trans-2-(3-Fluorophenyl)vinylboronic acid

Base Information

• Chemical Name: trans-2-(3-Fluorophenyl)vinylboronic acid
• CAS No.: 849062-22-2
• Molecular Formula: C₈H₈BFO₂
• Molecular Weight: 165.96
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID201247887
• Mol file: 849062-22-2.mol

Synonyms:trans-2-(3-Fluorophenyl)vinylboronic acid;849062-22-2;(E)-(3-fluorostyryl)boronic acid;(3-Fluorostyryl)boronic acid;[(E)-2-(3-fluorophenyl)ethenyl]boronic acid;214907-19-4;[(1E)-2-(3-fluorophenyl)ethenyl]boronic acid;(E)-2-(3-Fluorophenyl)ethenylboronic acid;SCHEMBL387093;AMY1220;ONXKUGHKGCSZJO-SNAWJCMRSA-N;DTXSID201247887;MFCD06008297;AKOS015853014;(E)-2-(3-fluorophenyl)vinylboronic acid;BS-24184;(e)-2-(3-fluorphenyl)-vinyl boronic acid;CS-0175216;H12067;EN300-7379501;A863887;B-[(1E)-2-(3-Fluorophenyl)ethenyl]boronic acid

Chemical Property of trans-2-(3-Fluorophenyl)vinylboronic acid

Chemical Property:

• Vapor Pressure: 0.000205mmHg at 25°C
• Melting Point: 184-186 °C(lit.)
• Refractive Index: 1.565
• Boiling Point: 313.9°C at 760 mmHg
• PKA: 9.57±0.43(Predicted)
• Flash Point: 143.6°C
• PSA: 40.46000
• Density: 1.228g/cm³
• LogP: 0.85090
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.0601378
• Heavy Atom Count: 12
• Complexity: 161

Purity/Quality:

97% ^*data from raw suppliers

trans-2-(3-Fluorophenyl)vinylboronic acid ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C=CC1=CC(=CC=C1)F)(O)O
• Isomeric SMILES: B(/C=C/C1=CC(=CC=C1)F)(O)O
• Uses: Reactant for:Enantioselective diastereoselective synthesis of tetracyclins via metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation and Friedel-Crafts alkylationPalladium-catalyzed Suzuki-Miyaura coupling reactionsPreparation of anticonvulsant agentsPreparation of piperazinyl pyrimidylhydroxamic acid deriatives as histone deacetylase inhibitors and antitumor agentsPreparation of ethyl-substituted conjugated dienoates and dienones by stereoselective Suzuki cross-coupling

Technology Process of trans-2-(3-Fluorophenyl)vinylboronic acid

There total 1 articles about trans-2-(3-Fluorophenyl)vinylboronic 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-ethynyl-3-fluoro-benzene (2561-17-3) + benzo[1,3,2]dioxaborole (274-07-7) → (2-(3-fluorophenyl)ethenyl)boronic acid (214907-19-4,849062-22-2)

Guidance literature:

1-ethynyl-3-fluoro-benzene; benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 65 ℃; for 24h;

With water; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/acs.orglett.8b02234

Reference yield:

(E)-2-(3’-fluoro)phenylethenylboronic acid (849062-22-2) + 1,4-epoxy-1,4-dihydronaphthalene (573-57-9) → (1R,2R)-2-(3-fluorophenethyl)-1,2,3,4-tetrahydronaphthalen-1-ol

Guidance literature:

Multi-step reaction with 2 steps

1: chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; caesium carbonate / tetrahydrofuran; water / 16 h / 20 °C / Inert atmosphere

2: sodium acetate; toluene-4-sulfonic acid hydrazide / tetrahydrofuran; water / 20 h / Reflux

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; sodium acetate; caesium carbonate; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; water;

DOI:10.1021/jo201781x

upstream raw materials:

1-ethynyl-3-fluoro-benzene

benzo[1,3,2]dioxaborole