Furan-2,5-diboronic acid, pinacol ester

Base Information

• Chemical Name: Furan-2,5-diboronic acid, pinacol ester
• CAS No.: 476004-83-8
• Molecular Formula: C₁₆H₂₆B₂O₅
• Molecular Weight: 320.001
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60478448
• Nikkaji Number: J1.768.879K
• Wikidata: Q82311836
• Mol file: 476004-83-8.mol

Synonyms:476004-83-8;Furan-2,5-diboronic acid, pinacol ester;2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan;4,4,5,5-TETRAMETHYL-2-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FURAN-2-YL]-1,3,2-DIOXABOROLANE;SCHEMBL240284;DTXSID60478448;MFCD11504967;AKOS025293537;Furan-2,5-diboronic acid,pinacol ester;BS-28563;CS-0175029;A872113

Chemical Property of Furan-2,5-diboronic acid, pinacol ester

Chemical Property:

• PSA: 50.06000
• LogP: 1.87800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 320.1966343
• Heavy Atom Count: 23
• Complexity: 403

Purity/Quality:

97% ^*data from raw suppliers

(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-yl)boronicacid 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=C(O2)B3OC(C(O3)(C)C)(C)C

Technology Process of Furan-2,5-diboronic acid, pinacol ester

There total 9 articles about Furan-2,5-diboronic acid, pinacol ester 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%

furan (110-00-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan (476004-83-8)

Guidance literature:

With (^iPrPNP)CoCH₂SiMe₃; In neat (no solvent); at 23 ℃; for 10h;

Reference yield: 85.0%

furan (110-00-9) + bis(pinacol)diborane (73183-34-3) → 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan (476004-83-8)

Guidance literature:

With C₃₉H₅₉Br₂CoN₇Si₂; sodium triethylborohydride; cyclohexene; In tetrahydrofuran; at 100 ℃; for 24h; regioselective reaction; Inert atmosphere; Schlenk technique; Glovebox;

DOI:10.1002/chem.201605937

Reference yield: 76.0%

furan (110-00-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-furan-2-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (374790-93-9) + 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan (476004-83-8)

Guidance literature:

With (^CyAPDI)CoCH₃; In neat (no solvent); at 23 ℃; for 10h;

upstream raw materials:

furan

bis(pinacol)diborane

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

Refernces

• 1、 Britton, Luke,Docherty, Jamie H.,Dominey, Andrew P.,Thomas, Stephen P.. "Iron-catalysed C(sp2)-H borylation enabled by carboxylate activation". supporting information. . Retrieved 2020/02/22.
• 2、 Ren, Hailong,Zhou, Yu-Peng,Bai, Yunping,Cui, Chunming,Driess, Matthias. "Cobalt-Catalyzed Regioselective Borylation of Arenes: N-Heterocyclic Silylene as an Electron Donor in the Metal-Mediated Activation of C?H Bonds". supporting information. p. 5663 - 5667. Retrieved 2017/04/28.