18173-64-3

Basic information

• Product Name: TERT-BUTYLDIMETHYLSILANOL
• Synonyms: T-BUTYLDIMETHYLSILANOL;TERT-BUTYLDIMETHYLSILANOL;Butyldimethylsilanol;Silanol, (1,1-dimethylethyl)dimethyl-;SIB1939.0 !! T-BUTYLDIMETHYLSILANOL;tert-Butyldimethyl(hydroxy)silane;tert-Butyldimethylhydroxysilane;tert-ButyldiMethylsilanol 99%
• CAS NO: 18173-64-3
• Molecular Formula: C₆H₁₆OSi
• Molecular Weight: 132.28
• Product Categories: Organometallic Reagents;Organosilicon;Silanols
• Mol File: 18173-64-3.mol
• Article Data: 39

Chemical Properties

• Melting Point: 18 °C
• Boiling Point: 139 °C739 mm Hg(lit.)
• Flash Point: 113 °F
• Appearance: colorless transparent liquid
• Density: 0.84 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0165mmHg at 25°C
• Refractive Index: n20/D 1.424(lit.)
• PKA: 15.37±0.53(Predicted)
• BRN: 1732777
• CAS DataBase Reference: TERT-BUTYLDIMETHYLSILANOL(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYLDIMETHYLSILANOL(18173-64-3)
• EPA Substance Registry System: TERT-BUTYLDIMETHYLSILANOL(18173-64-3)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 18173-64-3(Hazardous Substances Data)

Usage

Description

TERT-BUTYLDIMETHYLSILANOL is a chemical compound that serves as a silylating agent for the protection of hydroxyl groups through silylation. It is known for its ability to facilitate various chemical reactions and synthesis processes in different industries.

Uses

Used in Pharmaceutical Industry:
TERT-BUTYLDIMETHYLSILANOL is used as a silylating agent for the protection of hydroxyl groups in the synthesis of pharmaceutical compounds. Its ability to protect hydroxyl groups allows for cleaner reactions and easier purification of the final product.
Used in Chemical Synthesis:
TERT-BUTYLDIMETHYLSILANOL is used as an initiator for the polymerization of 1,2 benzenedicarboxaldehyde. This application is crucial in the production of certain types of polymers and resins.
Used in Organic Chemistry:
TERT-BUTYLDIMETHYLSILANOL is used in the preparation of α-chiral ether derivatives by catalytic asymmetric allylic substitution. This process is essential in the synthesis of enantiomerically pure compounds, which are important in various fields such as pharmaceuticals and agrochemicals.
Used in Synthesis of Enol Silyl Ethers:
TERT-BUTYLDIMETHYLSILANOL is used in the synthesis of enol silyl ethers, which are key intermediates in various organic reactions. These enol silyl ethers can be used to protect enolizable ketones and aldehydes, allowing for selective reactions to occur at other sites on the molecule.

InChI:InChI=1/C6H6N2O2/c1-5-3-2-4-6(7-5)8(9)10/h2-4H,1H3

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 61012-65-5 C₁₅H₃₉NOSi₃ 
• 541-05-9 Hexamethylcyclotrisiloxane 
• 594-19-4 tert.-butyl lithium 
• 18052-27-2 tert-butyldimethyl(phenoxy)silane 
• 53172-91-1 (benzyloxy)(tert-butyl)dimethylsilane 
• 66031-93-4 tert-butyldimethylsilyl vinyl ether 
• 66324-10-5 tert-butyldimethyl(1-phenylvinyloxy)silane 
• 74812-76-3 O-(tert-butyldimethylsilyl)propen-2-ol 
• 74812-77-4 tert-Butyl-(1-cyclopropyl-vinyloxy)-dimethyl-silane 
• 114143-90-7 2-<(tert-butyldimethylsilyl)oxy>-4,6-dimethylpyrylium trifluoromethanesulfonate 
• 108794-10-1 4-[(tert-butyldimethylsilyl)oxy]-1-butene 
• 121444-55-1 2-(tert-Butyldimethylsilyl)-1,2-thiazetidine 1,1-dioxide 
• 141-78-6 ethyl acetate 

