101803-60-5

Basic information

• Product Name: Silane, (1,1-dimethylethyl)[(4-methoxyphenyl)methoxy]dimethyl-
• CAS NO: 101803-60-5
• Molecular Formula: C14H24O2Si
• Molecular Weight: 252.429
• Mol File: 101803-60-5.mol

Chemical Properties

• CAS DataBase Reference: Silane, (1,1-dimethylethyl)[(4-methoxyphenyl)methoxy]dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, (1,1-dimethylethyl)[(4-methoxyphenyl)methoxy]dimethyl-(101803-60-5)
• EPA Substance Registry System: Silane, (1,1-dimethylethyl)[(4-methoxyphenyl)methoxy]dimethyl-(101803-60-5)

Safety Data

• Hazardous Substances Data: 101803-60-5(Hazardous Substances Data)

Upstream product

• 29681-57-0 tert-butyldimethylsilane 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 
• 54925-64-3 N-(tert-butyldimethylsilyl)imidazole 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 19927-28-7 p-methoxybenzyl thiocyanate 
• 70887-29-5 4-methoxybenzyl iodide 
• 24318-41-0 p-methoxybenzyl benzoate 
• 1431564-03-2 (2S,3S)-methyl 5-methoxy-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate 
• 1431563-78-8 C₂₄H₃₄O₅Si 
• 1431563-84-6 (2S,3S)-methyl 3-((tert-butyldimethylsilyl)oxy)-2-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)propanoate 
• 1431564-25-8 (2S,3S)-5,6-dimethoxy-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid 
• 1431564-09-8 (2S,3S)-methyl 5,6-dimethoxy-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate 
• 1431563-99-3 (2S,3S)-methyl 2-(3,4-dimethoxyphenyl)-3-hydroxy-3-(4-methoxyphenyl)propanoate 
• 1431563-92-6 (2S,3S)-methyl 3-hydroxy-2-(3-methoxyphenyl)-3-(4-methoxyphenyl)propanoate 
• 98446-83-4 1-methoxy-4-[(propan-2-yloxy)methyl]benzene 
• 55249-73-5 1-ethoxymethyl-4-methoxybenzene 
• 1515-81-7 1-methoxy-4-(methoxymethyl)benzene 
• 123-11-5 4-methoxy-benzaldehyde 

Relevant articles and documents

Highly sulphated cellulose: a versatile, reusable and selective desilylating agent for deprotection of alcoholic TBDMS ethers

A mild, efficient and rapid protocol was developed for the deprotection of alcoholic TBDMS ethers using a recyclable, eco-friendly highly sulphated cellulose sulphate acid catalyst in methanol. This acid catalyst selectively cleaves alcoholic TBDMS ethers in bis-TBDMS ethers containing both alcoholic and phenolic TBDMS ether moieties.

Oxidative Cleavage of Silyl Ethers by an Oxoammonium Salt

A method for the oxidative cleavage of silyl ethers to their corresponding carbonyl species mediated by an oxoammonium salt is described. The resulting aldehydes and ketones are obtained under mild reaction conditions with no observed overoxidation. For robust substrates, heating to reflux temperatures significantly reduces the reaction time.

Preparation of nano silica supported sodium hydrogen sulfate: As an efficient catalyst for the trimethyl, triethyl and t-butyldimethyl silylations of aliphatic and aromatic alcohols in solution and under solvent-free conditions

Nano silica supported sodium hydrogen sulfate has been prepared by mixing NaHSO4 with activated Nano silicagel. We wish to report a new method for the synthesis of trimethyl (TMS), triethyl (TES) and t-butyldimethyl silyl (TBS) ethers from benzylic, allylic, propargylic alcohols, phenols, naphtholes and some of phenolic drugs in the solution and under solvent-free conditions.

