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

Base Information

• Chemical Name: 2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 86308-26-1
• Molecular Formula: C6H13(C6H12BO2)(CH3)4
• Molecular Weight: 212.14
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50448433
• Nikkaji Number: J1.686.550H
• Wikidata: Q82267414
• Mol file: 86308-26-1.mol

Synonyms:86308-26-1;2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Hexylboronic acid pinacol ester;1-Hexylboronic acid pinacol ester;starbld0018991;1,3,2-Dioxaborolane, 2-hexyl-4,4,5,5-tetramethyl-;SCHEMBL15928015;DTXSID50448433;MFCD08457665;Hexylboronic acid pinacol ester, 97%;BS-51462;CS-0139357;E76883;EN300-1706423;2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborole

Chemical Property of 2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.067mmHg at 25°C
• Refractive Index: 1.426
• Boiling Point: 238.068°C at 760 mmHg
• Flash Point: 84 °C
• PSA: 18.46000
• Density: 1.167
• LogP: 3.65890
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 212.1947602
• Heavy Atom Count: 15
• Complexity: 186

Purity/Quality:

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

Hexylboronic acid pinacol ester 97% ^*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)CCCCCC

Technology Process of 2-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 4 articles about 2-Hexyl-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: 63.0%

iodobenzene (591-50-4) + 1-bromo-hexane (111-25-1) + bis(pinacol)diborane (73183-34-3) → 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + 2-hex-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (86308-26-1)

Guidance literature:

With catalyst: CuI/P(C₄H₉)3; LiOC(CH₃)3; In N,N-dimethyl-formamide; byproducts: C6H5C6H13; at 60°C for 24 h;

DOI:10.1002/anie.201106299

Reference yield: 55.0%

C16H23NO + bis(pinacol)diborane (73183-34-3) → 5-methoxy-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 2-hex-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (86308-26-1)

Guidance literature:

C₁₆H₂₃NO; bis(pinacol)diborane; With Trimethyl borate; triethylamine; In octane; at 160 ℃; for 48h;

With hydrogenchloride; In water; for 0.5h; regioselective reaction;

DOI:10.1039/d1sc04487g

Reference yield: 29.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 1-hexene (592-41-6,25067-06-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-[(1E)-hex-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (126688-97-9) + 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane (83947-56-2) + 4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane (174090-36-9) + 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane (165904-22-3) + 2-hex-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (86308-26-1)

Guidance literature:

chloro(1,5-cyclooctadiene)rhodium(I) dimer; In toluene; pinacolborane and vinylarene were added to a mixt. of Rh-complex in toluene under Ar, the mixt. was stirred at room temp. for 4 h; diluted with toluene, washed with water, dried over MgSO4, evapd., distilled with Kugelrohr or chromy. on silica gel;

DOI:10.1246/bcsj.75.825

upstream raw materials:

styrene

1-hexene

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

iodobenzene

Downstream raw materials:

hexan-1-ol

heptanal

2-hexylthiophene

hexylbenzene