(E)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane

Base Information

• Chemical Name: (E)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane
• CAS No.: 78782-27-1
• Molecular Formula: C14H19 B O2
• Molecular Weight: 230.115
• European Community (EC) Number: 641-148-1,848-539-8
• Nikkaji Number: J472.478J,J672.985A
• ChEMBL ID: CHEMBL2315711
• Mol file: 78782-27-1.mol

Synonyms:83947-56-2;78782-27-1;(E)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane;e-phenylethenylboronic acid, pinacol ester;4,4,5,5-tetramethyl-2-[(E)-2-phenylethenyl]-1,3,2-dioxaborolane;trans-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)styrene;beta-styrylboronic acid pinacol ester;E-Phenylethenylboronic acid pinacol ester;trans-2-Phenylvinylboronic acid pinacol ester;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(1E)-2-phenylethenyl]-;4,4,5,5-tetramethyl-2-[(e)-2-phenylvinyl]-1,3,2-dioxaborolane;E-Phenylethenylboronic acid,pinacol ester;MFCD03453666;trans-styrylboronic acid, pinacol ester;SCHEMBL1007719;SCHEMBL1007720;CHEMBL2315711;(E/Z)4,4,5,5-tetramethyl-2-styryl-1,3,2-dioxaborolane;ARAINKADEARZLZ-ZHACJKMWSA-N;AKOS015960064;GS-5850;6-Nitro-1-diazo-2-naphthol-4-sulfonicacid;(E)-Phenylethenylboronic acid, pinacol ester;(E)-STYRYLBORONIC ACID PINACOL ESTER;CS-0006605;CS-0437049;F11372;H10648;EN300-1270619;2-Styryl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;Z2312943806;2-trans-Styryl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane;(E)-4,4,5,5-TETRAMETHYL-2-(2-PHENYLVINYL)-1,3,2-DIOXABOROLANE;4,4,5,5-tetramethyl-2-[(1E)-2-phenylethenyl]-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-[(1Z)-2-phenylethenyl]-1,3,2-dioxaborolane;1,3,2-DIOXABOROLANE,4,4,5,5-TETRAMETHYL-2-[(1E)-2-PHENYLETHENYL]-

Chemical Property of (E)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane

Chemical Property:

• Melting Point: 27-33 °C(lit.)
• Boiling Point: 271.9±33.0 °C(Predicted)
• Flash Point: >230 °F
• PSA: 18.46000
• Density: 0.99±0.1 g/cm3(Predicted)
• LogP: 3.33120
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 230.1478100
• Heavy Atom Count: 17
• Complexity: 275

Purity/Quality:

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

4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane 95+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C=CC2=CC=CC=C2
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/C2=CC=CC=C2

Technology Process of (E)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane

There total 53 articles about (E)-4,4,5,5-Tetramethyl-2-styryl-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: 99.0%

phenylacetylene (536-74-3) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane (78782-27-1)

Guidance literature:

bis(pinacol)diborane; With methanol; copper(II) bis(trifluoromethanesulfonate); 2,6-bis(pyrazole)pyridine; sodium t-butanolate; In acetonitrile; for 0.5h; Inert atmosphere; Schlenk technique;

phenylacetylene; In acetonitrile; at 50 ℃; for 3h; Reagent/catalyst; Solvent; Temperature; regioselective reaction; Catalytic behavior; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.tetlet.2016.06.077

Reference yield: 94.0%

phenylacetylene (536-74-3) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane (143825-84-7) + 4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane (78782-27-1)

Guidance literature:

bis(pinacol)diborane; With C₂₇H₃₈ClCuN₂⁽¹⁺⁾*BF₄^(1-); sodium t-butanolate; In tetrahydrofuran; at 22 ℃; for 0.0833333h; Inert atmosphere;

phenylacetylene; In tetrahydrofuran; methanol; at 22 ℃; for 12h; Reagent/catalyst; Inert atmosphere;

DOI:10.1002/anie.202106107

Reference yield: 92.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane (78782-27-1)

Guidance literature:

With bis(cyclopentadienyl)dihydrozirconium; In toluene; at 25 ℃; for 0.166667h; under 760.051 Torr; Temperature; Inert atmosphere;

upstream raw materials:

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

phenylacetylene

styrene

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

Downstream raw materials:

2,2'‐(2‐phenylethane‐1,1‐diyl)bis(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane)

4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane

Refernces

• 1、 Vázquez-Gali?anes, Nuria,Fa?anás-Mastral, Martín. "Stereoselective Synthesis of Borylated 1,3-Dienes by Synergistic Cu/Pd Catalysis". . p. 4817 - 4820. Retrieved 2018.
• 2、 Bertrand, Guy,Engle, Keary M.,Gao, Yang,Grotjahn, Douglas B.,Jazzar, Rodolphe,Junor, Glen P.,Kang, Taeho,Kendrick, Aaron,Yazdani, Sima. "Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**". supporting information. p. 19871 - 19878. Retrieved 2021/08/13.
• 3、 Li, Tingting,Xu, Bo. "Mechanically Strong Heterogeneous Catalysts via Immobilization of Powderous Catalysts to Porous Plastic Tablets". supporting information. p. 2673 - 2678. Retrieved 2021/08/03.