1914-05-2

Basic information

• Product Name: N-allyl-3-methylindole
• Synonyms: N-allyl-3-methylindole
• CAS NO: 1914-05-2
• Molecular Weight: 171.242
• Mol File: 1914-05-2.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: N-allyl-3-methylindole(CAS DataBase Reference)
• NIST Chemistry Reference: N-allyl-3-methylindole(1914-05-2)
• EPA Substance Registry System: N-allyl-3-methylindole(1914-05-2)

Safety Data

• Hazardous Substances Data: 1914-05-2(Hazardous Substances Data)

Upstream product

• 73396-92-6 2-iodo-N,N-diallylaniline 
• 83-34-1 3-Methylindole 
• 556-56-9 allyl iodid 
• 591-87-7 Allyl acetate 
• 106-95-6 allyl bromide 

Downstream Products

• 83-34-1 3-Methylindole 
• 643-28-7 2-isopropylaniline 
• 1592482-14-8 ((4aS,9aS)-9-allyl-4a-methyl-3-phenyl-4,4a,9,9a-tetrahydro-1H-pyridazino[3,4-b]indol-1-yl)(phenyl)methanone 

Relevant articles and documents

Palladium-catalyzed selective N -allylation of indoles assisted by PEG-water system

The synthesis of N-allylic indoles is of great interest because of their potential biological properties. It is a true challenge to develop new methods for the N-allylation of indoles due to the favorable C3-allylation. We uncovered a new strategy to synthesize N-allylic indoles via a palladium catalyst as a promoting agent, providing the N-allylated indoles in high yields. In addition, the organic reaction with polyethylene glycol (PEG) in water is one of the key emerging strategies that is currently attracting tremendous attention, which is intended to provide alternative eco-friendly and efficient ways for the construction of covalent bonds. In this study, the palladium-catalyzed indoles with allylic acetates in a PEG-water system were investigated under various conditions. This system provides a simple, convenient, and efficient way to afford a high yield of N-allylated indoles.

Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles

Acyloxy-substituted α,β-unsaturated imines generated in situ from triazoles can act as aza-[4 C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system include operational simplicity, readily available substrates, construction of sterically demanding quaternary centers, and convenient derivatization using triflate. (Figure presented.).

Harnessing the Polarizability of Conjugated Alkynes toward [2 + 2] Cycloaddition, Alkenylation, and Ring Expansion of Indoles

Reported is the utilization of electronically biased conjugated alkynes in the development of highly diastereo- and regioselective dearomative [2 + 2] cycloadditions, alkenylations, and ring expansions of electron-rich indoles. Regioselective protonations of cross- and linear-conjugated alkynes were found to be crucial for accessing various cyclobutene-fused indoline and alkenylated indole derivatives. Furthermore, the facile ring expansion of [2 + 2] keto adducts, which were successfully synthesized from ynones, provided 1H-benzo[b]azepine scaffolds.