475102-18-2

Basic information

• Product Name: 1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE
• Synonyms: 1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE
• CAS NO: 475102-18-2
• Molecular Formula: C₁₆H₂₃NO₃Si
• Molecular Weight: 305.44
• Mol File: 475102-18-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE(475102-18-2)
• EPA Substance Registry System: 1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE(475102-18-2)

Safety Data

• Hazardous Substances Data: 475102-18-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE is used as a precursor for the synthesis of various pharmaceuticals and agrochemicals due to its unique chemical structure and the presence of a BOC protecting group.
Used in Medicinal Chemistry:
1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE is used as a building block in drug discovery and development, enabling the creation of new compounds with potential therapeutic applications.
Used in Organic Synthesis:
1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE is used as a versatile intermediate in organic synthesis, allowing for the development of a wide range of chemical compounds.
Used in Anticancer Research:
1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE is used as a compound with potential anticancer properties, being studied for its ability to target and inhibit the growth of cancer cells.
Used in Antibacterial Applications:
1-BOC-2-(HYDROXY-DIMETHYL-SILANYL)-5-METHYL-INDOLE is used as a compound with potential antibacterial properties, being investigated for its ability to combat bacterial infections.

Upstream product

• 614-96-0 5-methyl-1H-indole 
• 129822-49-7 5-methylindole-1-carboxylic acid tert-butyl ester 
• 75-78-5 dimethylsilicon dichloride 
• 24424-99-5 di-tert-butyl dicarbonate 

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.

A non-cryogenic method for the preparation of 2-(indolyl) borates, silanes, and silanols

2-Indolyl borates are prepared via addition of LDA to a mixture of N-Bo-indole and triisopropyl borate at 0-5 °C. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).