129636-11-9

Basic information

• Product Name: DIMETHYL-[2-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE
• Synonyms: DIMETHYL-[2-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE;2-(N,N-Dimethylaminomethyl)phenylboronic acid,pinacol ester;N,N-Dimethyl-1-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine
• CAS NO: 129636-11-9
• Molecular Formula: C15H24BNO2
• Molecular Weight: 261.17
• Mol File: 129636-11-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 340.5±25.0 °C(Predicted)
• Appearance: /
• Density: 1.00±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 8.87±0.28(Predicted)
• CAS DataBase Reference: DIMETHYL-[2-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL-[2-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE(129636-11-9)
• EPA Substance Registry System: DIMETHYL-[2-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZYL]-AMINE(129636-11-9)

Safety Data

• Hazardous Substances Data: 129636-11-9(Hazardous Substances Data)

Usage

Uses

2-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol ester

Upstream product

• 103-83-3 N,N'-dimethylbenzylamine 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 120-65-0 ortho-dimethylaminomethylphenol 

Relevant articles and documents

Aluminabenzene-Rh and -Ir Complexes: Synthesis, Structure, and Application toward Catalytic C-H Borylation

Aluminabenzene-rhodium and -iridium complexes were synthesized, in which the aluminum atom played as a proximal Lewis acidic site. Based on their structural analysis, aluminabenzene ligand could coordinate to Rh and Ir as a η5-pentadienyl ligand. The Lewis acidic character of aluminum atom in aluminabenzene ligand was confirmed by treatment with 4-dimethylaminopyridine to form the corresponding Lewis acid-base complexes. In addition, the α-selective C-H borylation of triethylamine with the aluminabenzene-ligated iridium catalyst was demonstrated.

Photo-Induced ortho-C-H Borylation of Arenes through in Situ Generation of Rhodium(II) Ate Complexes

Photoinduced in situ "oxidation"of half-sandwich metal complexes to "high-valent"cationic metal complexes has been used to accelerate catalytic reactions. Here, we report the unprecedented photoinduced in situ "reduction"of half-sandwich metal [Rh(III)] complexes to "low-valent"anionic metal [Rh(II)] ate complexes, which facilitate ligand exchange with electron-deficient elements (diboron). This strategy was realized by using a functionalized cyclopentadienyl (CpA3) Rh(III) catalyst we developed, which enabled the basic group-directed room temperature ortho-C-H borylation of arenes.

Iridium-catalyzed, substrate-directed C-H borylation reactions of benzylic amines

The iridium-catalyzed arene C-H borylation reaction of benzylic amines has been developed, which inverts the typical steric-controlled product distribution to provide ortho-substituted boronate esters. Picolylamine was found to be an ideal ligand to replace 4,4′-di-tert-butylbipyridine to induce the directing effect. Preliminary experiments are consistent with a mechanism involving dissociation of one amine of the hemilabile diamine ligand.