2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1025707-93-0
• Molecular Formula: C8H12O2
• Molecular Weight: 210.081
• Hs Code.: 2932990090
• European Community (EC) Number: 864-932-7
• DSSTox Substance ID: DTXSID70585950
• Nikkaji Number: J2.588.631C
• Wikidata: Q82477971
• Mol file: 1025707-93-0.mol

Synonyms:1025707-93-0;2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3,4-DIHYDRO-2H-PYRAN-6-BORONIC ACID PINACOL ESTER;2H-Pyran, 3,4-dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;MFCD07368233;(3,4-DIHYDRO-2H-PYRAN-6-YL)BORONIC ACID PINACOL ESTER;SCHEMBL319623;DTXSID70585950;RNRIMDSCBRDPLC-UHFFFAOYSA-N;AKOS015999417;AB31957;FS-4746;SY066203;CS-0097347;EN300-170997;A896766;J-000727;Z1509595073;6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyran

Chemical Property of 2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Boiling Point: 240.9±50.0 °C(Predicted)
• Flash Point: 102℃
• PSA: 27.69000
• Density: 1.014 g/mL at 25 °C
• LogP: 2.31210
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 210.1427246
• Heavy Atom Count: 15
• Complexity: 268

Purity/Quality:

97% ^*data from raw suppliers

3,4-Dihydro-2H-pyran-6-boronic acid, pinacol ester 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=CCCCO2

Technology Process of 2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 2 articles about 2-(3,4-Dihydro-2H-pyran-6-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:

3,4-dihydro-2H-pyran (110-87-2) + bis(pinacol)diborane (73183-34-3) → 2-(5,6-dihydro-4H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1046811-99-7) + 2-(3,4-dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1025707-93-0)

Guidance literature:

With 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In octane; at 80 ℃; for 8h; Title compound not separated from byproducts.;

DOI:10.1246/cl.2008.664

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(5,6-dihydro-4H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1046811-99-7) + 2-(3,4-dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1025707-93-0)

Guidance literature:

With catalyst:(Ir(COD)OCH₃)2/2(4,4'-di-tert-butyl-bipy); In hexane; heating in hexane at 25-80°C in the presence of (Ir(OMe)(COD))2/2(4,4'-di-tert-butyl-bipy); (.alpha/β=95/5);

DOI:10.1246/bcsj.81.1535

Reference yield: 97.0%

2-(3,4-dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1025707-93-0) + (Z)-3-bromo-3-phenyl-2-propen-1-ol → 4-(3-phenyl-2-furyl)-1-butanol (1447908-71-5)

Guidance literature:

2-(3,4-dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; (Z)-3-bromo-3-phenyl-2-propen-1-ol; With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydroxide; In 1,4-dioxane; water; at 100 ℃; for 0.166667h; Microwave irradiation; Inert atmosphere; Sealed tube;

With p-toluenesulfonic acid monohydrate; In 1,4-dioxane; water; at 20 ℃; for 0.166667h;

DOI:10.1021/ol4014574

upstream raw materials:

3,4-dihydro-2H-pyran

bis(pinacol)diborane

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

Downstream raw materials:

5,6-dimethoxy-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]

(2-(3,4-dihydro-2H-pyran-6-yl)phenyl)methanol

3′,4′,5′,6′-tetrahydro-spiro[isobenzofuran-1(3H),2′(2H)pyran]

3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-5-yl 4-methylbenzenesulfonate