85630-29-1

Basic information

• Product Name: 4-methoxy-2-trimethylsilylphenol
• Synonyms: 4-methoxy-2-trimethylsilylphenol
• CAS NO: 85630-29-1
• Molecular Weight: 196.321
• Mol File: 85630-29-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-methoxy-2-trimethylsilylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-2-trimethylsilylphenol(85630-29-1)
• EPA Substance Registry System: 4-methoxy-2-trimethylsilylphenol(85630-29-1)

Safety Data

• Hazardous Substances Data: 85630-29-1(Hazardous Substances Data)

Upstream product

• 17332-11-5 2-bromo-4-methoxyphenol 
• 4039-32-1 lithium hexamethyldisilazane 
• 150-76-5 4-methoxy-phenol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 75-05-8 acetonitrile 
• 556812-41-0 4-methoxy-2-(trimethylsilyl)phenyl triflate 
• 71-43-2 benzene 
• 762-72-1 allyl-trimethyl-silane 
• 1366440-94-9 4-methoxy-2-trimethylsilylphenyl diethylphosphate 
• 1366440-80-3 4-methoxy-2-trimethylsilylphenyl methanesulfonate 
• 75-89-8 2,2,2-trifluoroethanol 
• 75-77-4 chloro-trimethyl-silane 
• 1004322-70-6 2-chloro-5-methoxyphenyltrimethylsilane 

Downstream Products

• 944583-29-3 2-trimethylsilyl-4-methoxyacetanilide 
• 17876-90-3 3-trimethylsilylanisol 
• 1004322-78-4 2-(2,2,2-trifluoroethoxy)-5-methoxytrimethylsilylbenzene 
• 556812-41-0 4-methoxy-2-(trimethylsilyl)phenyl triflate 
• 1366440-94-9 4-methoxy-2-trimethylsilylphenyl diethylphosphate 
• 1366440-80-3 4-methoxy-2-trimethylsilylphenyl methanesulfonate 
• 95046-15-4 1-(hexa-1,2-dien-1-yl)-4-methoxybenzene 
• 72054-88-7 4,4-Dimethoxy-2-trimethylsilanyl-cyclohexa-2,5-dienone 

Relevant articles and documents

Trifluoromethyl aryl sulfonates (TFMS): An applicable trifluoromethoxylation reagent

Fluorine is probably another favorite hetero-atom for incorporation into small molecules after nitrogen. Among many fluorine-containing groups, trifluoromethyl aryl ethers (ArOCF3) have unique properties in drug design and are difficult to be synthesized, and many different methods were developed to prepare them. A novel one-pot synthesis of o-iodine-aryl trifluoromethyl ethers (ArOCF3I) was described by the reaction of trifluoromethoxylation and iodination with trifluoromethyl aryl sulfonates (TFMS) in this manuscript. The reaction conditions were optimized by screening different solvents, crown ethers, substrates and the ratios and the yields of products were in moderate to high yields (up to 86%).

Probing for a leaving group effect on the generation and reactivity of phenyl cations

Phenyl cations are smoothly generated by the photoheterolytic cleavage of an Ar-LG bond (LG = leaving group). With the aim of evaluating the scope of the method, a series of 4-methoxy-2-(trimethylsilyl)phenyl derivatives (sulfonic, LG = MeSO3 and CF3SO3, phosphate, LG = (EtO) 2(O)PO esters and the corresponding chloride) have been compared as probes for evaluating the leaving group ability. The photocleavage was a general reaction, with the somewhat surprising order (EtO)2(O)PO ～ Cl > CF3SO3 > MeSO3 (φ = 0.50 to 0.16 in CF3CH2OH and lower values in MeCN-H2O). The ensuing reactions did not depend on the LGs but only on the structure of the phenyl cation (the silyl group tuned the triplet to singlet intersystem crossing and the electrophilicity) and on the medium (formation of a complex with water slowed the electrophilic reactions).

A domino process for benzyne preparation: Dual activation of o-(trimethylsilyl)phenols by nonafluorobutanesulfonyl fluoride

Benzynes were generated from o-(trimethylsilyl)phenols using nonafluorobutanesulfonyl fluoride (NfF) by a domino process, i.e., the nonaflation of the phenolic hydroxyl group of o-(trimethylsilyl)phenols by NfF followed by the attack of the produced fluoride ion on the trimethylsilyl group. The generated benzyne immediately underwent various reactions to give polysubstituted benzenes.