15224-25-6

Basic information

• Product Name: 3-benzoylindole
• Synonyms: 3-benzoylindole;1H-Indol-3-ylphenyl ketone;3-Benzoyl-1H-indole;Phenyl(1H-indole-3-yl) ketone
• CAS NO: 15224-25-6
• Molecular Formula: C₁₅H₁₁NO
• Molecular Weight: 221.25394
• EINECS: 239-274-3
• Mol File: 15224-25-6.mol
• Article Data: 69

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 422.1°Cat760mmHg
• Flash Point: 214.9°C
• Appearance: /
• Density: 1.229g/cm³
• Vapor Pressure: 2.48E-07mmHg at 25°C
• Refractive Index: 1.683
• PKA: 15.55±0.30(Predicted)
• CAS DataBase Reference: 3-benzoylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzoylindole(15224-25-6)
• EPA Substance Registry System: 3-benzoylindole(15224-25-6)

Safety Data

• Hazardous Substances Data: 15224-25-6(Hazardous Substances Data)

Usage

General Description

3-benzoylindole is an organic chemical compound classified under the family of indoles, which are heterocyclic aromatic compounds. 3-benzoylindole has a benzoyl side chain attached to the indole core at the 3-position, hence the name 3-benzoylindole. The molecular formula of 3-benzoylindole is C15H11NO. It has potential applications in fields such as organic chemistry, pharmaceutical chemistry and materials science, such as the synthesis of various medical drugs, dyes and plastics. However, the detailed properties of 3-benzoylindole, such as its toxicity, biological activity or environmental behavior, are not well-studied and caution should be exercised when handling this compound.

InChI:InChI=1/C15H11NO/c17-15(11-6-2-1-3-7-11)13-10-16-14-9-5-4-8-12(13)14/h1-10,16H

Upstream product

• 120-72-9 indole 
• 925-90-6 ethylmagnesium bromide 
• 611-74-5 N,N-dimethylbenzamide 
• 19798-74-4 2-Ethoxy-2-phenyl-1,3-dioxolane 
• 98-88-4 benzoyl chloride 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 80360-19-6 phenyl(1-(phenylsulfonyl)-1H-indol-3-yl)methanone 
• 33268-96-1 3-benzoylindole-2-carboxylic acid 
• 111122-98-6 3-(2-Phenyl-benzo[1,3]oxathiol-2-yl)-1H-indole 
• 82414-15-1 3-Phenyl-3a,8a-dihydro-isoxazolo[5,4-b]indole-8-carboxylic acid ethyl ester 
• 102652-00-6 (3-Indolyl)methoxyphenylcarbenium-tetrafluoroborat 
• 81581-98-8 1-[3-Acetyl-2-(1H-indol-3-yl)-2-phenyl-imidazolidin-1-yl]-ethanone 
• 153942-75-7 [1-(tert-Butyl-dimethyl-silanyl)-1H-indol-3-yl]-phenyl-methanone 
• 91477-18-8 N-methoxycarbonyl-3-benzoylindole 

Downstream Products

• 19012-01-2 3-benzoyl-1-methylindole 
• 111562-63-1 2-(3-phenyl-1⁽²⁾H-pyrazol-4-yl)-aniline 
• 109678-22-0 2-cyano-3-(α-phenyl)indoleacetonitrile 
• 109662-80-8 3-benzoyl-1-diethylphosphonoindole 
• 109662-81-9 1-cyano-1-diethylphosphono-3-(α-phenyl)indoleacetonitrile 
• 91477-16-6 N-ethoxycarbonyl-3-benzoylindole 
• 67060-92-8 (1H-indole-1,3-diyl)bis(phenylmethanone) 
• 120-72-9 indole 
• 94-33-7 C₉H₁₀O₃ 
• 91477-18-8 N-methoxycarbonyl-3-benzoylindole 
• 91477-17-7 phenyl(1-tosyl-1H-indol-3-yl)methanone 
• 607-28-3 (E)-1H-indole-2,3-dione 3-oxime 
• 82414-25-3 3-benzoylindole, Z-oxime 
• 85729-25-5 N-(1H-indol-3-yl)benzamide 

Relevant articles and documents

A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride.

[reaction--see text] Indoles are selectively acylated at the 3-position in high yields on treatment with a wide variety of acyl chlorides in CH(2)Cl(2) in the presence of diethylaluminum chloride or dimethylaluminum chloride. The reaction proceeds under mild conditions and is applicable to indoles bearing various functional groups without NH protection.

The Reactions of Electron-Rich Heterocycles with Derivatives of Orthocarboxylic Acids; VIII. Proton Acid-Catalyzed Acylation of Indoles by 2-Alkoxy-1,3-dioxolanes

In acid-catalyzed reactions with 3-unsubstituted indoles 1, 2-alkoxy-1,3-dioxolanes 2a-c behave as acyl equivalents.Depending on the substitution patterns of the reaction partners, the 1,3-dioxolanium ions 3a-c, generated in situ from the cyclic ortho esters by the action of sulfosalicylic acid, react to form tris-(3-indolyl)alkanes 6 and 9, bis-(3-indolyl)ethenes 7, or 3-benzoylindoles 8.Analogous reactivity was observed with related acyclic ortho esters.

A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study

Novel and efficient Mn(OAc)3?2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.

METHODS OF TREATING CANCER

The present disclosure relates to methods of treating cancer in a patient using a combination of an inhibitor of an immune checkpoint protein and an indole compound or its phosphate derivative.

Synthesis of 3-acylindoles: via copper-mediated oxidative decarbethoxylation of ethyl arylacetates

An efficient regioselective C-3 acylation of free indoles (N-H) has been accomplished via oxidative decarbethoxylation of easily available ethyl arylacetates using Cu(OAc)2 and KOtBu in DMSO.