92669-93-7

Basic information

• Product Name: Silane, (2,6-dimethoxyphenyl)trimethyl-
• CAS NO: 92669-93-7
• Molecular Formula: C11H18O2Si
• Molecular Weight: 210.348
• Mol File: 92669-93-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Silane, (2,6-dimethoxyphenyl)trimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, (2,6-dimethoxyphenyl)trimethyl-(92669-93-7)
• EPA Substance Registry System: Silane, (2,6-dimethoxyphenyl)trimethyl-(92669-93-7)

Safety Data

• Hazardous Substances Data: 92669-93-7(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 151-10-0 1,3-Dimethoxybenzene 
• 634-36-6 1,2,3-trimethoxybenzene 

Downstream Products

• 1259290-72-6 C₁₂H₁₆O₅ 
• 1066-40-6 Trimethylsilanol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 151-10-0 1,3-Dimethoxybenzene 
• 2040-04-2 2,6-dimethoxyacetophenone 
• 16932-45-9 1-bromo-2,6-dimethoxybenzene 
• 16932-44-8 2-iodo-1,3-dimethoxybenzene 
• 16932-49-3 2,6-dimethoxybenzonitrile 
• 92669-94-8 1,3-bis(trimethylsilyl)-2,6-dimethoxybenzene 
• 1825-61-2 Trimethylmethoxysilane 

Relevant articles and documents

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Functionalisation in 2 position of benzenes 1,3-disubstituted by para-directing groups has been investigated, involving 2-trimethylsilylated intermediates when the classical methods (particularly these involving the anion in 2 position) are ineffective. Thus 2-trimethylsilyl derivatives of 1,3-dihalo- or 1,3-dimethoxybenzene have been prepared in good yields. Their conversion into the corresponding 1,2,3-trisubstituted benzenes has been conveniently performed upon acetylation, iodination or sulfonation, except in the case of the sulfonation of the 1,3-dimethoxylated compound in which the ipso effect of the silyl group is surpassed by the directing effect of the methoxy substituents. In contrast, whith the same substrate, cyanation in position 2 was successfully carried out using chlorosulfonyl isocyanate: to our knowledge this reaction is the first example of substitution of a trimethylsilyl by a cyano group in the aromatic series.

Method for orthometalation of a carbocyclic aromatic derivative bearing at least an electron donor group

The invention concerns a method for orthometalation of a carbocyclic aromatic derivative bearing at least an electron donor group, characterised in that it consists in reacting said carbocyclic aromatic derivative with an efficient amount of at least one alkaline metal in the presence of a compound of formula (I): RX, wherein: R represents a hydrocarbon radical having 1 to 20 carbon atoms which can be a saturated or unsaturated, linear or branched, acyclic aliphatic radical; a saturated or unsaturated, monocyclic or polycyclic cycloaliphatic radical; a saturated or unsaturated, linear or branched aliphatic radical bearing a cyclic substituent; and X represents a bromine or chlorine atom.

Regioselective Reductive Electrophilic Substitution of 1,2,3-Trimethoxybenzene and Its 5-Alkyl-Substituted Homologues

The methoxy group in the 2-position of 1,2,3-trimethoxybenzene (1) can be regioselectively removed by electron transfer from alkali metals and replaced with a variety of electrophiles in a one-pot procedure, affording 2-substituted resorcinol dimethyl ethers.The usefulness of this synthetic method is illustrated by numerous examples.This reaction procedure has been successfully extended to the 5-methyl-substituted homologue (2), but limitations occur with the higher homologue 1-pentyl-3,4,5-trimethoxybenzene (3).Investigations on the mechanism of demethoxylation, with the aid of labeling experiments, provided clear evidence for the intermediacy of aryl radicals and explained the low yields obtained in the reductive electrophilic substitution of compound 3.