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

Base Information

• Chemical Name: (E)-2-(4-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 223919-54-8
• Molecular Formula: C14H18BClO2
• Molecular Weight: 264.56
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID00452262
• Nikkaji Number: J1.082.322F,J1.773.928J
• Mol file: 223919-54-8.mol

Synonyms:223919-54-8;(E)-2-(4-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;trans-2-(4-Chlorophenyl)vinylboronic acid pinacol ester;2-[(E)-2-(4-Chlorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-Chloro-trans-beta-styrylboronic acid pinacol ester;2-[2-(4-Chlorophenyl)vinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(4-Chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-chloro-beta-styrylboronic acid pinacol ester;1979181-68-4;2-((E)-2-(4-chlorophenyl)ethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(1E)-2-(4-Chlorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;DTXSID00452262;CQJXSSVRGHRVOK-MDZDMXLPSA-N;MFCD15144834;2-[2-(4-Chlorophenyl)vinyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;AKOS016006029;CS-W014056;GS-5614;H10137;A878552;EN300-26533265;Z2312382349;trans-2-(4-Chlorophenyl)vinylboronic acid pinacol ester, 97%;2-[(E)-4-Chlorostyryl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[(E)-2-(4-Chlorophenyl)vinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[2-(4-CHLOROPHENYL)ETHENYL]-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

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

Chemical Property:

• Melting Point: 88-92°C
• Boiling Point: 305.1±44.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.09±0.1 g/cm3(Predicted)
• LogP: 3.98460
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 264.1088377
• Heavy Atom Count: 18
• Complexity: 304

Purity/Quality:

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

trans-2-(4-Chlorophenyl)vinylboronic acid pinacol ester 97% ^*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)Cl
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/C2=CC=C(C=C2)Cl

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

There total 19 articles about (E)-2-(4-Chlorostyryl)-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: 99.0%

4-n-chlorophenylacetylene (873-73-4) + bis(pinacol)diborane (73183-34-3) → 2-[(E)-2-(4-chlorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (223919-54-8)

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: 99.0%

4-n-chlorophenylacetylene (873-73-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-[(E)-2-(4-chlorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (223919-54-8)

Guidance literature:

With (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride; tris-tert-butylphosphinimide, lithium salt; In benzene; at 20 ℃; for 13h; stereoselective reaction; Glovebox; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.03.011

Reference yield: 94.0%

4-vinylbenzyl chloride (1073-67-2,24991-47-7) + 2,3-dimethyl-2,3-butane diol (76-09-5) + 2-chloro-1,3,2-benzodioxaborole (55718-76-8) → 2-[(E)-2-(4-chlorophenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (223919-54-8)

Guidance literature:

4-vinylbenzyl chloride; 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:

4-vinylbenzyl chloride

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

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

(E)-4-chlorostyrylboronic acid

Downstream raw materials:

1-[(E)-2-bromoethenyl]-4-chlorobenzene

(Z)-1-bromo-2-(4-chlorophenyl)ethylene

(E)-1-chloro-4-(2-iodovinyl)benzene

(E)-2-[2-(4-chlorophenyl)ethenyl]benzaldehyde

Refernces

• 1、 Aelterman, Maude,Jubault, Philippe,Poisson, Thomas,Sayes, Morgane. "Electrochemical Hydroboration of Alkynes". supporting information. p. 8277 - 8282. Retrieved 2021/05/27.
• 2、 Gao, Ning,Hu, Tianding,Kang, Xiaomin,Lan, Xingwang,Wang, Zhenguang,Wu, Zhi-Lei,Zhao, Bin. "Highly efficient hydroboration of alkynes catalyzed by porous copper-organic framework under mild conditions". . p. 250 - 257. Retrieved 2021/10/25.