylindoles in good to excellent yields.

Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream

We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.