Downstream Products

• 82475-65-8 O-(tert-butyldimethylsilyl)-N-(2-chloroethyl)carbamate 
• 57711-50-9 3-[(1,1-dimethylethyl)dimethylsilyl]oxycholest-5-ene 
• 82475-66-9 O-(tert-butyldimethylsilyl)-N->phenylcarbamate 
• 146601-32-3 (4S,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-3,4-dimethyl-5-phenyl-[1,3,2]oxazaphospholidine 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Relevant articles and documents

Surface oxygen-assisted Pd nanoparticle catalysis for selective oxidation of silanes to silanols

Just add O2: Based on the fact that an oxygen-adsorbed Pd metal surface shows higher reactivity for water dissociation than a clean Pd surface, carbon-supported Pd nanoparticles (NPs) with surface oxygen atoms were developed as a highly effective and reusable heterogeneous catalyst for selective oxidation of silanes to silanols with water as a green oxidant (see figure). Copyright

Catalysis by cationic oxorhenium(v): Hydrolysis and alcoholysis of organic silanes

The cationic [2-(2′-hydroxyphenyl)-2-oxazolinato(-2)]oxorhenium(v) complex 1 promotes oxidative dehydrogenation of organosilanes with water and alcohols in a catalytic manner to give excellent yields of silanols and silyl ethers, respectively. The reactions proceed conveniently under ambient and open-flask conditions with low catalyst loading (≤1 mol%). The scope of the reaction with water is quite broad and includes aliphatic, aromatic, tertiary, secondary and primary silanes. The rate of reaction depends on the catalyst and silane concentrations and kinetic isotope effect measurements demonstrate involvement of the Si-H bond in the activated complex. The most influential factor on the silane affecting reactivity is steric hindrance and a quantitative correlation with the Taft steric parameter (E) is presented. A combination of kinetic data and isotope labelling results are used to discuss plausible mechanisms for the oxidative dehydrogenation reaction pathway.

Gold nanoparticles supported on the periodic mesoporous organosilica SBA-15 as an efficient and reusable catalyst for selective oxidation of silanes to silanols

Gold nanoparticles are confined and stabilized within the channels of SBA-15 through the poly(ionic liquid) brushes that are anchored onto the pore walls of SBA-15. The supported gold catalyst exhibited remarkably high catalytic activities for selective oxidation of silanes into silanols using water as an oxidant without the use of organic solvents.

Lewis acid-promoted reactions of γ-lactols with silyl enol ethers - Stereoselective formation of functionalized tetrahydrofuran derivatives

The monosubstituted γ-lactols 1a, 1b, 1c, and 1d and the disubstituted γ-lactol 1e were converted into tetrahydrofuran derivatives by reaction with typical silyl enol ethers in the presence of Lewis acids. Although the most suitable Lewis acid appears to be zinc chloride, BF3·Et2O or diethylaluminium chloride are also suitable under appropriate conditions. The stereoselectivities of these substitution reactions are similar to those observed with other silylated nucleophiles; however, there are several important differences. A comparison of the diastereoselectivities of different γ-lactols and of various silylated nucleophiles and organometallic compounds will also be presented in this paper.

Highly Selective Hydroxylation and Alkoxylation of Silanes: One-Pot Silane Oxidation and Reduction of Aldehydes/Ketones

An efficient chemoselective iridium-catalyzed method for the hydroxylation and alkoxylation of organosilanes to generate hydrogen gas and silanols or silyl ethers was developed. A variety of sterically hindered silanes with alkyl, aryl, and ether groups were tolerated. Furthermore, this atom-economical catalytic protocol can be used for the synthesis of silanediols and silanetriols. A one-pot silane oxidation and chemoselective reduction of aldehydes/ketones was also realized.

Hafnium Triflate as a Highly Potent Catalyst for Regio- and Chemoselective Deprotection of Silyl Ethers

As a Group IVB transition metal Lewis acid, hafnium triflate [Hf(OTf) 4 ] exhibited exceptionally high potency in desilylations. Since the amounts of Hf(OTf) 4 required for the deprotection of 1°, 2°, 3° alkyl and aryl tert -butyldimethylsilyl (TBS) ethers are significantly different, ranging from 0.05 mol% to 3 mol%, regioselective deprotection of TBS could be easily implemented. Moreover, chemoselective cleavage of different silyl ethers or removal of TBS in the presence of most hydroxyl protecting groups was also accomplished. NMR analyses of silyl products from TBS deprotection indicated that Hf(OTf) 4 -catalyzed desilylation may proceed via different mechanisms, depending on the solvent used.