4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde

Base Information

• Chemical Name: 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde
• CAS No.: 1040424-52-9
• Molecular Formula: C19H21BO3
• Molecular Weight: 308.17924
• Hs Code.: 2931900090
• Mol file: 1040424-52-9.mol

Synonyms:4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde;4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzaldehyde

Chemical Property of 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde

Chemical Property:

• Melting Point: 140.4-141.4 °C
• Boiling Point: 446.8±38.0 °C(Predicted)
• PSA: 35.53000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 3.46530

Purity/Quality:

97% ^*data from raw suppliers

4''-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1''-biphenyl]-4-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde

There total 3 articles about 4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde 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: 95.3%

4-formyl-4'-bromobiphenyl (50670-58-1) + bis(pinacol)diborane (73183-34-3) → 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde (1040424-52-9)

Guidance literature:

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 72h; Inert atmosphere;

DOI:10.1021/jacs.9b08017

Reference yield:

1,4-bromoiodobenzene (589-87-7) → 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde (1040424-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 80 °C / Inert atmosphere; Schlenk technique

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere; Schlenk technique

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; potassium carbonate; In 1,4-dioxane; water; dimethyl sulfoxide; 1: |Suzuki Coupling;

DOI:10.1039/d1tc05065f

Reference yield:

4-formylphenylboronic acid, (87199-17-5) → 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-carbaldehyde (1040424-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 80 °C / Inert atmosphere; Schlenk technique

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere; Schlenk technique

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; potassium carbonate; In 1,4-dioxane; water; dimethyl sulfoxide; 1: |Suzuki Coupling;

DOI:10.1039/d1tc05065f

upstream raw materials:

4-formyl-4'-bromobiphenyl

bis(pinacol)diborane

1,4-bromoiodobenzene

4-formylphenylboronic acid,

Downstream raw materials:

C₈₄H₈₆O₆