2-Vinylphenylboronic acid

Base Information

• Chemical Name: 2-Vinylphenylboronic acid
• CAS No.: 15016-42-9
• Molecular Formula: C8H9BO2
• Molecular Weight: 147.969
• Hs Code.: 2931900090
• European Community (EC) Number: 929-220-3,681-433-8
• DSSTox Substance ID: DTXSID80378577
• Nikkaji Number: J1.634.713B
• Wikidata: Q82168057
• Mol file: 15016-42-9.mol

Synonyms:2-Vinylphenylboronic acid;15016-42-9;2-Vinylbenzeneboronic acid;(2-ethenylphenyl)boronic Acid;(2-vinylphenyl)boronic acid;Boronic acid, (ethenylphenyl)-;MFCD01074659;2-Vinylphenylboronicacid;STYRENE-2-BORONIC ACID;2-vinyl-phenylboronic acid;2-vinyl benzene boronic acid;(2-vinylphenyl) boronic acid;SCHEMBL393924;DTXSID80378577;QHFAXRHEKNHTDH-UHFFFAOYSA-N;Boronic acid, B-(2-ethenylphenyl)-;2-Vinylphenylboronic acid, AldrichCPR;AKOS004116554;AB08106;CS-W016344;PS-9573;B-(2-ETHENYLPHENYL)BORONIC ACID;SY025003;FT-0613470;V0140;F20516;J-510362;2-Vinylphenylboronic Acid (contains varying amounts of Anhydride)

Chemical Property of 2-Vinylphenylboronic acid

Chemical Property:

• Vapor Pressure: 0.000208mmHg at 25°C
• Melting Point: 105-107°C
• Refractive Index: 1.539
• Boiling Point: 313.7 °C at 760 mmHg
• PKA: 8.53±0.58(Predicted)
• Flash Point: 143.5 °C
• PSA: 40.46000
• Density: 1.09 g/cm³
• LogP: 0.00940
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: Insoluble 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: 136

Purity/Quality:

99% ^*data from raw suppliers

2-VinylphenylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-41
• Safety Statements: 26-36-37/39-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1C=C)(O)O
• Uses: suzuki reaction 2-Vinylbenzeneboronic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields. It is also used in Suzuki reaction.

Technology Process of 2-Vinylphenylboronic acid

There total 9 articles about 2-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: 80.0%

Triisopropyl borate (5419-55-6) + 2-bromostyrene (2039-88-5) → 2-vinylbenzeneboronic acid (15016-42-9)

Guidance literature:

2-bromostyrene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; at 20 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In water; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00879

Reference yield: 74.0%

boric acid tributyl ester (688-74-4) + 2-bromostyrene (2039-88-5) → 2-vinylbenzeneboronic acid (15016-42-9)

Guidance literature:

With water; magnesium; In tetrahydrofuran; diethyl ether; byproducts: C4H9OH; preparation of Grignard-compound in THF, addn. of soln. to excess B(OC4H9)3 in ether at -70°C, warming to room temp., hydrolysis mit 3n HCl, extractn. with ether, removal of ether, addn. of H2O, removal of C4H9OH;;

DOI:10.1021/jo01054a071

Reference yield: 35.0%

Trimethyl borate (121-43-7,63156-11-6) + 2-bromostyrene (2039-88-5) + water (7732-18-5) → 2-vinylbenzeneboronic acid (15016-42-9)

Guidance literature:

2-bromostyrene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h; Schlenk technique;

Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 10h; Schlenk technique;

water; With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 1h; pH=6 - 7; Schlenk technique;

DOI:10.1021/acs.orglett.8b02247

upstream raw materials:

{(C₆H₄-2-CHBrCH₃)O}3

4,4,5,5-tetramethyl-2-(2-vinylphenyl)-1,3,2-dioxaborolane

boric acid tributyl ester

2-bromostyrene

Downstream raw materials:

1-phenyl-1H-indole

Refernces

• 1、 Xu, Shiyang,Huang, Baoliang,Qiao, Guanyu,Huang, Ziyue,Zhang, Zhen,Li, Zongyang,Wang, Peng,Zhang, Zhenhua. "Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide". supporting information. p. 5578 - 5582. Retrieved 2018/09/25.
• 2、 Benhamou, Laure,Walker, Daniel W.,Bu?ar, Dejan-Kre?imir,Aliev, Abil E.,Sheppard, Tom D.. "Synthesis of substituted benzooxaborinin-1-ols via palladium-catalysed cyclisation of alkenyl- and alkynyl-boronic acids". supporting information. p. 8039 - 8043. Retrieved 2016/09/09.