2-(2-Allylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2-Allylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 857934-92-0
• Molecular Formula: C₁₅H₂₁BO₂
• Molecular Weight: 244.142
• European Community (EC) Number: 853-920-7
• Nikkaji Number: J2.190.605K
• Mol file: 857934-92-0.mol

Synonyms:857934-92-0;2-(2-Allylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;(2-allylphenyl)boronic acid pinacol ester;4,4,5,5-tetramethyl-2-(2-prop-2-enylphenyl)-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-[2-(prop-2-en-1-yl)phenyl]-1,3,2-dioxaborolane;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(2-propenyl)phenyl]-;EN300-12732073

Chemical Property of 2-(2-Allylphenyl)-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: 296

Purity/Quality:

97% ^*data from raw suppliers

2-(2-Allylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2CC=C

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

There total 8 articles about 2-(2-Allylphenyl)-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: 84.0%

1-Bromo-2-iodobenzene (583-55-1) + allyl bromide (106-95-6) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[2-(2-propenyl)phenyl]-1,3,2-dioxaborolane (857934-92-0)

Guidance literature:

bis(pinacol)diborane; With dimethyl zinc(II); magnesium 2-methylpropan-2-olate; In 1,4-dioxane; hexane; at 0 - 20 ℃; for 0.5h; Schlenk technique; Glovebox; Inert atmosphere;

1-Bromo-2-iodobenzene; In 1,4-dioxane; hexane; at 20 - 120 ℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere;

allyl bromide; In 1,4-dioxane; hexane; at 20 - 75 ℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;

DOI:10.1021/ja409748m

Reference yield: 81.0%

1,2-Diiodobenzene (615-42-9) + allyl bromide (106-95-6) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[2-(2-propenyl)phenyl]-1,3,2-dioxaborolane (857934-92-0)

Guidance literature:

bis(pinacol)diborane; With dimethyl zinc(II); magnesium 2-methylpropan-2-olate; In 1,4-dioxane; hexane; at 0 - 20 ℃; for 0.5h; Schlenk technique; Glovebox; Inert atmosphere;

1,2-Diiodobenzene; In 1,4-dioxane; hexane; at 20 - 120 ℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere;

allyl bromide; In 1,4-dioxane; hexane; at 20 - 75 ℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;

DOI:10.1021/ja409748m

Reference yield: 76.0%

BO2(C(CH3)2)2(C6H4MgCl) + allyl bromide (106-95-6) → 4,4,5,5-tetramethyl-2-[2-(2-propenyl)phenyl]-1,3,2-dioxaborolane (857934-92-0)

Guidance literature:

copper(I) cyanide di(lithium chloride); In not given; reaction of BO2(C(CH3)2)2(C6H4MgCl) and CH2CHCH2Br transmetalated with CuCN*2LiCl;

DOI:10.1002/anie.200462928

upstream raw materials:

2-(2-iodophenyl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane

allyl bromide

2,3-dimethyl-2,3-butane diol

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

Downstream raw materials:

(2-allylphenyl)boronic acid