22515-29-3

Basic information

• Product Name: methyl 3-(trimethylsilyl)benzoate
• Synonyms: methyl 3-(trimethylsilyl)benzoate
• CAS NO: 22515-29-3
• Molecular Weight: 208.332
• Mol File: 22515-29-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 3-(trimethylsilyl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-(trimethylsilyl)benzoate(22515-29-3)
• EPA Substance Registry System: methyl 3-(trimethylsilyl)benzoate(22515-29-3)

Safety Data

• Hazardous Substances Data: 22515-29-3(Hazardous Substances Data)

Upstream product

• 61518-42-1 methyl 3-trimethylsilylcyclohexa-1,4-dienecarboxylate 
• 61518-40-9 methyl 6-trimethylsilylcyclohexa-1,4-dienecarboxylate 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 618-91-7 methyl 3-iodo-benzoate 
• 15290-28-5 3-trimethylsilylbenzoic acid 
• 77-78-1 dimethyl sulfate 
• 17878-47-6 (3-bromophenyl)trimethylsilane 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 1379761-50-8 C₁₇H₁₈O₃ 
• 24251-07-8 methyl 3-(benzo[b]thiophene-3-yl)benzoate 
• 1023489-11-3 C₁₆H₁₂O₂S 

Relevant articles and documents

Gold-catalysed oxyarylation of styrenes and mono- and gem-disubstituted olefins facilitated by an iodine(III) oxidant

1-Hydroxy-1,2-benziodoxol-3(1H)-one (IBA) is an efficient terminal oxidant for gold-catalysed, three-component oxyarylation reactions. The use of this iodine(III) reagent expands the scope of oxyarylation to include styrenes and gem-disubstituted olefins, substrates that are incompatible with the previously reported Selectfluor-based methodology. Diverse arylsilane coupling partners can be employed, and in benzotrifluoride, homocoupling is substantially reduced. In addition, the IBA-derived co-products can be recovered and recycled. The I's have it: The unprecedented use of an iodine(III) reagent as the terminal oxidant for gold-catalysed oxyarylation allows the substrate scope to be significantly expanded; in addition to monosubstituted olefins, styrenes and gem-disubstituted olefins are well tolerated (see scheme). With benzotrifluoride as solvent, unproductive homodimerisation of the arylsilane coupling partner is effectively suppressed. Copyright

A flow microreactor system enables organolithium reactions without protecting alkoxycarbonyl groups

A flow microreactor system consisting of micromixers and microtube reactors provides an effective tool for the generation and reactions of aryllithiums bearing an alkoxycarbonyl group at para-, meta-, and ortho-positions. Alkyl p- and m-lithiobenzoates were generated by the I/Li exchange reaction with PhLi. The Br/Li exchange reactions with sBuLi were unsuccessful. Subsequent reactions of the resulting aryllithiums with electrophiles gave the desired products in good yields. On the other hand, alkyl o-lithiobenzoates were successfully generated by the Br/ Li exchange reaction with sBuLi. Subsequent reactions with electrophiles gave the desired products in good yields.