1-Phenylvinylboronic acid

Base Information

• Chemical Name: 1-Phenylvinylboronic acid
• CAS No.: 14900-39-1
• Molecular Formula: C8H9BO2
• Molecular Weight: 147.969
• Hs Code.: 2931900090
• European Community (EC) Number: 807-828-9
• DSSTox Substance ID: DTXSID50407429
• Nikkaji Number: J1.678.616K
• Wikidata: Q72499187
• Mol file: 14900-39-1.mol

Synonyms:1-Phenylvinylboronic acid;14900-39-1;(1-Phenylvinyl)boronic acid;1-phenylethenylboronic Acid;alpha-Phenyl vinylboronic acid;(1-Phenylvinyl)boronicacid;MFCD01074578;(1-PHENYLETHENYL)BORONIC ACID;SCHEMBL101826;1-Phenylvinylboronic acid, 95%;DTXSID50407429;STYRENE ALPHA-BORONIC ACID;YJCPVMYUISTDKG-UHFFFAOYSA-N;AMY24763;AKOS015840592;AB08051;PS-9504;SY024635;CS-0109518;FT-0636257;FT-0651827;EN300-212506;S12165;ALPHA-METHYLENE-ALPHA-TOLUENEBORONIC ACID;A808832;J-008540

Chemical Property of 1-Phenylvinylboronic acid

Chemical Property:

• Vapor Pressure: 0.000126mmHg at 25°C
• Melting Point: 125 °C (dec.)(lit.)
• Refractive Index: 1.536
• Boiling Point: 321.092 °C at 760 mmHg
• PKA: 8.98±0.43(Predicted)
• Flash Point: 147.991 °C
• PSA: 40.46000
• Density: 1.09 g/cm³
• LogP: 0.71180
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 148.0695597
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

99% ^*data from raw suppliers

1-Phenylvinylboronic acid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

Useful:

• Canonical SMILES: B(C(=C)C1=CC=CC=C1)(O)O
• Uses: Reactant involved in:Halogenation of alkynes for preparation of enol estersLiebeskind-Srogl cross-couplingHomocoupling of arylboronic acids for synthesis of biarylsIterative cross-coupling of boronate building blocksEnantioselective hydrogenation of hydroxyphenyl styrenesSamarium diiodide-mediated cyclization for synthesis of substituted benzannulated cyclooctanol derivativesSuzuki-Miyaura cross-coupling for synthesis of C-6-substituted uridine phosphonates

Technology Process of 1-Phenylvinylboronic acid

There total 10 articles about 1-Phenylvinylboronic 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:

(1,2-dibromoethyl)benzene (102921-26-6,93-52-7) → phenylvinylboronic acid (14900-39-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / methanol; tetrahydrofuran / 3 h / 20 °C

2.1: tert.-butyl lithium / diethyl ether; hexane / 0.5 h / -78 °C

2.2: -78 °C

3.1: hydrogenchloride / water / 2 h / 20 °C

With hydrogenchloride; tert.-butyl lithium; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; water;

DOI:10.1021/ja506579t

Reference yield:

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → phenylvinylboronic acid (14900-39-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid; lithium bromide; sodium periodate / 20 °C

2.1: potassium carbonate / methanol; tetrahydrofuran / 3 h / 20 °C

3.1: tert.-butyl lithium / diethyl ether; hexane / 0.5 h / -78 °C

3.2: -78 °C

4.1: hydrogenchloride / water / 2 h / 20 °C

With hydrogenchloride; sodium periodate; tert.-butyl lithium; potassium carbonate; acetic acid; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; water;

DOI:10.1021/ja506579t

Reference yield:

dihydroxy-methyl-borane (13061-96-6) + 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane (143825-84-7) → phenylvinylboronic acid (14900-39-1)

Guidance literature:

With hydrogenchloride; In water; acetone; at 20 ℃;

DOI:10.1021/acs.orglett.9b00584

upstream raw materials:

Trimethyl borate

1-bromovinylbenzene

(1,2-dibromoethyl)benzene

styrene

Downstream raw materials:

1-(4-cyanophenyl)-1-phenylethylene

1-(2-cyanophenyl)-1-phenylethylene

1-[(2-hydroxy-5-methyl)phenyl]-1-phenylethylene

(S)-4-methyl-2-(1-phenylethyl)phenol

Refernces

• 1、 Phipps, Erik J. T.,Rovis, Tomislav. "Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols". . . Retrieved 2019/05/06.
• 2、 Phipps, Erik J. T.,Piou, Tiffany,Rovis, Tomislav. "Rhodium(III)-Catalyzed Cyclopropanation of Unactivated Olefins Initiated by C-H Activation". . p. 1787 - 1790. Retrieved 2019/09/09.