784161-48-4

Basic information

• Product Name: 1-Boc-2-indolyldimethylsilanol, 95%
• Synonyms: 1-Boc-2-indolyldimethylsilanol, 95%;2-(hydroxydimethylsilyl)-1,1-dimethylethylindole-1-carboxylic acid ester;tert-butyl 2-[hydroxy(dimethyl)silyl]indole-1-carboxylate
• CAS NO: 784161-48-4
• Molecular Formula: C₁₅H₂₁NO₃Si
• Molecular Weight: 291.42
• Product Categories: Building Blocks;C13 to C27;Chemical Synthesis;Heterocyclic Building Blocks;Indoles
• Mol File: 784161-48-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 397.5°C at 760 mmHg
• Flash Point: >110°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 4.94E-07mmHg at 25°C
• Refractive Index: n20/D 1.545
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-Boc-2-indolyldimethylsilanol, 95%(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-2-indolyldimethylsilanol, 95%(784161-48-4)
• EPA Substance Registry System: 1-Boc-2-indolyldimethylsilanol, 95%(784161-48-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 784161-48-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 784161-48-4 differently. You can refer to the following data:
1. N-Boc-2-indolyldimethylsilanol is a useful silicon nucleophile for Pd-catalyzed cross-coupling.4
2. Reactant for:Palladium-catalyzed cross-coupling reactions

InChI:InChI=1/C15H21NO3Si/c1-15(2,3)19-14(17)16-12-9-7-6-8-11(12)10-13(16)20(4,5)18/h6-10,18H,1-5H3

Upstream product

• 75400-67-8 indole-1-carboxylic acid tert-butyl ester 
• 75-78-5 dimethylsilicon dichloride 

Downstream Products

• 1528-74-1 4,4'-dinitrobiphenyl 
• 193810-88-7 2-(4-nitrophenyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester 
• 605-39-0 2,2'-dimethyl-1,1'-biphenyl 
• 4877-93-4 2,2'-Dimethoxybiphenyl 
• 604-53-5 1,1'-bisnaphthalene 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 157427-60-6 2-(4-cyanophenyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester 
• 157427-61-7 2-[4-(ethoxycarbonyl)phenyl]-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester 
• 958-96-3 3,3'-dinitro-1,1'-biphenyl 
• 92-52-4 biphenyl 
• 138343-89-2 tert-butyl 2-phenyl-1H-indole-1-carboxylate 

Relevant articles and documents

Palladium-catalyzed cross-coupling of five-membered heterocyclic silanolates

(Chemical Equation Presented) The preparation of π-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.