13228-37-0

Basic information

• Product Name: 1H-Indole, 2-butyl-
• CAS NO: 13228-37-0
• Molecular Formula: C12H15N
• Molecular Weight: 173.258
• Mol File: 13228-37-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 2-butyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 2-butyl-(13228-37-0)
• EPA Substance Registry System: 1H-Indole, 2-butyl-(13228-37-0)

Safety Data

• Hazardous Substances Data: 13228-37-0(Hazardous Substances Data)

Upstream product

• 116491-50-0 2-(hex-1-ynyl)aniline 
• 62-53-3 aniline 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 19591-17-4 o-iodoacetanilide 
• 693-02-7 hex-1-yne 
• 104919-72-4 ethyl N-[2-(1-butynyl)phenyl]carbamate 
• 615-43-0 2-iodophenylamine 
• 693-03-8 n-butyl magnesium bromide 
• 13637-43-9 2-methylthioindole 

Downstream Products

• 1357175-01-9 N-((2-butyl-1H-indol-3-yl)(phenyl)methyl)-4-methylbenzenesulfonamide 
• 1304141-54-5 (2R,3R)-(-)-2-butyl-3-benzylindoline 
• 1304141-55-6 (-)-2-butyl-3-(cyclohexylmethyl)indoline 
• 1118030-99-1 2-butyl-3-(phenylthio)-1H-indole 
• 138459-12-8 4'-(2-Butyl-indol-1-ylmethyl)-biphenyl-2-carboxylic acid 

Relevant articles and documents

Synthesis of 2-substituted indoles through cyclization and demethylation of 2-alkynyldimethylanilines by ethanol

Herein, we demonstrated that 2-alkynyldimethylamines easily cyclize in EtOH according to a 5-endo-dig annulation into 2-substituted indoles without the aid of any additives or any metal catalysts to activate the triple bond. Thus, a variety of functionalized 2-styrylindoles, 2-arylindoles, 2-alkynylindoles, and 2-alkylindoles were prepared in high to excellent yields according to an environmentally friendly protocol. The mechanism has been explored to better understand this eco-friendly access to 2-substituted indoles and DFT calculations rationalized the role of the solvent in this N-annulation/dealkylation process.

Gold-catalyzed reactions of 2-alkynyl-phenylamines with α-β-enones

(Chemical Equation Presented) The gold-catalyzed reaction of 2-alkynyl-phenylamines with α,β-enones represents a new general one-pot entry into C-3-alkyl-indoles by sequential reactions. Gold-catalyzed sequential cyclization/ alkylation, N-alkylation/cyclization, or N-alkylation/cyclization/alkylation reactions leading to different indoles can be directed by changing the 2-alkynyl-phenylamine 1/α,β-enone 3 ratio and the reaction temperature. Unusual gold-catalyzed rearrangement reaction of indoles are observed at 140°C. New gold-catalyzed formation of propargyl-alkyl ether under mild conditions and the hydration reaction of N-acetyl-2-ethynyl-phenylamine are reported.

Convenient indole synthesis from ethynylanilines with a polymer-supported fluoride

The cyclization reaction of ethynylanilines having phenyl, alkyl, methoxy, cyano, chloro, and ethoxycarbonyl groups with (polystyrylmethyl)trimethylammonium fluoride in dry MeCN under an argon atmosphere at 100°C proceeded in good yields to give the corresponding indoles without affecting these functional groups. Moreover, the polymer-supported fluoride could be reused for the cyclization reaction when the deprotection reaction of the N-substituted indole with the fluoride ion on resin did not occur under the cyclization conditions.