10586-12-6

Usage

Type of compound

Silane compound

Structure

Contains three trimethylsilyloxy groups attached to a central benzene ring

Common use

Protecting group for hydroxyl groups in organic synthesis

Additional use

Building block in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals

Physical state

Colorless liquid

Odor

Slightly sweet

Flammability

Flammable

Safety precautions

Should be handled with care

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 108-73-6 3,5-dihydroxyphenol 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 1663-67-8 malonoyl dichloride 

Downstream Products

• 100334-99-4 2,4-Dichloro-benzoic acid 4-(2,4-dichloro-benzoyl)-3,5-dihydroxy-phenyl ester 
• 3875-68-1 1,3-dihydroxyxanthone 
• 61101-89-1 1,3-dihydroxy-6-chloro-9H-xanthone 
• 100334-95-0 7-chloro-1,3-dihydroxy-9H-xanthen-9-one 
• 108-73-6 3,5-dihydroxyphenol 
• 100334-98-3 2-Chloro-benzoic acid 4-(2-chloro-benzoyl)-3,5-dihydroxy-phenyl ester 

Relevant academic research and scientific papers

Preparation, characterization and use of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as an eco-benign, efficient and reusable ionic liquid catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups

New and novel ionic liquid (3-methyl-1-sulfonic acid imidazolium hydrogen sulfate) is a recyclable and eco-benign catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups under solvent-free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-8 min). The catalyst was characterized by FT-IR, 1H NMR and 13C NMR studies. All the products were extensively characterized by 1H NMR, IR, GC-MS and melting point analyses. A mechanism for the catalytic activity is proposed. The catalyst can be recovered and reused without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.

Succinimide-N-sulfonic acid: A mild, efficient, and reusable catalyst for the chemoselective trimethylsilylation of alcohols and phenols

Succinimide-N-sulfonic acid (SuSA) is easily prepared by the reaction of succinimide with chlorosulfonic acid. This reagent is able to efficiently catalyze the chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS). All reactions were performed under mild reaction conditions, giving excellent yields. Copyright Taylor & Francis Group, LLC.

Poly(4-vinylpyridine) catalyzed chemoselective O-TMS protection of alcohols and phenols and N-Boc protection of amines

Poly(4-vinylpyridine) (PVP) acts as an efficient and reusable catalyst for the selective and efficient trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) and N-tert-butoxycarbonylation of amines with (Boc)2O. All reactions were performed under mild conditions in good to high yields. Iranian Chemical Society 2012.

Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes

Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR, 1H NMR, 13C NMR and MS studies. All the products were extensively characterized by IR, 1H NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.

Nanocrystalline TiO2-HClO4 as a new, efficient and recyclable catalyst for the chemoselective trimethylsilylation of alcohols, phenols and deprotection of silyl ethers

TiO2-HClO4, as a new solid acid, was found to be an efficient catalyst for the chemoselective trimethylsilylation of alcohols and phenols. Deprotection of the resulting trimethylsilylethers was achieved using the same catalyst in methanol solvent. The synthesized catalyst was characterized by FT-IR, SEM, TEM, BET and XRD analyses. Our novel synthetic method has the advantages of high yields, short reaction times, low cost and recyclability of the catalyst, simplicity and easy work-up compared to the conventional methods reported in the literature.

Partition coefficients of ketones, phenols, aliphatic and aromatic acids, and esters in n-hexane/nitromethane

Liquid-liquid partition is used in sample preparation and in countercurrent and liquid-liquid chromatographic separations. Partition coefficients are widely used in toxicology, environmental, and analytical chemistry. The K hn determination procedure for the n-hexane/ nitromethane system was optimized and partition coefficients for 99 ketones, esters and trimethylsilyl derivatives of phenols, aliphatic and aromatic acids were determined. For 130 compounds, Khn values were predicted using mathematical relationships between Khn and other physicochemical and structural parameters. Versita Sp. z o.o.

Heteroadamantyl cannabinoids

The aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have synthesized a series of analogues in which the C3 position is substituted either directly or through a one-carbon atom link

Multicyclic poly(ether sulfone)s of phloroglucinol forming branched and cross-linked architectures

K2CO3-promoted polycondensations of phloroglucinol and 4,4′-difluorodiphenyl sulfone (DFDPS) in DMSO yielded mixtures of linear oligomers due to numerous side reactions. In contrast, polycondensations of silylated phloroglucinol under similar conditions were not plagued by such side reactions but involved various cyclization reactions with high efficiency. The MALDI-TOF mass spectra revealed the formation of various cyclic, bicyclic, and multicyclic species of complex structure up to 12000 Da. Therefore, cross-linking only occurred when a large excess (+30 mol %) of DFDPS was added. The resulting branched and cross-linked polymers mainly consisted of cyclic building blocks. Attempts to introduce sulfonic acid groups by alkylation of pendant OH groups with sultones gave only a moderate degree of substitution, due to the high degree of cyclization. For comparison two polycondensations of silylated 5-methylresorcinol were studied.

Enol Ethers, XVII. Acylation of Trimethylsilyl Enol Ethers with Malonyl Dichloride - Synthesis of 4-Hydroxy-2H-pyran-2-ones

Trimethylsilyl enol ethers of aldehydes 1, acyclic and cyclic ketones 4 and 10, respectively, are acylated by malonyl dichloride (2) at room temperature or even at -60 deg C.After aqueous workup, the 6-unsubstituted 4-hydroxy-2H-pyran-2-ones 3 are obtained from 1-(trimethylsiloxy)alkenes 1, whereas the 5,6-alkylene-bridged 4-hydroxy-2H-pyran-2-ones 11 are formed from 1-(trimethylsiloxy)cycloalkenes 10.Acylation of 2-(trimethylsiloxy)-1-propene (4a) and 3-(trimethylsiloxy)-2-pentene (4b) results in mixtures of 4-(trimethylsiloxy)-2H-pyran-2-ones 5 (main products) and phloroglucinol tris(trimethylsilyl) ethers (6) (by-products).

Cyclic Ions in the Mass Spectra of Trimethylsilyl Derivatives of Substituted o-Dihydroxybenzenes

The mass spectra of trimethylsilyl (TMS) ethers/methyl esters of phenolic acids containing o-dihydroxybenzene groups have base peaks at (1+) instead of the usual (1+) and (1+) that are characteristic of TMS/methyl esters of monohydroxyphenolic acids.These ions, formed by the loss of 31+88 u from the parent ion, possess a cyclic moiety as proven by substitution of deuterium atoms for hydrogen atoms in the TMS groups of the methyl esters of 3,4,5-trihydroxybenzoic (gallic), 3,4-dihydroxybenzoic (protocatechuic) and β-(3,4-dihydroxyphenyl)propenoic (caffeic) acids.Although these cyclic ions are the base peaks in TMS-derivatized o-dihydroxyphenolic acid esters, similar ions represent intense peaks but not neccessarily the base peak in other derivatized compounds such as 1,2-dihydroxybenzene, 1,2-dihydroxy-3-methyl- and 1,2-dihydroxy-4-methyl-benzenes and flavan-3-ols that possess o-dihydroxybenzene groups.Compounds possessing m- or p-dihydroxybenzene groups do not form these cyclic ions; therefore, this procedure for derivatization and interpretation of mass spectra is valuable for the identification of compounds containing o-dihydroxybenzene groups in complex mixtures of isomeric compounds.