2-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

Base Information

• Chemical Name: 2-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
• CAS No.: 950511-17-8
• Molecular Formula: C₂₂H₂₄B₂N₂O₂
• Molecular Weight: 370.067
• Hs Code.: 2934999090
• Mol file: 950511-17-8.mol

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

Chemical Property of 2-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

3-[3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,4-diaza-3-boratricyclo[7.3.1.0^{5,13}]trideca-1(13),5,7,9,11-pentaene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

There total 5 articles about 2-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 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: 88.0%

3-bromo-1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)benzene (927384-43-8) + bis(pinacol)diborane (73183-34-3) → 1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (950511-17-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; tricyclohexylphosphine; In 1,4-dioxane;

DOI:10.3390/molecules24030377

Reference yield:

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (1214264-88-6) → 1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (950511-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetra-(n-butyl)ammonium iodide; sodium acetate; dibenzoyl peroxide; tert.-butylnitrite / acetonitrile / 80 °C / Schlenk technique; Inert atmosphere

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine; potassium carbonate / 1,4-dioxane

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert.-butylnitrite; sodium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; tricyclohexylphosphine; dibenzoyl peroxide; In 1,4-dioxane; acetonitrile; 2: |Suzuki-Miyaura Coupling;

DOI:10.3390/molecules24030377

Reference yield:

m-Bromoaniline (591-19-5) → 1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (950511-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetra-(n-butyl)ammonium iodide; sodium acetate; dibenzoyl peroxide; tert.-butylnitrite / acetonitrile / 80 °C / Schlenk technique; Inert atmosphere

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine; potassium carbonate / 1,4-dioxane

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert.-butylnitrite; sodium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; tricyclohexylphosphine; dibenzoyl peroxide; In 1,4-dioxane; acetonitrile; 2: |Suzuki-Miyaura Coupling;

DOI:10.3390/molecules24030377

upstream raw materials:

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

bis(pinacol)diborane

naphthalene-1,8-diamine

(3-bromophenyl)boronic acid

Downstream raw materials:

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

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

(3-(7-ethyl-7H-imidazo[4,5-c]pyridazin-4-yl)benzene)boronic acid

7-ethyl-4-[4'-(methylsulfonyl)biphenyl-3-yl]-7H-imidazo[4,5-c]pyridazine