915703-83-2

Basic information

• Product Name: [(CH)₂(N(2,6-iPr₂C₆H₃))₂]BH
• Synonyms: [(CH)₂(N(2,6-iPr₂C₆H₃))₂]BH
• CAS NO: 915703-83-2
• Molecular Weight: 388.404
• Mol File: 915703-83-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: [(CH)₂(N(2,6-iPr₂C₆H₃))₂]BH(CAS DataBase Reference)
• NIST Chemistry Reference: [(CH)₂(N(2,6-iPr₂C₆H₃))₂]BH(915703-83-2)
• EPA Substance Registry System: [(CH)₂(N(2,6-iPr₂C₆H₃))₂]BH(915703-83-2)

Safety Data

• Hazardous Substances Data: 915703-83-2(Hazardous Substances Data)

Upstream product

• 948054-44-2 lithium 1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-1,3,2-diazaborol-2-ide 
• 100-52-7 benzaldehyde 
• 71-43-2 benzene 
• 915703-81-0 N,N'-bis(2,6-diisopropylphenyl)-2-bromo-2,3-dihydro-1H-1,3,2-diazaborole 
• 10025-78-2 trichlorosilane 
• 74-94-2 dimethylamine borane 
• 7699-45-8 zinc dibromide 
• 7646-85-7 zinc(II) chloride 
• 7664-41-7 ammonia 
• 1333-74-0 hydrogen 
• 1082608-12-5 C₂H₂N₂BI(2,6-(iPr)2C₆H₃)2 
• 1008748-17-1 N,N'-bis(2,6-diisopropylphenyl)-2-chloro-1,3,2-diazaborole 
• 134750-23-5 N,N'-bis(2,6-diisopropylphenyl)-1,4-diaza-1,3-butadiene 

Downstream Products

• 1082608-24-9 PhCH₂[B(NDipCH)₂] 

Relevant articles and documents

Synthesis, structure of borylmagnesium, and its reaction with benzaldehyde to form benzoylborane

The reaction of boryllithium 2 with 1.0 or 0.5 equiv of MgBr2·OEt2 provided boryl Grignard reagents, borylmagnesium bromides 3 and 4, or bis(boryl)magnesium 5. Structures of 3, 4, and 5 in the crystals and solutions indicated the ionic character of the B-

Approaching a “Naked” Boryl Anion: Amide Metathesis as a Route to Calcium, Strontium, and Potassium Boryl Complexes

Amide metathesis has been used to generate the first structurally characterized boryl complexes of calcium and strontium, {(Me3Si)2N}M{B(NDippCH)2}(thf)n (M=Ca, n=2; M=Sr, n=3), through the reactions of the corresponding bis(amides), M{N(SiMe3)2}2(thf)2, with (thf)2Li- {B(NDippCH)2}. Most notably, this approach can also be applied to the analogous potassium amide K{N(SiMe3)2}, leading to the formation of the solvent-free borylpotassium dimer [K{B(NDippCH)2}]2, which is stable in the solid state at room temperature for extended periods (48 h). A dimeric structure has been determined crystallographically in which the K+ cations interact weakly with both the ipso-carbons of the flanking Dipp groups and the boron centres of the diazaborolyl heterocycles, with K???B distances of >3.1 ?. These structural features, together with atoms in molecules (QTAIM) calculations imply that the boron-containing fragment closely approaches a limiting description as a “free” boryl anion in the condensed phase.

An Acid-Free Anionic Oxoborane Isoelectronic with Carbonyl: Facile Access and Transfer of a Terminal B=O Double Bond

We disclose the synthesis and structural characterization of the first acid-free anionic oxoborane, [K(2.2.2-crypt)][(HCDippN)2BO] (1) (Dipp = 2,6-iPr2C6H3), which is isoelectronic with classical carbonyl compounds. 1 can readily be accessed from its borinic acid by a simple deprotonation/sequestration sequence. Crystallographic and density functional theory (DFT) analyses support the presence of a polarized terminal B?O double bond. Subsequent π bond metathesis converts the B?O bond to a heavier B?S containing system, affording the first anionic thioxoborane [K(2.2.2-crypt)][(HCDippN)2BS] (2), isoelectronic with thiocarbonyls. Facile B=O bond cleavage can also be achieved to access B-H and B-Cl bonds and, via a remarkable oxide (O2-) ion abstraction, to generate a borenium cation [(HCDippN)2B(NC5H5)][OTf] (4). By extension, 1 can act as an oxide transfer agent to organic substrates, a synthetic role traditionally associated with transition-metal compounds. Hence we show that B-O linkages, which are often considered to be thermodynamic sinks, can be activated under mild conditions toward bond cleavage and transfer, by exploiting the higher reactivity inherent in the B=O double bond.

A Combined Experimental/Computational Study of the Mechanism of a Palladium-Catalyzed Bora-Negishi Reaction

Experimental and computational efforts are reported which illuminate the mechanism of a novel boron version of the widespread Negishi coupling reaction that offers a new protocol for the formation of aryl/acyl C?B bonds using a bulky boryl fragment. The role of nucleophilic borylzinc reagents in the reduction of the PdII pre-catalysts to Pd0 active species has been demonstrated. The non-innocent behavior of the PPh3 ligands of the [Pd(PPh3)2Cl2] pre-catalyst under activation conditions has been probed both experimentally and computationally, revealing the formation of a trimetallic Pd species bearing bridging phosphide (PPh2?) ligands. Our studies also reveal the monoligated formulation of the Pd0 active species, which led us to synthesize related (η3-indenyl)Pd-monophosphine catalysts which show improved catalytic performances under mild conditions. A complete mechanistic proposal to aid future catalyst developments is provided.