2-(Benzofuran-2-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(Benzofuran-2-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 402503-13-3
• Molecular Formula: C14H17BO3
• Molecular Weight: 244.098
• Hs Code.: 2934999090
• European Community (EC) Number: 941-104-4,889-614-5
• DSSTox Substance ID: DTXSID30463785
• Nikkaji Number: J1.635.711A
• Wikidata: Q82288819
• Mol file: 402503-13-3.mol

Synonyms:402503-13-3;2-(BENZOFURAN-2-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;Benzofuran-2-boronic acid, pinacol ester;2-(1-benzofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Benzofuran-2-boronic acid pinacol ester;Benzofuran-2-boronic acid,pinacol ester;SCHEMBL824095;DTXSID30463785;GVWNFCUCNAWDNO-UHFFFAOYSA-N;1,3,2-Dioxaborolane, 2-(2-benzofuranyl)-4,4,5,5-tetramethyl-;MFCD11870258;AKOS016000704;AS-2632;2-Benzofuran-2-boronic acid pinacol ester;CS-0091643;FT-0726845;EN300-705935;BENZOFURAN-2-YLBORONIC ACID PINACOL ESTER;Z1742195735;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran

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

Chemical Property:

• Boiling Point: 340.0±15.0 °C(Predicted)
• PSA: 31.60000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 2.73200
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 244.1270746
• Heavy Atom Count: 18
• Complexity: 313

Purity/Quality:

98%,99%, ^*data from raw suppliers

Benzofuran-2-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=CC=CC=C3O2

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

There total 17 articles about 2-(Benzofuran-2-YL)-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%

2.3-dihydrobenzofuran (496-16-2) + bis(pinacol)diborane (73183-34-3) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan (402503-13-3)

Guidance literature:

With C₂₅H₄₀O₂P₂Ru; In octane; at 150 ℃; for 12h; Inert atmosphere;

Reference yield: 99.0%

1-benzofurane (271-89-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan (402503-13-3)

Guidance literature:

With 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In hexane; at 25 ℃; for 1h;

DOI:10.1039/b311103b

Reference yield: 93.0%

1-benzofurane (271-89-6) + bis(pinacol)diborane (73183-34-3) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]furan (402503-13-3)

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 50 ℃; for 16h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.5b05252

upstream raw materials:

2-chlorobenzo[b]furan

bis(pinacol)diborane

1-benzofurane

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

Downstream raw materials:

2-(3-phenylpropyl)benzo[b]furan

(3,6-bis[5-(benzofuran-2-yl)-thiophen-2-yl]-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione)

2-(2-benzofuranyl)-benzonitrile

4-(1-benzofuran-2-yl)benzonitrile

Refernces

• 1、 Akhtar, Naved,Antil, Neha,Balendra,Begum, Wahida,Chauhan, Manav,Gupta, Poorvi,Kumar, Ajay,Malik, Jaideep,Manna, Kuntal,Newar, Rajashree. "Mono-Phosphine Metal-Organic Framework-Supported Cobalt Catalyst for Efficient Borylation Reactions". supporting information. . Retrieved 2022/03/15.
• 2、 Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul. "Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates". supporting information. p. 5022 - 5037. Retrieved 2021/05/04.