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

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 
• 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 
• 108030-46-2 (E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene 

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.

Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N-Allylations of N-Heterocycles

Latent nucleophiles are compounds that are themselves not nucleophilic but can produce a strong nucleophile when activated. Such nucleophiles can expand the scope of Lewis base catalyzed reactions. As a proof of concept, we report that N-silyl pyrroles, i

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.

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.

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.

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.

Indole- and Pyrrole-BX: Bench-Stable Hypervalent Iodine Reagents for Heterocycle Umpolung

The one-step synthesis of the bench-stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 °C and were applied in the C?H arylation of unactivated arenes using either rhodium or ruthenium catalysts. A broad range of heterocyclic systems of high interest for synthetic and medicinal chemistry was accessed in high yields. The developed C?H functionalization could not be achieved using reported reagents or methods, highlighting the unique reactivity of Indole- and Pyrrole-BX.

On water phosphine-free palladium-catalyzed room temperature C-H arylation of indoles

Get on top of your chemistry! An "on water", palladium-catalyzed, phosphine-free direct C-H arylation of indoles, with iodoarenes at 25-30°C, is disclosed (see scheme; TBDMS=N-tert-butyldimethylsilyl ether; SEM=N-2-(trimethylsilyl)ethoxymethyl; Bn=benzyl, Piv=pivabyl). The mildness of the reaction conditions permits the tolerance of a variety of N1-protected indoles.

3-Indolylphosphines as ligand for palladium in Suzuki-Miyaura coupling reaction of chloroarenes: Substituent effects

The ligand 1,3-bis(diphenylphosphino)-1H-indole, L1 with palladium promotes Suzuki-Miyaura coupling reaction of chloroarenes and benzyl chlorides with arylboronic acids. Structural modification of L1 established that the phosphine group at C-3 position of indole was crucial to catalysis and its efficacy depended on the nature of the N-substituent. 31P chemical shift values of the substituted indolylphosphines appear to show a correlation with observed trend in catalytic efficiency.

Asymmetric synthesis of indole homo-Michael adducts via dynamic kinetic Friedel-Crafts alkylation with cyclopropanes

An enantioconvergent Friedel-Crafts alkylation of indoles with donor-acceptor cyclopropanes is described. The reaction is catalyzed by pybox?MgI2 and proceeds via a type I dynamic kinetic asymmetric transformation (DyKAT).