134478-87-8

Basic information

• Product Name: 3-methyl-1-(prop-2'-ynyl)indole
• Synonyms: 3-methyl-1-(prop-2'-ynyl)indole
• CAS NO: 134478-87-8
• Molecular Formula: C₁₂H₁₁N
• Molecular Weight: 169.22244
• Mol File: 134478-87-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 294.7±23.0 °C(Predicted)
• Appearance: /
• Density: 0.95±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3-methyl-1-(prop-2'-ynyl)indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-1-(prop-2'-ynyl)indole(134478-87-8)
• EPA Substance Registry System: 3-methyl-1-(prop-2'-ynyl)indole(134478-87-8)

Safety Data

• Hazardous Substances Data: 134478-87-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 1737, 1991 DOI: 10.1016/S0040-4039(00)74317-6

Upstream product

• 83-34-1 3-Methylindole 
• 106-96-7 propargyl bromide 
• 134478-84-5 (2-Bromo-phenyl)-di-prop-2-ynyl-amine 

Relevant articles and documents

Iodonium-Induced Cyclization of N -Allenylindoles and N -Allenylpyrroles: An Access to Iododihydropyrido[1,2- a ]indoles and Dihydroindolizines

The formation of iodinated dihydropyrido[1,2- a ]indoles and dihydroindolizines was achieved by an iodocarbocyclization reaction of N -allenylindoles and N -allenylpyrroles. This transformation proceeded under very mild conditions using N -iodosuccinimide as the electrophilic iodine source to deliver the products via a 6- endo cyclization process. Careful choice of the solvent and concentration were mandatory to obtain the cyclization in good yields.

Tandem Carbenoid C-H Functionalization/Conia-ene Cyclization of N-Propargyl Indoles Generates Pyrroloindoles under Cooperative Rh(II)/Zn(II) Catalysis

The decomposition of diazodicarbonyl compounds in the presence of various metal catalysts has become a reliable method for the functionalization of indoles via carbenoid intermediates. Exploiting the nucleophilic reactivity of the in situ generated malonic ester product formed, we herein report a tandem C-H functionalization/Conia-ene cyclization of N-alkyne tethered indoles. This double functionalization of diazodicarbonyls generates a range of pyrrolo[1,2-a]-, pyrido[1,2-a]-, and azepino[1,2-a]indole products with good synthetic efficiency.

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.