77256-45-2

Basic information

• Product Name: allyl 2,4,6-triisopropylbenzoate
• Synonyms: allyl 2,4,6-triisopropylbenzoate
• CAS NO: 77256-45-2
• Molecular Weight: 288.43
• Mol File: 77256-45-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: allyl 2,4,6-triisopropylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 2,4,6-triisopropylbenzoate(77256-45-2)
• EPA Substance Registry System: allyl 2,4,6-triisopropylbenzoate(77256-45-2)

Safety Data

• Hazardous Substances Data: 77256-45-2(Hazardous Substances Data)

Upstream product

• 4333-56-6 cyclopropyl bromide 
• 49623-71-4 2,4,6-triisopropylbenzoic acid 
• 21524-34-5 2,4,6-triisopropyl-1-bromobenzene 
• 106-95-6 allyl bromide 

Downstream Products

• 77256-75-8 (Z)-2-Hydroxy-1-(2,4,6-triisopropyl-phenyl)-but-2-en-1-one 

Relevant articles and documents

Studies on the Lithiation, Borylation, and 1,2-Metalate Rearrangement of O-Cycloalkyl 2,4,6-Triisopropylbenzoates

A broad range of acyclic primary and secondary 2,4,6-triisopropylbenzoate (TIB) esters have been used in lithiation-borylation reactions, but cyclic TIB esters have not. We have studied the use of cyclic TIB esters in lithiation-borylation reactions and looked at the effect of ring size (3- → 6-membered rings) on the three key steps of the lithiation-borylation protocol: deprotonation, borylation and 1,2-metalate rearrangement. Although all rings sizes could be deprotonated, the cyclohexyl case was impractically slow, and the cyclopentyl example underwent α-elimination faster than deprotonation at ?78 °C and so could not be used. Both cyclobutyl and cyclopropyl cases underwent rapid borylation, but only the cyclobutyl substrate underwent 1,2-metalate rearrangement. Thus, the cyclobutyl TIB ester occupies a “Goldilocks zone,” being small enough for deprotonation and large enough to enable 1,2-migration. The generality of the reaction was explored with a broad range of boronic esters.