Benzenamine, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-N,N-diphenyl-

Base Information

• Chemical Name: Benzenamine, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-N,N-diphenyl-
• CAS No.: 408359-97-7
• Molecular Formula: C23H24BNO2
• Molecular Weight: 357.26
• DSSTox Substance ID: DTXSID90477883
• Nikkaji Number: J1.815.160J
• Wikidata: Q82310918
• Mol file: 408359-97-7.mol

Synonyms:408359-97-7;4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)-N,N-DIPHENYLANILINE;Benzenamine, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-N,N-diphenyl-;(4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl)diphenylamine;[4-(5,5-Dimethyl[1,3,2]dioxaborinan-2-yl)phenyl]diphenylamine;DTXSID90477883;SB83664

Chemical Property of Benzenamine, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-N,N-diphenyl-

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 357.1900092
• Heavy Atom Count: 27
• Complexity: 423

Purity/Quality:

99%,98%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OCC(CO1)(C)C)C2=CC=C(C=C2)N(C3=CC=CC=C3)C4=CC=CC=C4

Technology Process of Benzenamine, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-N,N-diphenyl-

There total 4 articles about Benzenamine, 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-N,N-diphenyl- 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: 93.0%

4-N,N-diphenylamino-1-bromobenzene (36809-26-4) + 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (201733-56-4) → [4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl]diphenylamine (408359-97-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 5.5h;

DOI:10.1039/b108408a

Reference yield: 89.0%

2,2-Dimethyl-1,3-propanediol (126-30-7) + 4-(diphenylamino)phenyl boronic acid (201802-67-7) → [4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl]diphenylamine (408359-97-7)

Guidance literature:

In toluene; Reflux;

DOI:10.1039/b911808j

Reference yield:

1,4-bromoiodobenzene (589-87-7) → [4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl]diphenylamine (408359-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / 1,10-phenanthroline; copper(I) chloride; potassium hydroxide / xylene; toluene / 48 h / Heating

2: 93 percent / potassium acetate; Pd(dppf)Cl₂ / dimethylsulfoxide / 5.5 h / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; 1,10-Phenanthroline; potassium acetate; copper(l) chloride; In dimethyl sulfoxide; toluene; xylene; 1: Ullman coupling;

DOI:10.1039/b108408a

upstream raw materials:

4-N,N-diphenylamino-1-bromobenzene

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

1,4-bromoiodobenzene

diphenylamine

Downstream raw materials:

(4-(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)-N,N-diphenyl-aniline)

3,6-bis-[(4'-diphenylamino)biphenyl-4-yl]-2,5-dioctylpyrrolo[3,4-c]pyrrole-1,4-dione

N-octyl-3,6-bis[4-(4-(diphenylamino)phenyl)phenyl]-1,4-diketo-pyrrolo[3,4-c]pyrrole

3,6-bis[4-(diphenylamino)phenyl]-9,10-phenanthrenequinone