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

Base Information

• Chemical Name: 3-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4'-methoxy-1,1'-biphenyl
• CAS No.: 1008097-01-5
• Molecular Formula: C₂₃H₁₉BN₂O
• Molecular Weight: 350.228
• Mol file: 1008097-01-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 3-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4'-methoxy-1,1'-biphenyl 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: 95.0%

1-bromo-4-methoxy-benzene (104-92-7) + 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) → 3-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4'-methoxy-1,1'-biphenyl (1008097-01-5)

Guidance literature:

With sodium hydroxide; bis(tri-tert-butylphosphine)palladium; In 1,4-dioxane; water; at 60 ℃; for 4h;

DOI:10.1021/ol702420x

Reference yield:

3-bromo-1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)benzene (927384-43-8) → 3-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4'-methoxy-1,1'-biphenyl (1008097-01-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / acetonitrile / 50 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; tricyclohexylphosphine; In 1,4-dioxane; acetonitrile; 1: |Suzuki-Miyaura Coupling / 2: |Suzuki-Miyaura Coupling;

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) → 3-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4'-methoxy-1,1'-biphenyl (1008097-01-5)

Guidance literature:

Multi-step reaction with 3 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

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / acetonitrile / 50 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; 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 / 3: |Suzuki-Miyaura Coupling;

DOI:10.3390/molecules24030377

upstream raw materials:

1-bromo-4-methoxy-benzene

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

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

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