2-[3-Bromo-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-[3-Bromo-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 479411-92-2
• Molecular Formula: C13H15BBrF3O2
• Molecular Weight: 350.971
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID40462108
• Nikkaji Number: J1.803.291K
• Mol file: 479411-92-2.mol

Synonyms:479411-92-2;2-[3-bromo-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(3-BROMO-5-(TRIFLUOROMETHYL)PHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;3-Bromo-5-(trifluoromethyl)benzeneboronic acid pinacol ester;DTXSID40462108;MFCD12405333;AKOS017347034;AS-42746;A872012;(3-BROMO-5-(TRIFLUOROMETHYL)PHENYL)BORONIC ACID PINACOL ESTER

Chemical Property of 2-[3-Bromo-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Melting Point: 50-52℃
• Boiling Point: 333.8±42.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.40±0.1 g/cm3(Predicted)
• LogP: 3.76710
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 350.03006
• Heavy Atom Count: 20
• Complexity: 357

Purity/Quality:

98.5% ^*data from raw suppliers

2-(3-Bromo-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC(=C2)Br)C(F)(F)F
• Uses: Used as a active pharmaceutical ingredient.

Technology Process of 2-[3-Bromo-5-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 2 articles about 2-[3-Bromo-5-(trifluoromethyl)phenyl]-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: 99.0%

3-bromo-1-trifluoromethylbenzene (401-78-5) + bis(pinacol)diborane (73183-34-3) → 2-(3-bromo-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (479411-92-2)

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: 93.0%

3-bromo-1-trifluoromethylbenzene (401-78-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(3-bromo-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (479411-92-2)

Guidance literature:

With 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; at 80 ℃; for 2h;

DOI:10.1021/ol060207i

Reference yield: 78.0%

acetamide (60-35-5) + 2-(3-bromo-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (479411-92-2) → N-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethylphenyl]acetamide

Guidance literature:

With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1,4-dioxane; at 80 ℃; for 3.5h;

DOI:10.1021/ol060207i

upstream raw materials:

3-bromo-1-trifluoromethylbenzene

bis(pinacol)diborane

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

Downstream raw materials:

3,6-bis(trifluoromethyl)bromobenzene

1-bromo-3-nitro-5-(trifluoromethyl)benzene

3-(trifluoromethyl)biphenyl

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、 Tahir, Norini,Muniz-Miranda, Francesco,Everaert, Jonas,Tack, Pieter,Heugebaert, Thomas,Leus, Karen,Vincze, Laszlo,Stevens, Christian V.,Van Speybroeck, Veronique,Van Der Voort, Pascal. "Immobilization of Ir(I) complex on covalent triazine frameworks for C–H borylation reactions: A combined experimental and computational study". . p. 135 - 143. Retrieved 2019/02/12.