85992-59-2

Basic information

• Product Name: 1-(1-methyl-1H-indol-3-yl)-2-phenylethanone
• Synonyms: 1-(1-methyl-1H-indol-3-yl)-2-phenylethanone
• CAS NO: 85992-59-2
• Molecular Formula: C₁₇H₁₅NO
• Molecular Weight: 249.3071
• Mol File: 85992-59-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(1-methyl-1H-indol-3-yl)-2-phenylethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-methyl-1H-indol-3-yl)-2-phenylethanone(85992-59-2)
• EPA Substance Registry System: 1-(1-methyl-1H-indol-3-yl)-2-phenylethanone(85992-59-2)

Safety Data

• Hazardous Substances Data: 85992-59-2(Hazardous Substances Data)

Upstream product

• 603-76-9 1-methylindole 
• 3389-53-5 phenylacetylpyrrolidine 
• 103-80-0 phenylacetyl chloride 
• 140-29-4 phenylacetonitrile 
• 96694-00-7 1-methyl-3-trimethylsilylindole 

Downstream Products

• 85992-56-9 1-(1-Methyl-1H-indol-3-yl)-2-phenyl-ethanone oxime 

Relevant articles and documents

New Friedel-Crafts strategy for preparing 3-acylindoles

A selective Friedel-Crafts acylation of indoles via an unusual cleavage of the amide C-N bond was achieved by triflic anhydride activation. This method offers rapid efficient access to high-biological-value 3-acylindoles, performs a series of scrupulous mechanistic studies and offers a strong courage that amide synthons can form new C-C bonds under transition-metal-free conditions.

A new methodology for functionalization at the 3-position of indoles by a combination of boron lewis acid with nitriles

We discovered that a reagent comprising a combination of PhBCl2 and nitriles was useful for syntheses of both 3-acylindoles and 1-(1H-indol-3-yl)alkylamine from indoles. The reaction proceeded selectively at the 3-position of indoles providing 3-acylindoles in moderate to high yields on treatment with the above reagent. Furthermore, the reaction provided the corresponding amine products in moderate to high yields after the intermediate imine was reduced by NaBH3CN. These reactions proceeded under mild conditions and are applicable to the formation of indoles functionalized at the 3-position.

An New Method for the Synthesis of 3-Substituted Indoles by ipso-Substitution

Acylation of 3-(trimethylsilyl)-indole 1a with acylhalides 2 affords 3-acylindoles 4. 3-(Trimethylsilyl)-indoles 1a, b react with Michael-acceptors 5 and 8 in presence of Lewis acids to yield the 3-substituted indoles 6, 9, and 10.