(4-(Bis(4-methoxyphenyl)amino)phenyl)boronic acid

Base Information

• Chemical Name: (4-(Bis(4-methoxyphenyl)amino)phenyl)boronic acid
• CAS No.: 201802-29-1
• Molecular Formula: C20H20BNO4
• Molecular Weight: 349.194
• European Community (EC) Number: 835-530-9
• Nikkaji Number: J2.254.028I
• Mol file: 201802-29-1.mol

Synonyms:201802-29-1;(4-(Bis(4-methoxyphenyl)amino)phenyl)boronic acid;Boronic acid, B-[4-[bis(4-methoxyphenyl)amino]phenyl]-;[4-(4-methoxy-N-(4-methoxyphenyl)anilino)phenyl]boronic acid;[4-[bis(4-methoxyphenyl)amino]phenyl]boronic Acid;[4-[Bis(4-methoxyphenyl)amino]phenyl]boronic Acid (contains varying amounts of Anhydride);4-(bis(4-methoxyphenyl)amino)phenylboronic acid;4-[Bis(4-methoxyphenyl)amino]phenylboronic acid;Boronic acid, [4-[bis(4-methoxyphenyl)amino]phenyl]-;YSCH0208;BIA80229;MFCD28385171;SB83286;BS-52192;B6005;CS-0112816;T70529;(4-(Bis(4-methoxyphenyl)amino)phenyl)boronicacid;A900815;oronicacid,B-[4-[bis(4-methoxyphenyl)amino]phenyl]-;boronic acid,b-(4-(bis(4-methoxyphenyl)amino)phenyl)-

Chemical Property of (4-(Bis(4-methoxyphenyl)amino)phenyl)boronic acid

Chemical Property:

• Boiling Point: 559.8±60.0 °C(Predicted)
• PKA: 8?+-.0.16(Predicted)
• PSA: 62.16000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 2.85340
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 349.1485383
• Heavy Atom Count: 26
• Complexity: 377

Purity/Quality:

99%, ^*data from raw suppliers

[4-[Bis(4-methoxyphenyl)amino]phenyl]boronic Acid (contains varying amounts of Anhydride) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)N(C2=CC=C(C=C2)OC)C3=CC=C(C=C3)OC)(O)O

Technology Process of (4-(Bis(4-methoxyphenyl)amino)phenyl)boronic acid

There total 12 articles about (4-(Bis(4-methoxyphenyl)amino)phenyl)boronic acid 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%

N,N-bis(4-methoxyphenyl)-4'-iodophenylamine (201802-15-5) → N,N'-bis(4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (201802-29-1)

Guidance literature:

N,N-bis(4-methoxyphenyl)-4'-iodophenylamine; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

With Trimethyl borate; In tetrahydrofuran;

DOI:10.1021/jo051183g

Reference yield: 65.0%

4-bromo-N,N-bis-(4-methoxyphenyl)aniline (194416-45-0) → N,N'-bis(4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (201802-29-1)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; bis(pinacol)diborane; In N,N-dimethyl-formamide; at 80 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1002/ejoc.201201629

Reference yield: 41.0%

Trimethyl borate (121-43-7,63156-11-6) + N,N-bis(4-methoxyphenyl)-4'-iodophenylamine (201802-15-5) → N,N'-bis(4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (201802-29-1)

Guidance literature:

N,N-bis(4-methoxyphenyl)-4'-iodophenylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -80 - -60 ℃; for 2h;

Trimethyl borate; In tetrahydrofuran; hexane; at -80 - 20 ℃;

DOI:10.1021/acs.orglett.1c01861

upstream raw materials:

N,N-bis(4-methoxyphenyl)-4'-iodophenylamine

para-iodoanisole

N,N-bis(4-methoxyphenyl)aniline

aniline

Downstream raw materials:

C₄₈H₄₉N₃O₆

5-(3-(4-(bis(4-methoxyphenyl)amino)phenyl)-10-octyl-10H-phenothiazin-7-yl)thiophene-2-carbaldehyde

3-[4-[4-(N,N-bis(4-methoxyphenyl)amino)phenyl]phenyl]-6-(4-bromophenyl)-2,5-di-n-butyl-pyrrolo[3,4-c]pyrrole-1,4-dione

5-(13-(5-(4-(bis(4-methoxyphenyl)amino)phenyl)-4-hexylthiophen-2-yl)-11,12-bis(hexyloxy)dibenzo[a,c]phenazin-10-yl)-3-hexylthiophene-2-carbaldehyde

Refernces

Aggregation-induced emission and large two-photon absorption cross-sections of diketopyrrolopyrrole (DPP) derivatives

10.1071/CH11410

The research focuses on the design and synthesis of a new series of triphenylamine-based diketopyrrolo-pyrrole (DPP) compounds, DPP-I, DPP-II, and DPP-III, which exhibit aggregation-induced emission (AIE) and large two-photon absorption cross-sections. The study investigates their one- and two-photon absorption properties, revealing that these compounds are weakly fluorescent in THF solution but show significantly enhanced red fluorescence in water/THF mixtures due to restricted intramolecular vibration and rotation in nano-aggregates. The two-photon absorption (2PA) cross-sections were measured using the open aperture Z-scan technique, yielding values of 188, 275, and 447 GM for DPP-I, DPP-II, and DPP-III, respectively. The research utilized various reactants such as 3,6-bis-(4-bromophenyl)-2,5-di-n-butyl-pyrrolo[3,4-c]pyrrole-1,4-dione (compound 1), 4-(bis(4-methoxyphenyl)-amino)phenyl boronic acid (compound 2), and palladium catalysts for the synthesis of the DPP derivatives. The compounds were characterized using 1H NMR, 13C NMR spectrometry, and HRMS, while their optical properties were analyzed through UV-vis absorption and fluorescence spectroscopy, providing a comprehensive understanding of their potential as biophotonic materials.

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