53000-40-1

Basic information

• Product Name: 3-Indolylphenyliodonium betaine
• Synonyms: 3-Indolylphenyliodonium betaine
• CAS NO: 53000-40-1
• Molecular Weight: 319.145
• Mol File: 53000-40-1.mol

Chemical Properties

• CAS DataBase Reference: 3-Indolylphenyliodonium betaine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Indolylphenyliodonium betaine(53000-40-1)
• EPA Substance Registry System: 3-Indolylphenyliodonium betaine(53000-40-1)

Safety Data

• Hazardous Substances Data: 53000-40-1(Hazardous Substances Data)

Upstream product

• 120-72-9 indole 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Downstream Products

• 95873-88-4 3-Indolylphenyliodonium Bromide 
• 112890-09-2 phenyl β-(N-benzenesulfonylindolyl)iodonium chloride 
• 591-50-4 iodobenzene 
• 16886-09-2 3-allylindole 
• 83-34-1 3-Methylindole 
• 16863-96-0 3-chloro-1H-indole 
• 65610-58-4 1-Methyl-2-chloroindole 
• 1484-27-1 3-bromoindole 
• 80786-82-9 (1-Methyl-3-indolyl)phenyliodonium Methosulfate 
• 7135-34-4 1-benzyl-2-chloro-indole 

Relevant articles and documents

A NEW CARBON-CARBON BOND FORMING REACTION IN INDOLE CHEMISTRY. C3-ARYLATION AND ALKYLATION WITH PHENYL (β-INDOLYL)IODONIUM TRIFLUOROACETATE

Phenyl(β-indolyl)iodonium trifuoroacetate was reacted with various alkyl and aryllithiums (CH3, n-C4H9, C3H5, C6H5) in BF3Et2O/THF to yield C3-alkylation and arylation of the indole nucleus with reductive elimination of iodobenzene.

Copper(I)-Catalyzed Asymmetric Dearomatization of Indole Acetamides with 3-Indolylphenyliodonium Salts

The rapid and direct asymmetric synthesis of 3-(3a-indolyl)hexahydropyrroloindoline motifs is an extremely important part of the total synthesis of several alkaloid structures. Herein, an intermolecular, asymmetric cascade dearomatization reaction of indole acetamides with 3-indolylphenyliodonium salts has been developed. This protocol provides a straightforward access to 3-(3a-indolyl)hexahydropyrroloindolines bearing an all-carbon quaternary stereocenter at the C3 position of the indoline ring with high enantioselectivities. The utility of the protocol has been demonstrated by the formal asymmetric synthesis of folicanthine.

Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung

The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 °C and were applied in the C?H arylation of unactivated arenes using either rhodium or ruthenium catalysts. A broad range of heterocyclic systems of high interest for synthetic and medicinal chemistry was accessed in high yields. The developed C?H functionalization could not be achieved using reported reagents or methods, highlighting the unique reactivity of Indole- and Pyrrole-BX.