99275-47-5

Basic information

• Product Name: 1-BOC-5-METHOXYINDOLE
• Synonyms: N-BOC-5-METHOXYINDOLE;TERT-BUTYL 5-METHOXY-1H-INDOLE-1-CARBOXYLATE;1-BOC-5-METHOXYINDOLE;5-Methoxy-1H-indole, N-BOC protected;5-Methoxy-1H-indole, N-BOC protected 98%;N-(tert-Butoxycarbonyl)-5-methoxyindole;5-Methoxyindole-1-carboxylic acid tert-butyl ester;5-Methoxy-1H-indole,N-BOCprotected98%
• CAS NO: 99275-47-5
• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.29
• Product Categories: blocks;IndolesOxindoles;Indoline & Oxindole;Building Blocks;C13 to C27;Chemical Synthesis;Heterocyclic Building Blocks;Indoles
• Mol File: 99275-47-5.mol
• Article Data: 23

Chemical Properties

• Melting Point: 82-85
• Boiling Point: 357.34 °C at 760 mmHg
• Flash Point: 169.913 °C
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: Keep Cold
• CAS DataBase Reference: 1-BOC-5-METHOXYINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BOC-5-METHOXYINDOLE(99275-47-5)
• EPA Substance Registry System: 1-BOC-5-METHOXYINDOLE(99275-47-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 99275-47-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 99275-47-5 differently. You can refer to the following data:
1. Reactant for preparation of:? ;Asymmetric intramolecular Friedel-Crafts alkylation reaction1? ;Palladium-catalyzed carboaminoxylations with arylboronic acids and TEMPO catalyst2? ;Fluorescent pyrimidopyrimidoindole nucleosides via Suzuki-Miyaura coupling reaction3? ;Novel conformationally restricted β- and γ-amino acids4? ;2-(Indolyl) borates, silanes, and silanols5? ;DNA minor groove alkylating agents as stable amine-based prodrugs designed for tumor-specific release6
2. Reactant for preparation of:Asymmetric intramolecular Friedel-Crafts alkylation reactionPalladium-catalyzed carboaminoxylations with arylboronic acids and TEMPO catalystFluorescent pyrimidopyrimidoindole nucleosides via Suzuki-Miyaura coupling reactionNovel conformationally restricted β- and γ-amino acids2-(Indolyl) borates, silanes, and silanolsDNA minor groove alkylating agents as stable amine-based prodrugs designed for tumor-specific release

InChI:InChI=1/C14H17NO3/c1-14(2,3)18-13(16)15-8-7-10-9-11(17-4)5-6-12(10)15/h5-9H,1-4H3

Upstream product

• 1006-94-6 5-methoxylindole 
• 13303-10-1 tert-Butyl 4-nitrophenyl carbonate 
• 930-29-0 1-chlorocyclopent-1-ene 
• 290331-71-4 1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid 
• 75-07-0 acetaldehyde 
• 192189-10-9 3-iodo-5-methoxyindole-1-carboxylic acid tert-butyl ester 
• 100-52-7 benzaldehyde 
• 110-62-3 pentanal 
• 102-50-1 2-methyl-4-methoxyaniline 
• 129822-42-0 N-(tert-butoxycarbonyl)-4-methoxy-2-methylaniline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 157496-75-8 tert-butyl (2-iodo-4-methoxyphenyl)carbamate 
• 138344-11-3 2-Hydroxy-5-methoxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 

Downstream Products

• 10371-86-5 9-methoxyellipticine 
• 1256359-99-5 tert-butyl 5-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole-1-carboxylate 
• 906779-78-0 2-(3-chlorophenyl)-5-methoxy-1H-indole 
• 290331-71-4 1-(tert-butoxycarbonyl)-5-methoxy-1H-indol-2-ylboronic acid 
• 7699-18-5 5-methoxyindolin-2-one 
• 1006-94-6 5-methoxylindole 
• 99275-48-6 1-t-butoxy-2-iodo-5-methoxyindole 
• 1428884-68-7 potassium (1-((tert-butoxy)carbonyl)-5-methoxy-1H-indol-2-yl)trifluoroboranuide 

Relevant articles and documents

An entry to 2-(cyclobut-1-en-1-yl)-1: H -indoles through a cyclobutenylation/deprotection cascade

A transition-metal-free strategy for the synthesis of 2-(cyclobut-1-en-1-yl)-1H-indoles under mild conditions is described herein. A series of substituted 2-(cyclobut-1-en-1-yl)-1H-indoles are accessed by a one-pot cyclobutenylation/deprotection cascade from N-Boc protected indoles. Preliminary experimental and density functional theory calculations suggest that a Boc-group transfer is involved in the underlying mechanism.

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.

Synthesis and antitumor activity of new thiazole nortopsentin analogs

New thiazole nortopsentin analogs in which one of the two indole units was replaced by a naphthyl and/or 7-azaindolyl portion, were conveniently synthesized. Among these, three derivatives showed good antiproliferative activity, in particular against MCF7 cell line, with GI50 values in the micromolar range. Their cytotoxic effect on MCF7 cells was further investigated in order to elucidate their mode of action. Results showed that the three compounds act as pro-apoptotic agents inducing a clear shift of viable cells towards early apoptosis, while not exerting necrotic effects. They also caused cell cycle perturbation with significant decrease in the percentage of cells in the G0/G1 and S phases, accompanied by a concomitant percentage increase of cells in the G2/M phase, and appearance of a subG1-cell population.