390381-02-9

Basic information

• Product Name: 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(2-methylphenyl)methyl]-
• CAS NO: 390381-02-9
• Molecular Formula: C14H21BO2
• Molecular Weight: 232.131
• Mol File: 390381-02-9.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(2-methylphenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(2-methylphenyl)methyl]-(390381-02-9)
• EPA Substance Registry System: 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(2-methylphenyl)methyl]-(390381-02-9)

Safety Data

• Hazardous Substances Data: 390381-02-9(Hazardous Substances Data)

Usage

Type of compound

Organic compound

Category

Boronic acid derivative

Application

Used in organic synthesis as a reagent for Suzuki-Miyaura cross-coupling reactions

Physical state

Colorless liquid

Boiling point

High boiling point

Storage conditions

Typically handled and stored in air-free conditions

Sensitivity

Sensitive to air and moisture

Importance

Important intermediate in the production of pharmaceuticals and fine chemicals

Unique properties

Valuable in the field of organic chemistry due to its unique chemical properties

Upstream product

• 552-45-4 1-chloromethyl-2-methylbenzene 
• 73183-34-3 bis(pinacol)diborane 
• 95-47-6 o-xylene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 17373-93-2 2-methylbenzyl acetate 
• 4525-48-8 N,N-dimethyl(2-methylbenzyl)amine 
• 95-46-5 2-methylphenyl bromide 
• 78782-17-9 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane 
• 89-92-9 2-methylbenzyl bromide 

Downstream Products

• 1373432-91-7 C₂₈H₃₁N₃O₃ 

Relevant articles and documents

C(sp3)-H selective benzylic borylation by in situ reduced ultrasmall Ni species on CeO2

Herein, we report that highly dispersed Ni hydroxide species supported on CeO2 act as an efficient heterogeneous catalyst for the selective borylation of benzylic C(sp3)-H bonds of alkylarenes including secondary derivatives, using pinacolborane as the bo

Efficient synthesis of alkylboronic esters: Via magnetically recoverable copper nanoparticle-catalyzed borylation of alkyl chlorides and bromides

We report a magnetically separable Cu nanocatalyst (Fe-DOPA-Cu) for the borylation of alkyl halides with alkoxy diboron reagents, providing alkylboronic esters in high yields, with broad functional group tolerance under mild reaction conditions. The procedure is also applicable to the borylation of benzyl chlorides and bromides. Radical clock experiments support a radical-mediated process. Easy recycling of the catalyst resulted in no significant loss of activity up to ten runs.

Making Dimethylamino a Transformable Directing Group by Nickel-Catalyzed C-N Borylation

The dimethylamino (Me2N) group is arguably the most versatile functional group capable of highly efficient and site-selective directed aromatic functionalizations at the ortho-, meta-, and para-positions depending on reaction conditions. While the repertoire of Me2N-directed reactions is growing at a rapid pace, the lack of a general method to transform this group to other functionalities hampers its wider application in organic synthesis. Here we report nickel-catalyzed C-N borylations of aryl- and benzyl-dimethylamines that permit the conversion of a huge library of largely underutilized Me2N-containing organic molecules into various functional molecules by taking advantage of the wealth of existing C-B functionalization methods.