22582-67-8

Basic information

• Product Name: 1-(1H-indol-3-yl)butan-1-one
• Synonyms: 1-(1H-Indol-3-yl)-1-butanone;1-(1H-indol-3-yl)-1-butanone(SALTDATA: FREE);3-BUTYRYLINDOLE
• CAS NO: 22582-67-8
• Molecular Formula: C₁₂H₁₃NO
• Molecular Weight: 187.2377
• EINECS: 245-103-3
• Mol File: 22582-67-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 169 °C
• Boiling Point: 354.1°Cat760mmHg
• Flash Point: 175.8°C
• Appearance: /
• Density: 1.125g/cm³
• Vapor Pressure: 3.42E-05mmHg at 25°C
• Refractive Index: 1.611
• PKA: 15.54±0.30(Predicted)
• CAS DataBase Reference: 1-(1H-indol-3-yl)butan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1H-indol-3-yl)butan-1-one(22582-67-8)
• EPA Substance Registry System: 1-(1H-indol-3-yl)butan-1-one(22582-67-8)

Safety Data

• Hazardous Substances Data: 22582-67-8(Hazardous Substances Data)

Usage

General Description

1-(1H-indol-3-yl)butan-1-one, also known as 3-indolebutyrylketone, is a chemical compound with the molecular formula C12H13NO. It is a ketone derivative of indole, which is a heterocyclic aromatic organic compound. This chemical is commonly used in the synthesis of pharmaceuticals and is a key intermediate in the production of various substances such as tryptophan metabolites and indole alkaloids. Its structure contains both an indole ring and a ketone group, making it a valuable building block in organic chemistry for the creation of complex molecules. Additionally, it has potential applications in the field of medicinal chemistry and drug development due to its unique structural features.

InChI:InChI=1/C12H13NO/c1-2-5-12(14)10-8-13-11-7-4-3-6-9(10)11/h3-4,6-8,13H,2,5H2,1H3

Upstream product

• 120-72-9 indole 
• 109-74-0 propyl cyanide 
• 106-31-0 butanoic acid anhydride 
• 141-75-3 butyryl chloride 

Downstream Products

• 111356-25-3 2-(3-propyl-1⁽²⁾H-pyrazol-4-yl)-aniline 
• 405275-54-9 1-(4-chlorobenzyl)-3-(1-hydroxybutyl)-1H-indole 
• 558469-95-7 3-butyryl-1-(4-chlorobenzyl)-1H-indole 

Relevant articles and documents

THE ANTICONVULSANT ACTIVITY OF 3-ACYLINDOLES COMPARED WITH

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Br?nsted acidic ionic liquid-promoted direct C3-acylation of: N -unsubstituted indoles with acid anhydrides under microwave irradiation

A green and efficient pathway for the synthesis of 3-acylindoles using a Br?nsted acidic ionic liquid as a catalyst has been developed for the first time. The C3-acylation of N-unsubstituted indoles with acid anhydrides affords the desired products in good to excellent yields with high regioselectivity under microwave irradiation. Moreover, the Br?nsted acidic ionic liquid can be recycled up to four times without significant loss of catalytic activity.

A simple, effective, green method for the regioselective 3-acylation of unprotected indoles

A fast and green method is developed for regioselective acylation of indoles in the 3-position without the need for protection of the NH position. The method is based on Friedel-Crafts acylation using acid anhydrides. The method has been optimized, and Y(OTf)3 in catalytic amounts is found to be the best catalyst together with the commercially available ionic liquid [BMI]BF4 (1-butyl-3-methylimidazolium tetrafluoro-borate) as solvent. The reaction is completed in a very short time using monomode microwave irradiation. The catalyst can be reused up to four times without significant loss of activity. A range of substituted indoles are investigated as substrates, and thirteen new compounds have been synthesized.