2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole

Base Information

• Chemical Name: 2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole
• CAS No.: 26071-86-3
• Molecular Formula: C₂₀H₁₄B₂O₄
• Molecular Weight: 339.951
• Mol file: 26071-86-3.mol

Synonyms:

Chemical Property of 2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole

There total 8 articles about 2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole 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:

2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) + (E)-2-(2'-phenylethenyl)-1,3,2-benzodioxaborole (6783-04-6,57001-92-0,96794-40-0) → 2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole (26071-86-3) + (C6H4O2B)2CHCH2C6H5 + 2,2'-(1-phenylethane-1,2-diyl)dibenzo[1,3,2]dioxaborole (215254-67-4) + (C6H4O2B)2CHCH(BO2C6H4)C6H5 + (C6H4O2B)3CCH2C6H5

Guidance literature:

Wilkinson's catalyst; In tetrahydrofuran; under N2, standard Schlenk techniques; soln. of (C6H4O2B)2, styrylboronate ester and Rh complex (molar ratio 1:1:0.01) in THF heated in sealed tube at 58°C for 12 h; cooled to room temp.; solvent removed in vac.; dissolved in CDCl3; product distribution detd. by (1)H NMR spectra;

DOI:10.1016/S0022-328X(02)01310-4

Reference yield:

2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) + (E)-2-(2'-phenylethenyl)-1,3,2-benzodioxaborole (6783-04-6,57001-92-0,96794-40-0) → 2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole (26071-86-3) + (C6H4O2B)2CHCH2C6H5 + (C6H4O2B)2CHCH(BO2C6H4)C6H5 + (C6H4O2B)3CCH2C6H5

Guidance literature:

With catalyst: (Rh(cyclooctene)2(μ-Cl))2-P(o-tol)3; In tetrahydrofuran; under N2, standard Schlenk techniques; soln. of (C6H4O2B)2, styrylboronate ester and Rh complex+(2-4)P(o-tol)3 catalyst (molar ratio 1:1:0.01) in THF heated in sealed tube at 58°C for 12 h; cooled to room temp.; solvent removed in vac.; dissolved in CDCl3; product distribution detd. by (1)H NMR spectra;

DOI:10.1016/S0022-328X(02)01310-4

Reference yield:

phenylacetylene (536-74-3) → 2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole (26071-86-3) + (C6H4O2B)2CHCH2C6H5 + (C6H4O2B)2CHCH(BO2C6H4)C6H5 + (C6H4O2B)3CCH2C6H5

Guidance literature:

Multi-step reaction with 2 steps

1: BH₃ / neat (no solvent)

2: catalyst: (Rh(C8H14)2(μ-Cl))2-P(o-tol)3-B2cat2 / tetrahydrofuran

With BH₃; catalyst: (Rh(C8H14)2(μ-Cl))2-P(o-tol)3-B2cat2; In tetrahydrofuran;

DOI:10.1016/S0022-328X(02)01310-4

upstream raw materials:

tetrakis(dimethoxyboryl)methane

benzaldehyde

benzene-1,2-diol

2,2'-bis(1,3,2-benzodioxaborole)