(E)-2-(3-Methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: (E)-2-(3-Methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 871125-68-7
• Molecular Formula: C15H21 B O3
• Molecular Weight: 260.141
• Hs Code.: 2931900090
• European Community (EC) Number: 624-838-7
• DSSTox Substance ID: DTXSID101143171
• Nikkaji Number: J2.251.842I,J3.372.945F
• Mol file: 871125-68-7.mol

Synonyms:871125-68-7;(E)-2-(3-Methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;trans-2-(3-Methoxyphenyl)vinylboronic acid pinacol ester;2-[(E)-2-(3-METHOXYPHENYL)ETHENYL]-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-(2-(3-Methoxyphenyl)ethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[2-(3-METHOXYPHENYL)ETHENYL]-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;SCHEMBL3581509;MYKJZXRWDIWMDR-MDZDMXLPSA-N;DTXSID101143171;WJB12568;MFCD07784374;AKOS015893186;GS-6629;CS-0254197;EN300-802075;H10110;EN300-7356383;A862848;Z2315585614;2-(3-Methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;trans-2-(3-Methoxyphenyl)vinylboronic acid pinacol ester, 96%;2-[(1E)-2-(3-Methoxyphenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(E)-2-(3-Methoxy-phenyl)-vinyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2132383-00-5

Chemical Property of (E)-2-(3-Methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.000908mmHg at 25°C
• Melting Point: 36-42 °C(lit.)
• Refractive Index: 1.503
• Boiling Point: 313.5°C at 760 mmHg
• Flash Point: 110 °C
• Density: 1.02g/cm³
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 260.1583747
• Heavy Atom Count: 19
• Complexity: 322

Purity/Quality:

97% ^*data from raw suppliers

trans-2-(3-Methoxyphenyl)vinylboronic acid pinacol ester 96% ^*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(=CC=C2)OC
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/C2=CC(=CC=C2)OC

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

There total 7 articles about (E)-2-(3-Methoxystyryl)-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: 89.0%

1-ethynyl-3-methoxybenzene (768-70-7) + bis(pinacol)diborane (73183-34-3) → (E)-2-(3-methoxystyryl)-4,4,5,5-tetramethyl-1,3-dioxa-2-borolane (871125-68-7)

Guidance literature:

With [Cu(phen)(xantphosTEPD)]PF₆; potassium carbonate; In water; acetonitrile; at 20 ℃; for 7h; diastereoselective reaction; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1002/anie.202101874

Reference yield: 87.0%

1-ethynyl-3-methoxybenzene (768-70-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → (E)-2-(3-methoxystyryl)-4,4,5,5-tetramethyl-1,3-dioxa-2-borolane (871125-68-7)

Guidance literature:

With trimethylsilylmethyllithium; In neat (no solvent); at 90 ℃; for 8h; Schlenk technique; Glovebox; Inert atmosphere;

DOI:10.1002/ejic.202100895

Reference yield: 84.0%

3-methoxystyrene (626-20-0) + 2,3-dimethyl-2,3-butane diol (76-09-5) + 2-chloro-1,3,2-benzodioxaborole (55718-76-8) → (E)-2-(3-methoxystyryl)-4,4,5,5-tetramethyl-1,3-dioxa-2-borolane (871125-68-7)

Guidance literature:

3-methoxystyrene; 2-chloro-1,3,2-benzodioxaborole; With N-Methyldicyclohexylamine; (bis(3,5-di-tertbutylphenyl)(tert-butyl)phosphine)₂PdCl₂; lithium iodide; at 70 ℃; for 24h; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; at 20 ℃; for 1h;

DOI:10.1021/jacs.6b02914

upstream raw materials:

1-ethynyl-3-methoxybenzene

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

bis(pinacol)diborane

3-methoxystyrene

Downstream raw materials:

(E)-1-(2-iodovinyl)-3-methoxylbenzene

trans-2-(3-methoxyphenyl)vinylboronic acid

5-[(E)-2-(3-methoxyphenyl)vinyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile

2-[(E)-2-(4-methoxyphenyl)vinyl]-9,10-dihydro-8H-3,8,10-triaza-pentaleno[2,1-a]naphthalen-7-one