5541-89-9

Basic information

• Product Name: 4-(1H-INDOL-3-YL)BUTAN-2-ONE
• Synonyms: CHEMBRDG-BB 4003908;1-(INDOL-3-YL)BUTAN-3-ONE;4-(1H-INDOL-3-YL)BUTAN-2-ONE;4-(1H-indol-3-yl)butan-2-one(SALTDATA: FREE);3-(3-Oxobutyl)-1H-indole;4-(1H-Indol-3-yl)butan-2-one 95%
• CAS NO: 5541-89-9
• Molecular Formula: C₁₂H₁₃NO
• Molecular Weight: 187.24
• Product Categories: Building Blocks;C12;Chemical Synthesis;Heterocyclic Building Blocks;Indoles
• Mol File: 5541-89-9.mol
• Article Data: 95

Chemical Properties

• Melting Point: 94 °C
• Boiling Point: 356.1 °C at 760 mmHg
• Flash Point: 177 °C
• Appearance: /
• Density: 1.136 g/cm³
• Vapor Pressure: 2.98E-05mmHg at 25°C
• Refractive Index: 1.613
• PKA: 17.13±0.30(Predicted)
• CAS DataBase Reference: 4-(1H-INDOL-3-YL)BUTAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1H-INDOL-3-YL)BUTAN-2-ONE(5541-89-9)
• EPA Substance Registry System: 4-(1H-INDOL-3-YL)BUTAN-2-ONE(5541-89-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 5541-89-9(Hazardous Substances Data)

Usage

General Description

4-(1H-INDOL-3-YL)BUTAN-2-ONE is a chemical compound also known by the name indole-3-butan-2-one. It is a ketone derivative of indole, a heterocyclic aromatic organic compound. This chemical has a molecular formula of C12H13NO and a molar mass of 187.24 g/mol. It is commonly used in organic synthesis and as a building block for the preparation of various pharmaceuticals and natural products. Additionally, 4-(1H-INDOL-3-YL)BUTAN-2-ONE has been researched for its potential biologically active properties and its role in the synthesis of various bioactive molecules.

InChI:InChI=1/C12H13NO/c1-9(14)6-7-10-8-13-12-5-3-2-4-11(10)12/h2-5,8,13H,6-7H2,1H3

Upstream product

• 120-72-9 indole 
• 78-94-4 methyl vinyl ketone 
• 106462-95-7 (E)-4-(1-methoxy-1H-indol-3-yl)but-3-en-2-one 
• 860360-21-0 2-(1H-indol-3-ylmethyl)-3-oxo-butyric acid 
• 764-01-2 methyl propargyl alcohol 
• 2028-63-9 but-3-yn-2-ol 
• 598-32-3 2-hydroxy-3-butene 
• 100956-30-7 ethyl 2-((1H-indol-3-yl)methyl)-3-oxobutanoate 
• 487-89-8 Indole-3-carboxaldehyde 
• 67-64-1 acetone 
• 496-15-1 1-indoline 
• 590-90-9 1-Hydroxy-3-butanone 
• 31951-75-4 4-(1H-indol-3-yl)-but-3-en-2-one 
• 98-95-3 nitrobenzene 

Downstream Products

• 573711-01-0 toluene-4-sulfonic acid 3-(1H-indol-3-yl)-1-methyl-propyl ester 
• 18992-67-1 1,2-dimethyl-9H-carbazole 
• 15467-30-8 3-(1H-indol-3-yl)-1-methyl-propylamine 
• 14105-23-8 4-(1H-indol-3-yl)butan-2-one oxime 
• 666177-56-6 3',4'-dihydro-2-hydroxy-5'-methyl-1-pentafluorobenzoylspiro[indoline-3',2-[2H]pyrrole] 
• 666177-55-5 C₁₉H₁₂ClF₅N₂O 

Relevant articles and documents

Clay (Montmorillonite K10) catalysis of the Michael addition of α,β-unsaturated carbonyl compounds to indoles: The beneficial role of alcohols

The Michael addition of methylvinylketone to indole can be performed under smooth conditions by running the reaction in the presence of an acidic clay catalyst (K10 Montmorillonite) and an aliphatic alcohol such as ethanol or 2-propanol. Presence of an alcohol along with a polar solvent (nitromethane) in the reaction medium considerably improves the reaction.

Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis

We report the design of a bifunctional metal–organic layer (MOL), Hf12-Ru-Co, composed of [Ru(DBB)(bpy)2]2+ [DBB-Ru, DBB=4,4′-di(4-benzoato)-2,2′-bipyridine; bpy=2,2′-bipyridine] connecting ligand as a photosensitizer and Co(dmgH)2(PPA)Cl (PPA-Co, dmgH=dimethylglyoxime; PPA=4-pyridinepropionic acid) on the Hf12 secondary building unit (SBU) as a hydrogen-transfer catalyst. Hf12-Ru-Co efficiently catalyzed acceptorless dehydrogenation of indolines and tetrahydroquinolines to afford indoles and quinolones. We extended this strategy to prepare Hf12-Ru-Co-OTf MOL with a [Ru(DBB)(bpy)2]2+ photosensitizer and Hf12 SBU capped with triflate as strong Lewis acids and PPA-Co as a hydrogen transfer catalyst. With three synergistic active sites, Hf12-Ru-Co-OTf competently catalyzed dehydrogenative tandem transformations of indolines with alkenes or aldehydes to afford 3-alkylindoles and bisindolylmethanes with turnover numbers of up to 500 and 460, respectively, illustrating the potential use of MOLs in constructing novel multifunctional heterogeneous catalysts.

Boron-Catalyzed Dehydrative Friedel-Crafts Alkylation of Arenes Using β-Hydroxyl Ketone as MVK Precursor

Boron-catalyzed environmentally benign dehydrative Friedel-Crafts alkylation of indole/pyrrole and aniline derivatives with β-hydroxyl ketones has been developed for the first time. This method provides an efficient and green replacement of toxic and unst