1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

Base Information

• Chemical Name: 1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
• CAS No.: 950511-16-7
• Molecular Formula: C₂₂H₂₄B₂N₂O₂
• Molecular Weight: 370.067
• Mol file: 950511-16-7.mol

Synonyms:1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

Chemical Property of 1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

There total 3 articles about 1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene 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: 82.0%

2-(4-chlorophenyl)-2,3-dihydro-1H-naphtho[1,8-de] [1,3,2]diazaborinine (1336918-65-0) + bis(pinacol)diborane (73183-34-3) → 1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (950511-16-7)

Guidance literature:

With tris(trimethylphosphine)nickel(II) chloride; (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; In tetrahydrofuran; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol202267t

Reference yield: 81.0%

2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de] [1,3,2]diazaborinine (927384-44-9) + bis(pinacol)diborane (73183-34-3) → 1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (950511-16-7)

Guidance literature:

With potassium acetate; [1,1'-bis(diphenylphospino)ferrocene]dichloropalladium; In dimethyl sulfoxide; at 80 ℃; for 17h;

DOI:10.1021/ol702420x

Reference yield:

4-Bromophenylboronic acid (5467-74-3) + naphthalene-1,8-diamine (479-27-6) → 1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (950511-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 3 h / Reflux

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 3 h / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; toluene;

DOI:10.3762/bjoc.10.297

upstream raw materials:

2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de] [1,3,2]diazaborinine

bis(pinacol)diborane

2-(4-chlorophenyl)-2,3-dihydro-1H-naphtho[1,8-de] [1,3,2]diazaborinine

4-Bromophenylboronic acid

Downstream raw materials:

4-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-(2-thiophenyl)benzene

4-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-(2-pyridyl)benzene

4-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4'-nitro-1,1'-biphenyl

2-([1,1'-biphenyl]-4-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine