1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)phenyl]ethanone

Base Information

• Chemical Name: 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)phenyl]ethanone
• CAS No.: 866141-77-7
• Molecular Formula: C₁₅H₁₈BF₃O₃
• Molecular Weight: 314.112
• DSSTox Substance ID: DTXSID201127481
• Mol file: 866141-77-7.mol

Synonyms:866141-77-7;Ethanone, 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)phenyl]-;1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)phenyl]ethanone;DTXSID201127481

Chemical Property of 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)phenyl]ethanone

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 314.1301091
• Heavy Atom Count: 22
• Complexity: 432

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=C(C=C2)C(=O)C)C(F)(F)F

Technology Process of 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)phenyl]ethanone

There total 1 articles about 1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)phenyl]ethanone 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-(4-chloro-3-(trifluoromethyl)phenyl)ethanone (129825-11-2) + bis(pinacol)diborane (73183-34-3) → 2-trifluoromethyl-4-acetylphenylboronic acid pinacol ester (866141-77-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In toluene; for 48h; Heating;

DOI:10.1021/jm049085v

Reference yield:

2-trifluoromethyl-4-acetylphenylboronic acid pinacol ester (866141-77-7) → 6-cyclopropylmethyl-7-ethyl-2-(4-isopropyl-2-trifluoromethyl-phenyl)-4-methyl-7,8-dihydro-6H-1,3,6,8a-tetraaza-acenaphthylene

Guidance literature:

Multi-step reaction with 4 steps

1: 3.78 g / aq. sodium carbonate; barium hydroxide; Pd(PPh₃)4 / toluene; ethanol / 100 °C

2: tetrahydrofuran; toluene / 2.5 h / 20 - 60 °C

3: 45 percent / MgSO₄; p-toluenesulfonic acid; trifluoroacetic acid / toluene / 16 h / Heating

4: H₂ / PtO / ethanol / 1 h / 2068.59 Torr

With barium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; sodium carbonate; magnesium sulfate; toluene-4-sulfonic acid; trifluoroacetic acid; platinum(II) oxide; In tetrahydrofuran; ethanol; toluene; 1: Suzuki coupling;

DOI:10.1021/jm049085v

Reference yield:

2-trifluoromethyl-4-acetylphenylboronic acid pinacol ester (866141-77-7) + (S)-6-cyclopropylmethyl-2-bromo-7-ethyl-4-methyl-7,8-dihydro-6H-1,3,6,8a-tetraazaacenaphthylene (866141-75-5) → 1-[4-(6-cyclopropylmethyl-7-ethyl-4-methyl-7,8-dihydro-6H-1,3,6,8a-tetraaza-acenaphthylen-2-yl)-3-trifluoromethyl-phenyl]-ethanone (866141-78-8)

Guidance literature:

With barium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; toluene; at 100 ℃;

DOI:10.1021/jm049085v

upstream raw materials:

1-(4-chloro-3-(trifluoromethyl)phenyl)ethanone

bis(pinacol)diborane

Downstream raw materials:

1-[4-(6-cyclopropylmethyl-7-ethyl-4-methyl-7,8-dihydro-6H-1,3,6,8a-tetraaza-acenaphthylen-2-yl)-3-trifluoromethyl-phenyl]-ethanone

6-cyclopropylmethyl-7-ethyl-2-(4-isopropenyl-2-trifluoromethyl-phenyl)-4-methyl-7,8-dihydro-6H-1,3,6,8a-tetraaza-acenaphthylene