408492-26-2

Basic information

• Product Name: 2-(3,5-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(3,5-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 408492-26-2
• Molecular Formula: C₁₂H₁₅BBr₂O₂
• Molecular Weight: 361.8653
• Mol File: 408492-26-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 377.8±32.0 °C(Predicted)
• Appearance: /
• Density: 1.56±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2-(3,5-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,5-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(408492-26-2)
• EPA Substance Registry System: 2-(3,5-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(408492-26-2)

Safety Data

• Hazardous Substances Data: 408492-26-2(Hazardous Substances Data)

Usage

Uses

2-(3,5-Dibromophenyl) 4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Upstream product

• 108-36-1 1,3-dibromobenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 626-39-1 1,3,5-trisbromobenzene 

Downstream Products

• 16400-50-3 3,3',5,5'-tetrabromo-1,1'-biphenyl 
• 942132-67-4 2-(3,5-dibromophenyl)-4,6-diphenylpyrimidine 
• 626-41-5 3,5-dibromophenol 
• 6311-60-0 3,5-dibromonitrobenzene 
• 864736-96-9 1,3-dibromo-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene 
• 943137-95-9 5-[5-(3,5-dibromophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile 
• 663180-98-1 methyl 3',5'-dibromo-[1,1'-biphenyl]-4-carboxylate 

Relevant articles and documents

Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics

A newly developed robust catalyst [Ir(COD)(Phen)Cl] (A) was used for the C-H borylation of three dozen aromatics and heteroaromatics with excellent yield and selectivity. Activation of the catalyst was identified by the use of catalytic amounts of water, alcohols, etc., when B2pin2 was used in noncoordinating solvents, while for THF catalytic use of HBpin was required. The results were on par with the in situ based expensive system [Ir(OMe)(COD)]2/dtbbpy or Me4Phen.

Direct C?H Borylation of Arenes Catalyzed by Saturated Hydride-Boryl-Iridium-POP Complexes: Kinetic Analysis of the Elemental Steps

The saturated trihydride IrH3{κ3-P,O,P-[xant(PiPr2)2]} (1; xant(PiPr2)2=9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) activates the B?H bond of two molecules of pinacolborane (HBpin) to give H2, the hydride-boryl derivatives IrH2(Bpin){κ3-P,O,P-[xant(PiPr2)2]} (2) and IrH(Bpin)2{κ3-P,O,P-[xant(PiPr2)2]} (3) in a sequential manner. Complex 3 activates a C?H bond of two molecules of benzene to form PhBpin and regenerates 2 and 1, also in a sequential manner. Thus, complexes 1, 2, and 3 define two cycles for the catalytic direct C?H borylation of arenes with HBpin, which have dihydride 2 as a common intermediate. C?H bond activation of the arenes is the rate-determining step of both cycles, as the C?H oxidative addition to 3 is faster than to 2. The results from a kinetic study of the reactions of 1 and 2 with HBpin support a cooperative function of the hydride ligands in the B?H bond activation. The addition of the boron atom of the borane to a hydride facilitates the coordination of the B?H bond through the formation of κ1- and κ2-dihydrideborate intermediates.

Sterically controlled C-H/C-H homocoupling of arenes: Via C-H borylation

A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C-H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C-H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain via the Ullmann or the Suzuki coupling protocols. Finally, we have shown a one-pot sequence describing C-H borylation/Cu-catalyzed homocoupling/Pd-catalyzed Suzuki coupling to obtain π-extended arene frameworks.