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

Downstream Products

• 159590-02-0 N-(tert-butyldimethylsilyl)indol-3-ylboronic acid 
• 452897-62-0 N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl]thiophen-2-ylmethyl]-4-methylbenzenesulfonamide 
• 452897-57-3 N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl]phenylmethyl]-4-methylbenzenesulfonamide 
• 452897-60-8 N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl]pyridin-2-ylmethyl]-4-methylbenzenesulfonamide 
• 452897-59-5 N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl]-(4-chlorophenyl)methyl]-4-methylbenzenesulfonamide 
• 452897-58-4 N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl](4-methoxyphenyl)methyl]-4-methylbenzenesulfonamide 
• 452897-61-9 N-[[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl](2-trifluoromethylphenyl)methyl]-4-methylbenzenesulfonamide 
• 452897-63-1 N-[Anthracen-9-yl-[1-(tert-butyldimethylsilanyl)-1H-indol-3-yl]methyl]-4-methylbenzenesulfonamide 
• 282550-29-2 2-(1-tert-butyldimethylsilylindol-3-yl)ethyl tosylate 
• 26988-87-4 L-homotryptophan 
• 83-34-1 3-Methylindole 
• 487-89-8 Indole-3-carboxaldehyde 
• 17771-42-5 3-(3-methyl-2-butenyl)indole 
• 15224-25-6 3-benzoylindole 

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.

Electron transfer-induced reduction of organic halides with amines

Reduction of a variety of organo halides was examined by using amines as a sacrificial hydrogen source. UV light-induced reduction of vinyl and aryl halides with triethylamine proceeded smoothly to give the corresponding reduced products. High temperature heating also caused the reduction and DABCO (1,4-diazabicyclo[2.2.2]octane) also served as a good reducing reagent.

Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents

The C–H indolation of heteroarenes was realized using the benziodoxolone hypervalent iodine reagents indoleBXs. Functionalization of the C–H bond in bipyridinones and quinoline N-oxides catalyzed by a rhodium complex allowed to incorporate indole rings into aza-heteroaromatic compounds. These new transformations displayed complete regioselectivity for the C-6 position of bipyridinones and the C-8 position of quinoline N-oxides and tolerated a broad range of functionalities, such as halogens, ethers, or trifluoromethyl groups.