(E)-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile

Base Information

• Chemical Name: (E)-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile
• CAS No.: 172512-93-5
• Molecular Formula: C15H20BNO3
• Molecular Weight: 255.124
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID40455510
• Nikkaji Number: J2.600.773I
• Wikidata: Q82277561
• Mol file: 172512-93-5.mol

Synonyms:172512-93-5;(E)-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile;4-Cyano-trans-beta-styrylboronic acid pinacol ester;4-[(E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]benzonitrile;DTXSID40455510;PTVXZOZMWVSOOR-MDZDMXLPSA-N;AMY37307;BCP15850;CS-B1124;XGA51293;MFCD19703873;AKOS016006008;DS-14546;(E)-4-Cyano-styrylboronic acid pinacol ester;C73312;EN300-802098;EN300-7361548;4-Cyano-trans-beta-styrylboronic acidpinacol ester;A881868;Z2312384934;2-[(E)-4-Cyanostyryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-[2-(tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]benzonitrile;4-[(E)-2-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ETHENYL]BENZONITRILE

Chemical Property of (E)-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile

Chemical Property:

• Boiling Point: 338.5±52.0 °C(Predicted)
• PSA: 42.25000
• Density: 1.05±0.1 g/cm3(Predicted)
• LogP: 3.20288
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 255.1430590
• Heavy Atom Count: 19
• Complexity: 384

Purity/Quality:

97% ^*data from raw suppliers

4-Cyano-trans-beta-styrylboronic acidpinacol ester 95+% ^*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)C=CC2=CC=C(C=C2)C#N
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/C2=CC=C(C=C2)C#N

Technology Process of (E)-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile

There total 4 articles about (E)-4-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile 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: 90.0%

4-cyanophenylacetylene (3032-92-6) + bis(pinacol)diborane (73183-34-3) → (E)-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile (172512-93-5)

Guidance literature:

With 2.9 weight% Cu(II) loaded porous coordination network-222 nanoparticles; In ethanol; water; at 80 ℃; regioselective reaction; Sealed tube;

DOI:10.1016/j.jcat.2021.06.013

Reference yield: 86.0%

4-cyanophenylacetylene (3032-92-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (E)-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile (172512-93-5)

Guidance literature:

With sodium triethylborohydride; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; toluene; at 100 ℃; for 24h; regioselective reaction; Microwave irradiation; Inert atmosphere;

DOI:10.1039/c8cc08361d

Reference yield:

4-cyanophenylacetylene (3032-92-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1-p-cyanophenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene (1038849-82-9) + 4-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)benzonitrile + (E)-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzonitrile (172512-93-5)

Guidance literature:

With ^PhboxmiCo(CH₂SiMe₃); In hexane; toluene; at 20 ℃; for 15h; regioselective reaction;

DOI:10.1002/anie.202009625

upstream raw materials:

4-cyanophenylacetylene

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

bis(pinacol)diborane

4-ethenylbenzonitrile

Downstream raw materials:

(E)-4-(3,3,3-trifluoroprop-1-enyl)benzenecarbonitrile