139140-16-2

Basic information

• Product Name: Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-methoxy-
• CAS NO: 139140-16-2
• Molecular Formula: C14H24O3Si
• Molecular Weight: 268.428
• Mol File: 139140-16-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-methoxy-(139140-16-2)
• EPA Substance Registry System: Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-methoxy-(139140-16-2)

Safety Data

• Hazardous Substances Data: 139140-16-2(Hazardous Substances Data)

Upstream product

• 139140-12-8 tert-butyl(4-(tert-butyldimethylsilyloxy)-3-methoxybenzyloxy)dimethylsilane 
• 498-00-0 4-hydroxymethyl-2-methoxyphenol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 596845-69-1 (4-allyloxy-3-methoxy-benzyloxy)-tert-butyl-dimethyl-silane 

Downstream Products

• 174840-51-8 4-(hydroxymethyl)-2-methoxyphenyl benzoate 

Relevant articles and documents

An efficient and chemoselective deprotection of tert-butyldimethylsilyl (TBDMS) ethers using tailor-made ionic liquid

Phenolic tert-butyldimethylsilyl (TBDMS) ethers can be deprotected to yield phenols in excellent yield using tailor-made ionic liquid [dihexaEGim][OMs] (dihexaEGim = dihexaethylene glycolic imidazolium salt) as an organic catalyst with alkali-metal fluoride in tert-amyl alcohol. On the contrary, all TBDMS protecting groups can be cleaved cleanly from the bis-TBDMS ether using the same reaction in CH3CN solvent instead of tert-alcohol at 100 °C. This [dihexaEGim][OMs]/tert-amyl alcohol media system allows the highly selective phenolic deprotection reaction of various bis-TBDMS ethers containing both phenolic and aliphatic TBDMS ethers to provide the corresponding phenols in high yield.

Selective O-deallylation of o-allyloxyanisoles

o-Allyloxyanisoles are selectively and easily deallylated by treatment with sec- or tert-butyllithium at low temperature. The reaction is proposed to proceed through a tandem intermolecular carbolithiation-β;-elimination process, which can also be considered an SN2′ attack of the organolithium on the allyl ether.

Selective desilylation of tert-butyldimethylsilyl ethers of phenols using potassium fluoride-alumina and ultrasound

The use of potassium fluoride on basic alumina in acetonitrile with ultrasound for the selecting deprotection of tert-butyldimethylsilyl ethers of phenols is described. The method, which features a non-aqueous work-up, readily cleaves tert-butyldimethylsilyl ethers of phenols at room temperature, whereas tert-butyldimethylsilyl ethers of benzyl alcohols or 2-(trimethylsilyl) ethoxymethyl ethers of phenols are stable.