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

Base Information

• Chemical Name: 2-(3,5-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 408492-26-2
• Molecular Formula: C12H15BBr2O2
• Molecular Weight: 361.869
• Hs Code.: 2934999090
• European Community (EC) Number: 805-540-8
• DSSTox Substance ID: DTXSID50700028
• Nikkaji Number: J1.689.013H
• Wikidata: Q82631189
• Mol file: 408492-26-2.mol

Synonyms:408492-26-2;2-(3,5-dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(3,5-DIBROMOPHENYL) 4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;3,5-Dibromophenylboronic acid pinacol ester;SCHEMBL14907354;DTXSID50700028;MFCD12407202;AKOS025392322;AS-2571;CS-0175566;E85424;EN300-7405731;A914350

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

Chemical Property:

• Boiling Point: 377.8±32.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.56±0.1 g/cm3(Predicted)
• LogP: 3.51080
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 361.95114
• Heavy Atom Count: 17
• Complexity: 270

Purity/Quality:

98% ^*data from raw suppliers

2-(3,5-Dibromophenyl)4,4,5,5-tetramethyl-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)Br)Br
• Uses: 2-(3,5-Dibromophenyl) 4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

There total 3 articles about 2-(3,5-Dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1,3-dibromobenzene (108-36-1) + bis(pinacol)diborane (73183-34-3) → 2-(3,5-dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (408492-26-2)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole; at 100 ℃; for 16h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.5b05252

Reference yield:

1,3,5-trisbromobenzene (626-39-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,2-dioxaborolane (196212-27-8) + 1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (365564-05-2) + (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene) (594823-67-3) + 2-(3,5-dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (408492-26-2)

Guidance literature:

With (CF₃SO₂)2NLi; In tetrahydrofuran; Electrolysis; electrolysis (2 F/mol) with Mg anode under inert atm. at room temp. at 30 mA; after electrolysis, solvent evapd. under vac.; slowly hydrolysed at 0°C with soln. of H2SO4 until pH 5; further products: C6H3(B(OC(CH3)2C(CH3)2O))2Br; purified by column chromy. on silica gel (pentane/ether);

DOI:10.1016/j.electacta.2004.12.049

Reference yield:

1,3-dibromobenzene (108-36-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(3,5-dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (408492-26-2)

Guidance literature:

With (η⁵-indenyl)(η⁴-1,5-cyclooctadiene)iridium(I); 1,2-bis-(diphenylphosphino)ethane; In cyclohexane; at 100 ℃; for 18h;

DOI:10.1021/ja0349857

upstream raw materials:

1,3-dibromobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

bis(pinacol)diborane

1,3,5-trisbromobenzene

Downstream raw materials:

3,3',5,5'-tetrabromo-1,1'-biphenyl

3,5-dibromonitrobenzene

2-(3,5-dibromophenyl)-4,6-diphenylpyrimidine

1,3-dibromo-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Refernces

• 1、 Slack, Eric D.,Colacot, Thomas J.. "Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics". supporting information. p. 1561 - 1565. Retrieved 2021/02/20.
• 2、 Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel. "meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation". supporting information. p. 8018 - 8023. Retrieved 2019/05/29.