40899-73-8

Basic information

• Product Name: 1-[tert-butyl(dimethyl)silyl]-1H-indole
• Synonyms: 1H-Indole, 1-[(1,1-dimethylethyl)dimethylsilyl]-
• CAS NO: 40899-73-8
• Molecular Formula: C₁₄H₂₁NSi
• Molecular Weight: 231.4087
• Mol File: 40899-73-8.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 247.56°C at 760 mmHg
• Flash Point: 103.521°C
• Density: 0.918g/cm³
• Vapor Pressure: 0.025mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: 1-[tert-butyl(dimethyl)silyl]-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[tert-butyl(dimethyl)silyl]-1H-indole(40899-73-8)
• EPA Substance Registry System: 1-[tert-butyl(dimethyl)silyl]-1H-indole(40899-73-8)

Safety Data

• Hazardous Substances Data: 40899-73-8(Hazardous Substances Data)

Usage

Type of compound

Chemical compound

Derivative of

Indole (a heterocyclic aromatic organic compound)

Structure

Contains a tert-butyl group and a dimethylsilyl group attached to the nitrogen atom of the indole ring

Usage

Commonly used as a reagent in organic synthesis

Chemical behavior

Acts as a nucleophile in various chemical reactions

Investigation

Has been studied for its potential pharmacological properties, particularly in the field of medicinal chemistry

Upstream product

• 120-72-9 indole 
• 108613-05-4 t-butyldimethylsilyl trichloroacetate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 193694-04-1 N-TBS-4-bromoindole 
• 29681-57-0 tert-butyldimethylsilane 
• 16982-67-5 sodium salt of indole 
• 108940-04-1 1-(pivaloyloxymethyl)indole 
• 5031-11-8 1-hydroxymethyl-1H-indole 
• 153942-69-9 3-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-indole 
• 1003-09-4 2-bromothiophene 
• 159590-02-0 N-(tert-butyldimethylsilyl)indol-3-ylboronic acid 
• 108030-46-2 (E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene 
• 74-88-4 methyl iodide 

Downstream Products

• 861890-76-8 C₂₆H₃₆N₂O₂Si 
• 861890-77-9 C₂₆H₃₆N₂O₂Si 
• 861890-78-0 C₂₆H₃₆N₂O₂Si 
• 1046828-55-0 C₂₆H₃₅ClN₂O₂Si 
• 1046828-50-5 C₂₆H₃₅FN₂O₂Si 
• 1046828-51-6 C₂₆H₃₅FN₂O₂Si 
• 1046828-62-9 C₂₉H₄₂N₂O₂Si 
• 1046828-64-1 C₃₂H₄₀N₂O₂Si 
• 1046828-61-8 C₂₇H₃₈N₂O₃Si 
• 1046828-49-2 C₂₇H₃₈N₂O₂Si 
• 1046828-48-1 C₂₇H₃₈N₂O₂Si 
• 1046828-47-0 C₂₇H₃₈N₂O₂Si 
• 1046828-53-8 C₂₆H₃₅FN₂O₂Si 
• 1046828-58-3 C₂₆H₃₅BrN₂O₂Si 

Relevant articles and documents

Enantioselective Synthesis of Pyrrolizin-1-ones via Lewis Base Catalyzed N-Allylation of N-Silyl Pyrrole Latent Nucleophiles

Pyrrolizidine alkaloids and their derivatives often feature interesting biological activities. A class of substituted 2,3-dihydro-1H-pyrrolizin-1-one derivatives has been explored as a potential treatment for Alzheimer's disease, but enantioselective synthesis of these molecules is still elusive. We report that enantioselective N-allylation of N-silyl pyrrole latent nucleophiles with allylic fluorides followed by hydrogenation and diastereoselective Friedel-Crafts cyclization constitute an efficient synthetic route to access enantioenriched substituted 2,3-dihydro-1H-pyrrolizin-1-ones.

Iridium- and Rhodium-Catalyzed Directed C-H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents

The C-H heteroarylation of benzaldehydes with indoles and pyrroles was realized using the benziodoxolone hypervalent iodine reagents indole- and pyrroleBX. Functionalization of the aldehyde C-H bond using either an o-hydroxy or amino directing group and catalyzed by an iridium or a rhodium complex allowed the synthesis of salicyloylindoles and (2-sulfonamino)benzoylindoles, respectively, with good to excellent yields (74-98%). This new transformation could be carried out under mild conditions (rt to 40 °C) and tolerated a broad range of functionalities, such as ethers, halogens, carbonyls, or nitro groups.

Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor–Acceptor meso-Diaminocyclopropanes

The first Lewis acid catalyzed enantioselective ring-opening desymmetrization of a donor–acceptor meso-diaminocyclopropane is reported. The copper(II)-catalyzed Friedel–Crafts alkylation of indoles and one pyrrole with an unprecedented meso-diaminocyclopropane delivered enantioenriched, diastereomerically pure urea products, which are structurally related to natural and synthetic bioactive compounds. The development of a new ligand through the investigation of an underexplored subclass of bis(oxazoline) ligands was essential for achieving high enantioselectivities.