N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Base Information

• Chemical Name: N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS No.: 267221-88-5
• Molecular Formula: C24H26BNO2
• Molecular Weight: 371.287
• Hs Code.: 2931900090
• European Community (EC) Number: 805-569-6
• DSSTox Substance ID: DTXSID40469874
• Nikkaji Number: J1.286.339J
• Wikidata: Q82297791
• Mol file: 267221-88-5.mol

Synonyms:267221-88-5;N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;4-(DIPHENYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER;4-(Diphenylamino)phenylboronic acid pinacol ester;MFCD13195770;4-(Diphenylamino)benzeneboronic acid pinacol ester;C24H26BNO2;Diphenyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]amine;YSZC357;SCHEMBL1702020;DTXSID40469874;VKSWIFGDKIEVFZ-UHFFFAOYSA-N;AMY30007;AKOS016339779;Diphenyl-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine;AS-2448;SY101872;CS-0130477;D5534;FT-0752058;F10493;4-(Diphenylamino)phenylboronic acid,pinacol ester;EN300-7375109;A877161;4-(Diphenylamino)phenylboronic acid pinacol ester, 95%;(4-(DIPHENYLAMINO)PHENYL)BORONIC ACID PINACOL ESTER;2-(4-Diphenylaminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(4-diphenylaminophenyl)-1,3,2-dioxaborolane;4-diphenylamino-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene;N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-phenylbenzenamine

Chemical Property of N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Chemical Property:

• Melting Point: 93-98 °C
• Boiling Point: 495.8±28.0 °C(Predicted)
• PKA: -3.32±0.60(Predicted)
• PSA: 21.70000
• Density: 1.12±0.1 g/cm3(Predicted)
• LogP: 5.45560
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 371.2056592
• Heavy Atom Count: 28
• Complexity: 469

Purity/Quality:

97% ^*data from raw suppliers

4-(Diphenylamino)phenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)N(C3=CC=CC=C3)C4=CC=CC=C4
• Uses: 4-(Diphenylamino)phenylboronic acid pinacol ester may be used to synthesize 4-(2,2′ -bithiophen-5-yl)- 5-phenylpyrimidine for potential usage in the development of sensing devices for the detection of nitroaromatic explosives. It can also be used in the synthesis of oligothiophene (electron donating group) for the fabrication of dye sensitized solar cells (DSSCs).

Technology Process of N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

There total 23 articles about N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 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: 97.0%

4-N,N-diphenylamino-1-bromobenzene (36809-26-4) + bis(pinacol)diborane (73183-34-3) → 4-(diphenylamino)phenylboronic pinacol ester (267221-88-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 24h; Inert atmosphere; Reflux;

DOI:10.1039/c8tc05259j

Reference yield: 96.0%

bis(pinacol)diborane (73183-34-3) → 4-(diphenylamino)phenylboronic pinacol ester (267221-88-5)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 80 ℃; for 30h; Inert atmosphere;

Reference yield: 91.6%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 4-N,N-diphenylamino-1-bromobenzene (36809-26-4) → 4-(diphenylamino)phenylboronic pinacol ester (267221-88-5)

Guidance literature:

4-N,N-diphenylamino-1-bromobenzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/j.tet.2010.09.087

upstream raw materials:

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-N,N-diphenylamino-1-bromobenzene

2,3-dimethyl-2,3-butane diol

4-(diphenylamino)phenyl boronic acid

Downstream raw materials:

4′?(N,N?diphenylamino)?[1,1′?biphenyl]?4?ol

7'-(4-(diphenylamino)phenyl)-9,9,9',9'-tetraoctyl-9H,9'H-2,2'-bifluorene-7-carbonitrile

7-(4-(N,N-diphenylamino)phenyl)-9,9-dioctyl-9H-fluorene-2-carbonitrile

5-(4-(diphenylamino)phenyl)-N-(5-(4-(diphenylamino)phenyl)thiazol-2-yl)-N-octylthiazol-2-amine