3-Benzoylindole

Base Information

• Chemical Name: 3-Benzoylindole
• CAS No.: 15224-25-6
• Molecular Formula: C15H11 N O
• Molecular Weight: 221.258
• Hs Code.: 2933990090
• European Community (EC) Number: 239-274-3
• NSC Number: 149903,81264
• UNII: PCO4O32860
• DSSTox Substance ID: DTXSID10164980
• Nikkaji Number: J45.428A
• Wikidata: Q27286482
• ChEMBL ID: CHEMBL1452995
• Mol file: 15224-25-6.mol

Synonyms:3-Benzoylindole;15224-25-6;1H-Indol-3-yl(phenyl)methanone;(1H-Indol-3-yl)-phenyl-methanone;Indole, 3-benzoyl-;3-benzoyl-1H-indole;Ketone, indol-3-yl phenyl;Methanone, 1H-indol-3-ylphenyl-;UNII-PCO4O32860;PCO4O32860;EINECS 239-274-3;NSC-81264;NSC-149903;(1H-Indol-3-yl)(phenyl)methanone;1H-indol-3-yl-phenylmethanone;NSC81264;Oprea1_058429;Oprea1_309632;MLS001181912;SCHEMBL3279652;CHEMBL1452995;DTXSID10164980;HMS1607K12;HMS2853M19;1H-Indol-3-yl(phenyl)methanone #;MFCD00022721;NSC 81264;NSC149903;STK020419;AKOS000111851;CCG-103222;NSC 149903;NCGC00246642-01;AS-36405;SMR000567726;CS-0320898;FT-0655395;A921113;SR-01000389850;SR-01000389850-1;BRD-K67717745-001-07-9;Q27286482

Chemical Property of 3-Benzoylindole

Chemical Property:

• Vapor Pressure: 2.48E-07mmHg at 25°C
• Melting Point: 170 °C
• Boiling Point: 422.1°Cat760mmHg
• PKA: 15.55±0.30(Predicted)
• Flash Point: 214.9°C
• PSA: 32.86000
• Density: 1.229g/cm³
• LogP: 3.39890
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 221.084063974
• Heavy Atom Count: 17
• Complexity: 283

Purity/Quality:

97% ^*data from raw suppliers

3-Benzoylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C2=CNC3=CC=CC=C32
• General Description: 3-Benzoylindole is a 3-substituted indole derivative characterized by a benzoyl (phenyl ketone) group at the 3-position of the indole ring. It reacts efficiently with sodium naphthalenide, a single electron transfer (SET) reagent, due to the electron-withdrawing nature of the benzoyl group, which lowers the LUMO energy of the indole ring and facilitates electron transfer. This reaction yields a single product selectively and in high yield, demonstrating its utility in the synthesis of indole derivatives via SET chemistry.

Technology Process of 3-Benzoylindole

There total 85 articles about 3-Benzoylindole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3-(N-methyl-benzenecarboximidoyl)indole hydrogen tetrafluoroborate → 3-benzoylindole (15224-25-6)

Guidance literature:

With water; sodium acetate; for 0.166667h; Reflux;

DOI:10.1016/j.tet.2015.05.005

Reference yield: 98.0%

3-benzyl-1H-indole (16886-10-5) → 3-benzoylindole (15224-25-6)

Guidance literature:

With tert.-butylnitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; at 20 ℃; for 15h; Irradiation;

DOI:10.1002/cctc.201600704

Reference yield: 97.0%

N-benzoylindole (1496-76-0) → 3-benzoylindole (15224-25-6)

Guidance literature:

With aluminum oxide; In neat (no solvent); at 100 ℃; for 0.0666667h; Microwave irradiation; Green chemistry;

DOI:10.1039/c3nj00854a

upstream raw materials:

indole

ethylmagnesium bromide

N,N-dimethylbenzamide

2-Ethoxy-2-phenyl-1,3-dioxolane

Downstream raw materials:

3-benzoyl-1-methylindole

2-(3-phenyl-1⁽²⁾H-pyrazol-4-yl)-aniline

2-cyano-3-(α-phenyl)indoleacetonitrile

3-benzoyl-1-diethylphosphonoindole

Refernces

Effect of sodium naphthalenide, a key set reagent, on 3-substituted indoles

10.3987/COM-04-10142

The research investigates the effects of sodium naphthalenide, a single electron transfer (SET) reagent, on 3-substituted indoles to explore the synthesis of indole derivatives through SET reactions. The study found that indoles with electron-donating substituents do not react with sodium naphthalenide, while those with electron-withdrawing substituents readily undergo reactions, yielding various products depending on the specific substituent. For instance, 3-trifluoroacetylindole, 3-acetylindole, and 3-benzoylindole each produced a single product, whereas 3-formylindole generated four products. The reactions involving electron-withdrawing groups were highly selective and efficient, with high yields of the desired products. The study concludes that SET reactions with sodium naphthalenide are an effective method for constructing indole derivatives when electron-withdrawing substituents are present on the indole ring, as these groups lower the LUMO energy of the indole ring, facilitating electron transfer from the reagent to the substrate.

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