2-(2-Phenyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2-Phenyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 182810-44-2
• Molecular Formula: C₁₅H₂₁BO₂
• Molecular Weight: 244.142
• DSSTox Substance ID: DTXSID40455873
• Nikkaji Number: J772.711I
• Wikidata: Q82278027
• Mol file: 182810-44-2.mol

Synonyms:AGN-PC-0NG6JV;SCHEMBL15242529;DTXSID40455873;182810-44-2;2-(2-Phenyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-(2-Phenyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 244.1634601
• Heavy Atom Count: 18
• Complexity: 301

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 2-(2-Phenyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 4 articles about 2-(2-Phenyl-2-propenyl)-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: 74.0%

3-hydroxy-2-phenylpropene (6006-81-1) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(2-phenylallyl)-1,3,2-dioxaborolane (182810-44-2)

Guidance literature:

With CuCl; C₃H₂N₂Ph₂(C₆H₃MePh)(C₆H₄SO₃); NaOtBu; In tetrahydrofuran; methanol; -15°C;48 h;

DOI:10.1002/anie.201102398

Reference yield:

3-bromo-2-phenylprop-1-ene (3360-54-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-(2-phenylallyl)-1,3,2-dioxaborolane (182810-44-2)

Guidance literature:

With magnesium; In tetrahydrofuran; at 25 ℃; for 2.08333h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b01927

Reference yield:

isopropenylbenzene (98-83-9,6144-04-3,25014-31-7,42612-14-6) → 4,4,5,5-tetramethyl-2-(2-phenylallyl)-1,3,2-dioxaborolane (182810-44-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide / chloroform / Reflux

2: magnesium / tetrahydrofuran / 2.08 h / 25 °C / Inert atmosphere

With N-Bromosuccinimide; magnesium; In tetrahydrofuran; chloroform;

DOI:10.1021/acs.orglett.5b01927

upstream raw materials:

3-hydroxy-2-phenylpropene

bis(pinacol)diborane

isopropenylbenzene

3-bromo-2-phenylprop-1-ene

Downstream raw materials:

2-(2-phenyl-2-methylethyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane

C₂₀H₂₀O₂

(S)-N-(1,3-diphenylbut-3-en-1-yl)-P,P-diphenylphosphinic amide