4,4,5,5-Tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane
• CAS No.: 338998-93-9
• Molecular Formula: C11H17BO3
• Molecular Weight: 208.065
• Hs Code.: 2934999090
• European Community (EC) Number: 843-920-5
• DSSTox Substance ID: DTXSID30371674
• Nikkaji Number: J1.960.660K
• Wikidata: Q72491001
• Mol file: 338998-93-9.mol

Synonyms:338998-93-9;4,4,5,5-tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane;5-Methylfuran-2-boronic acid pinacol ester;2-Methylfurane-5-boronic acid pinacol ester;5-Methylfuran-2-boronic acid, pinacol ester;MFCD03094689;(5-METHYLFURAN-2-YL)BORONIC ACID PINACOL ESTER;5-Methyl-2-furanboronic acid pinacol ester;4,4,5,5-tetramethyl-2-(5-methyl-2-furyl)-1,3,2-dioxaborolane;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(5-methyl-2-furanyl)-;2-Methylfurane-5-boronicacidpinacolester;2-METHYLFURAN-5-BORONIC ACID PINACOL ESTER;SCHEMBL482469;DTXSID30371674;FNPZFZKLYGWKLH-UHFFFAOYSA-N;4,4,5,5-TETRAMETHYL-2-(5-METHYL-2-FURANYL)-1,3,2-DIOXABOROLANE;AKOS004113937;AB13349;CS-W004966;5-METHYLFURAN-2-BORONIC ACID P;5-methyl-2-furanboronicacid pinacol ester;AS-18705;SY025286;5-methyl-2-furyl boronic acid pinacol ester;A6005;FT-0763295;T3582;EN300-191678;5-Methyl-2-furanboronic acid pinacol ester, 95%;J-019366;5-METHYLFURAN-2-BORONIC ACID PINACOL ESTER 95%;Z1509631831;2-(5-Methyl-2-furyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan;4,4,5,5-Tetramethyl-2-(5-methyl-furan-2-yl)-[1,3,2]dioxaborolane;5-METHYL-2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXOBOROLAN-2-YL)FURAN,2-(5-METHYLFUR-2-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

Chemical Property of 4,4,5,5-Tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.00748mmHg at 25°C
• Refractive Index: 1.468
• Boiling Point: 277.794 °C at 760 mmHg
• Flash Point: 121.806 °C
• PSA: 31.60000
• Density: 1.02 g/cm³
• LogP: 1.88720
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 208.1270746
• Heavy Atom Count: 15
• Complexity: 236

Purity/Quality:

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

5-Methyl-2-furanboronic acid pinacol ester ^*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)C
• Uses: 5-Methyl-2-furanboronic Acid Pinacol Ester is used as a reagent for the borylation of furans, pyrroles and other organic reactions.

Technology Process of 4,4,5,5-Tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane

There total 11 articles about 4,4,5,5-Tetramethyl-2-(5-methylfuran-2-yl)-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%

2-methylfuran (534-22-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane (338998-93-9)

Guidance literature:

With (^CyAPDI)CoCH₃; In neat (no solvent); at 23 ℃; for 72h; Reagent/catalyst; Temperature;

Reference yield: 98.0%

2-methylfuran (534-22-5) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane (338998-93-9)

Guidance literature:

With C₂₉H₃₀CoN₄O₄; lithium methanolate; In neat (no solvent); at 80 ℃; for 24h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.organomet.6b00630

Reference yield: 80.0%

→ 4,4,5,5-tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane (338998-93-9)

Guidance literature:

With 1-(2-borylphenyl)-2,2,6,6-tetramethylpiperidine dimer; In chloroform; at 80 ℃; for 16h; Sealed tube; Microwave irradiation; Glovebox; Inert atmosphere;

upstream raw materials:

2-methylfuran

bis(pinacol)diborane

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

deutero-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

CM-272

(S)-7-(5-methylfuran-2-yl)-3-((6-(([tetrahydrofuran-3-yl]oxy)methyl)pyridin-2-yl)methyl)-3H-[1,2,3 ]triazolo[4,5-d]pyrimidin-5-amine

Refernces

• 1、 Donnelly, Liam J.,Faber, Teresa,Morrison, Carole A.,Nichol, Gary S.,Thomas, Stephen P.,Love, Jason B.. "C-H Borylation Catalysis of Heteroaromatics by a Rhenium Boryl Polyhydride". . p. 7394 - 7400. Retrieved 2021/06/30.
• 2、 Arevalo, Rebeca,Pabst, Tyler P.,Chirik, Paul J.. "C(sp2)-H Borylation of Heterocycles by Well-Defined Bis(silylene)pyridine Cobalt(III) Precatalysts: Pincer Modification, C(sp2)-H Activation, and Catalytically Relevant Intermediates". supporting information. p. 2763 - 2773. Retrieved 2020/07/24.