27798-53-4

Usage

Usage

Organic synthesis, medicinal chemistry

Composition

Derivative of benzoic acid with a methoxy group and a trimethylsilyloxy group attached to the benzene ring

Applications

Preparation of pharmaceuticals, agrochemicals, and other biologically active molecules; building block for the synthesis of complex organic compounds

Functional Group

Methoxy group (-OCH3), trimethylsilyloxy group (-OSi(CH3)3)

Protective Function

Trimethylsilyloxy group can protect the carboxylic acid functionality, enabling selective transformations in organic chemistry.

Upstream product

• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 67-56-1 methanol 
• 1000180-41-5 2-(4-hydroxy-3-methoxyphenyl)-2-methoxyacetonitrile 
• 24589-78-4 N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide 
• 10416-58-7 N,N-bis(trimethylsilyl)acetamide 

Relevant academic research and scientific papers

Chemical defense of the crust fungus Aleurodiscus amorphus by a tailor-made cyanogenic cyanohydrin ether

(Chemical Equation Presented) A mighty midget! When injured, the crust fungus A. amorphus (left in the picture) releases hydrocyanic acid by an oxidative mechanism so far unknown in nature. In contrast to cyanogenic glycosides in which the smooth hydrolysis of the glycoside bond is essential for the liberation of hydrocyanic acid, in aleurodisconitrile the oxidation-prone aromatic moiety enables the release of hydrocyanic acid.

Metabolic pathways of 4-[(3-methoxyphenyl)methyl]-2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disila cyclohexane (MPSC) hydrochloride, a silicon-containing xenobiotic, in rat, dog, and man

The metabolic pathways of Sandoz compound 58-112, 4-[(3-methoxyphenyl)methyl]-2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disila cyclohexane (MPSC) hydrochloride were evaluated in rat, dog, and man after a single oral dose. In rat, dog and man the major route of elimination was renal. In the dog, renal excretion of unchanged MPSC represented a substantial portion of the dose whereas in rat and man MPSC was completely metabolized prior to excretion. In rat and man, the major end-product metabolite was 3'-[{(hydroxydimethylsilyl)methylamino}methyl]-phenol glucuronide; 4-[(3-hydroxyphenyl)-methyl]-2,2,6,6-tetramethyl-1-oxa-4-aza-2,6-disil acyclohexane and 4-[(4-hydroxy-3-methoxyphenyl)methyl]-2,2,6,6-tetramethyl-1-oxa-4-aza- 2,6-disilacyclohexane and their conjugates were also present. In dog, the major end-product metabolites were the hippurate of 3-methoxybenzoic acid and 3-hydroxybenzoic acid.

29Si and 13C NMR Spectra of 4-Substituted 2-Methoxytrimethylsiloxybenzenes. Factors Determining the Chemical Shifts in Models of Lignin Constituents

29Si and 13C NMR chemical shifts are reported for a series of twenty 4-substituted 2-methoxytrimethylsiloxybenzenes; the set of substituents incorporates a basic set of ten substituents differing in their relative polar and resonance effects and ten other

Fragmentation of Trimethylsilyl Derivatives of 2-Alkoxyphenols: a Further Violation of the 'Even-electron Rule'

The mass spectra of trimethylsilyl (TMS) ethers of 2-methoxyphenols show abundant +* ions originating from consecutive loss of two methyl radicals.This is illustrated by comparison of the accurate mass-measured and linked-scan spectra of the TMS derivatives of 2-methoxyphenol (guaiacol), 4-hydroxy-3-methoxybenzaldehyde (vanillin) and 3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid methyl ester (ferulic acid methyl ester) with those of the TMS derivatives of phenol, 4-hydroxybenzaldehyde, 3-(4-hydroxyphenyl)-2-propenoic acid methyl ester (p-coumaric acid methyl ester), 3-methoxyphenol and 4-methoxyphenol.This distinctive ortho effect is valuable in the identification of isomeric phenolic compounds.In the spectra of the TMS derivatives of 2-ethoxyphenol and 2-propoxyphenol the sequential loss of two radicals is less pronounced, because elimination of the side-chain and methyl group with rearrengement and hydrogen migration is competitive.