4-Vinylphenylboronic acid

Base Information

• Chemical Name: 4-Vinylphenylboronic acid
• CAS No.: 2156-04-9
• Molecular Formula: C8H9BO2
• Molecular Weight: 147.969
• Hs Code.: 29163990
• European Community (EC) Number: 629-120-7
• DSSTox Substance ID: DTXSID10370281
• Nikkaji Number: J687.906C
• Wikidata: Q72471222
• Mol file: 2156-04-9.mol

Synonyms:4-vinylphenyl boronic acid;VPBA cpd

Chemical Property of 4-Vinylphenylboronic acid

Chemical Property:

• Appearance/Colour: White light beige crystalline powder
• Vapor Pressure: 0.000341mmHg at 25°C
• Melting Point: 190-193 °C
• Refractive Index: 1.539
• Boiling Point: 306.255 °C at 760 mmHg
• PKA: 8.62±0.17(Predicted)
• Flash Point: 139 °C
• PSA: 40.46000
• Density: 1.096 g/cm³
• LogP: 0.00940
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility.: Soluble in ethanol, dimethylsulfoxide, tetrahydrofuran and diethyl ether. Slightly soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 148.0695597
• Heavy Atom Count: 11
• Complexity: 128

Purity/Quality:

99% ^*data from raw suppliers

4-Vinylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C=C)(O)O
• Uses: suzuki reaction 4-Vinylphenylboronic acid is commonly used in the synthesis of styrene-based organoboron polymers such as vinyl-oligo(fluorene) polymer and boronic ester based self-healing polymer. It can also be used as a precursor in the synthesis of aggregation induced emission (AIE) dye.

Technology Process of 4-Vinylphenylboronic acid

There total 11 articles about 4-Vinylphenylboronic acid 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: 97.0%

4-vinylbenzyl chloride (1073-67-2,24991-47-7) → 4-Vinylphenylboronic acid (2156-04-9,593231-72-2)

Guidance literature:

4-vinylbenzyl chloride; With magnesium; In tetrahydrofuran;

With Trimethyl borate; In tetrahydrofuran; at -45 - 20 ℃; for 3h;

With hydrogenchloride; In tetrahydrofuran; water;

DOI:10.1021/om200193r

Reference yield: 91.0%

(4-(1,2-dibromoethyl)phenyl)boronic acid (42728-38-1) → 4-Vinylphenylboronic acid (2156-04-9,593231-72-2)

Guidance literature:

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; sodium carbonate; In dimethyl sulfoxide; at 20 ℃; for 1.5h; Inert atmosphere; Irradiation;

DOI:10.1002/chem.201601819

Reference yield: 52.0%

4-vinylbenzyl chloride (1073-67-2,24991-47-7) + Trimethyl borate (121-43-7,63156-11-6) → 4-Vinylphenylboronic acid (2156-04-9,593231-72-2)

Guidance literature:

4-vinylbenzyl chloride; With magnesium; In tetrahydrofuran;

Trimethyl borate; In tetrahydrofuran; at -45 - 20 ℃; for 3h;

DOI:10.1007/s11224-016-0879-6

upstream raw materials:

{B(C₆H₄-4-CHBrCH₃)O}3

(4-Vinylphenyl)magnesium chloride

Trimethyl borate

boric acid tributyl ester

Downstream raw materials:

O,O'-(4-vinyl-phenylboranediyl)-L_g-tartaric acid diethyl ester

diethoxy-(4-vinyl-phenyl)-borane

(R)-2-(4-vinyl-phenyl)-[1,3,2]dioxaborolane-4-carboxylic acid octyl ester

(R)-2-(4-vinyl-phenyl)-[1,3,2]dioxaborolane-4-carboxylic acid 4-nitro-benzyl ester

Refernces

• 1、 Park, Eun Joo,Bae, Chulsung. "Superacidic porous polymer catalyst and its application in esterification of carboxylic acid". . p. 493 - 500. Retrieved 2017/02/23.
• 2、 Cash, Jessica J.,Kubo, Tomohiro,Bapat, Abhijeet P.,Sumerlin, Brent S.. "Room-temperature self-healing polymers based on dynamic-covalent boronic esters". . p. 2098 - 2106. Retrieved 2015/04/27.