Sequential C-H functionalization reactions for the enantioselective synthesis of highly functionalized 2,3-dihydrobenzofurans

The enantioselective synthesis of 2,3-dihydrobenzofurans was achieved by using two sequential C-H functionalization reactions, a rhodium-catalyzed enantioselective intermolecular C-H insertion followed by a palladium-catalyzed C-H activation/C-O cyclization. Further diversification of the 2,3-dihydrobenzofuran structures was possible by a subsequent palladium-catalyzed intermolecular Heck-type sp2 C-H functionalization.

Potassium tert-butoxide-catalyzed dehydrogenative Si-O coupling: Reactivity pattern and mechanism of an underappreciated alcohol protection

A remarkable fen-butoxide-catalyzed coupling of alcohols and silanes is reported. Dihydrogen and not hydrochloric acid (generated in the prevalent, related coupling of alcohols and chlorosilanes) is formed as the sole by-product. A comprehensive survey of common silanes provides a reliable tool for the predictability of their reactivity under defined reaction conditions. The debated mechanism of this transformation is investigated monitoring the stereochemical course at the silicon atom by means of a silicon-stereogenic silane. On this basis, a transition state for the enantiospecific Si-O coupling step is suggested rationalizing the observed frontside attack and thus retention at the silicon atom.

The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide

An efficient and chemoselective cleavage of silyl ethers (primary, secondary and aromatic) by using catalytic quantities of trimethylsilyl bromide (TMSBr) in methanol is reported. A wide range of alkyl silyl ethers such as TBS, TIPS, and TBDPS can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The deprotection of silyl esters was also achieved employing catalytic quantities of TMSBr. The Royal Society of Chemistry 2008.

Selective oxidation of benzylic alcohols and TBDMS ethers to carbonyl compounds with CrO3-H5IO6

Benzyl alcohols and benzyl TBDMS ethers were efficiently oxidized to the corresponding carbonyl compounds in high yield with periodic acid catalyzed by CrO3 at low temperature (-78°C). The oxidation procedure was highly functional group tolerant and very selective for the TBDMS group over the TBDPS group. Georg Thieme Verlag Stuttgart.

Reversing the role of the metal - oxygen π-bond. Chemoselective catalytic reductions with a rhenium(V)-dioxo complex

The metal-oxygen bond plays a critical role in some of the most important biological and synthetic reactions. However, the majority of these processes result in the oxidation of the target organic substrate; applications of this class of metal complexes to other organic transformations are extremely rare. In this paper, we report a new type of catalytic process in which complexes with metal-oxygen multiple bonds are used as reductants rather than oxidants. The overall reaction provides a highly chemoselective reduction/protection of carbonyl groups. In addition to providing a new way of catalyzing organic reactions, these catalysts can be used in the presence of a wide range of other functional groups such as amino, cyano, nitro, aryl halo, ester, and alkene; unlike many of their late metal relatives, they are inexpensive as well as air and moisture tolerant. Copyright

A Convenient Method for Protection and Deprotection of Alcohols and Phenols as Alkylsilyl Ethers Catalyzed by Iodine under Microwave Irradiation

Irradiation of alcohols or phenols with tert-butyldimethylsilyl chloride (TBDMSCl) or trimethylsilyl chloride (TMSCl) in presence of catalytic amount (20 mol%) of iodine in a microwave oven for 2 min gives the corresponding silyl ethers in excellent yield. Iodine in methanol deprotects the silyl ether into its parent alcohol or phenol under similar reaction conditions.

Effective silylation of carboxylic acids under solvent-free conditions with tert-butyldimethylsilyl chloride (TBDMSCL) and triisopropylsilyl chloride (TIPSCL)

Varions types of carboxylic acids can be converted effectively to their corresponding TBDMS and TIPS esters using TBDMSCI and TIPSCI in the presence of imidazole under solvent-free conditions. The advantage of this modified method in comparison with that reported by Corey is the elimination of DMF, which eliminates aqueous work-up. The method is not a time-consuming process and the reactions proceed spontaneously. By this method, absolute chemoselectivity for the protection of carboxylic acid functions in the presence of 2°, 3° hydroxyl groups are observed.