89378-43-8

Basic information

• Product Name: tert-butyl 3-methyl-1H-indole-1-carboxylate
• Synonyms: tert-butyl 3-methyl-1H-indole-1-carboxylate;3-Methyl-1H-indole, N-BOC protected;1-Boc-3-Methylindole
• CAS NO: 89378-43-8
• Molecular Formula: C₁₄H₁₇NO₂
• Molecular Weight: 231
• Mol File: 89378-43-8.mol
• Article Data: 21

Chemical Properties

• Appearance: /
• CAS DataBase Reference: tert-butyl 3-methyl-1H-indole-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 3-methyl-1H-indole-1-carboxylate(89378-43-8)
• EPA Substance Registry System: tert-butyl 3-methyl-1H-indole-1-carboxylate(89378-43-8)

Safety Data

• Hazardous Substances Data: 89378-43-8(Hazardous Substances Data)

Upstream product

• 83-34-1 3-Methylindole 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 6627-89-0 tert-butyl phenyl carbonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 314773-77-8 tert-butyl (2-acetylphenyl)carbamate 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 869852-13-1 tert-butyl 3-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate 
• 1401353-11-4 exo-ethyl-3-methyl-cyclopropa(N-tert.-butoxycarbonyl-2,3-dihydroindole)-2a-carboxylate 
• 1401353-12-5 endo-ethyl-3-methyl-cyclopropa(N-tert.-butoxycarbonyl-2,3-dihydroindole)-2a-carboxylate 
• 623-91-6 diethyl Fumarate 
• 141-05-9 Diethyl maleate 
• 352359-20-7 1-(tert-butoxycarbonyl)-3-methyl-1H-indol-2-ylboronic acid 
• 1616246-76-4 tert-butyl 3-methyl-2-(N-methylphenylsulfonamido)-1H-indole-1-carboxylate 
• 1403665-35-9 methyl 2-(2-(tert-butoxycarbonylamino)phenyl)-2-hydroxypropionate 
• 674819-70-6 1-(1-benzyl-3-methyl-1H-indol-2-yl)-3,4-dihydro-2-naphthalenecarbaldehyde 
• 83-34-1 3-Methylindole 

Relevant articles and documents

A dianionic C3-symmetric scorpionate: Synthesis and coordination chemistry

Introducing charges into ligand systems fine-tunes their electronic properties and influences the solubility of their metal complexes. Herein, we present a synthesis of a dianionic, C3-symmetric ligand combining three anionic N-donors tethered to a positively charged phosphonium center. The tris-skatylmethylphosphonium (TSMP) ligand, isolated in the form of its dipotassium salt TSMPK2, is the first dianionic homoscorpionate capable of metal exchange. The potassium cations in TSMPK2 are exchangeable for other metals, which results in rich coordination chemistry. Thus, the ligand displays a bridging μ2:κ2:κ1 coordination mode with trigonal planar Cu(i) centers in the tetrameric complex [(TSMP)Cu]44-. The κ3 mode is accessed upon addition of 1 equiv. of P(OEt)3 per Cu(i) to yield the tetrahedral monomeric complex [(TSMP)CuP(OEt)3]-. Both Fe(ii) and Ni(ii) in pyridine give octahedral high-spin κ3 complexes with composition (TSMP)M(Py)3 (M = Fe, Ni). Displacement of three pyridine ligands in (TSMP)Fe(Py)3 for a second equivalent of TSMP gives a high-spin pseudotetrahedral 2?:?1 complex [(TSMP)2Fe]2- with the ligands in κ2 coordination mode. The reduction in coordination number is likely due to electrostatic repulsion of the negatively-charged indolides as well as their weaker π-accepting character as compared to pyridine. This journal is

Stereoselective Synthesis of Cyclohepta[b]indoles by Visible-Light-Induced [2+2]-Cycloaddition/retro-Mannich-type Reactions

A novel method for the concise synthesis of cyclohepta[b]indoles in high yields was developed. The method involves a visible-light-induced, photocatalyzed [2+2]-cycloaddition/ retro-Mannich-type reaction of enaminones. Experimental and computational studies suggested that the reaction is a photoredox process initiated by single-electron oxidation of an enaminone moiety, which undergoes subsequent cyclobutane formation and rapidly fragmentation in a radical-cation state to form cyclohepta[b]indoles.

Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes

A new method for the synthesis of bi-heteroaryls is reported, based on the umpolung of indoles with benziodoxol(on)e hypervalent iodine reagents (IndoleBX). The oxidative coupling of IndoleBX with an equimolar amount of electron-rich benzenes, indoles, pyrroles, and thiophenes proceeded under mild transition-metal-free conditions. Functionalized non-symmetrical bi-indolyl heterocycles were accessed efficiently. Introduction of a new type of C2-substituted indole benziodoxole reagents further allowed extending the scope of the reaction to NH unprotected and C3-alkylated indoles. The obtained bi-heterocycles are important building blocks in synthetic and medicinal chemistry, and could be easily transformed into more complex heterocyclic systems.