4-(N,N-Dibenzylamino)phenylboronic acid

Base Information

• Chemical Name: 4-(N,N-Dibenzylamino)phenylboronic acid
• CAS No.: 159191-44-3
• Molecular Formula: C20H20 B N O2
• Molecular Weight: 317.195
• Hs Code.: 2931900090
• European Community (EC) Number: 681-465-2
• DSSTox Substance ID: DTXSID70597058
• Nikkaji Number: J3.472.333H
• Wikidata: Q82492527
• Mol file: 159191-44-3.mol

Synonyms:159191-44-3;4-(N,N-DIBENZYLAMINO)PHENYLBORONIC ACID;(4-(Dibenzylamino)phenyl)boronic acid;4-(DIBENZYLAMINO)PHENYLBORONIC ACID;[4-(Dibenzylamino)phenyl]boronic acid;4-(Dibenzylamino)benzene boronic acid;4-(N,N-Dibenzylamino)phenylboronicacid;SCHEMBL2320409;DTXSID70597058;KLGQJKOCSXZOBV-UHFFFAOYSA-N;(4-(Dibenzylamino)phenyl)boronicacid;MFCD06798225;AKOS015839276;AB29841;AM86664;BS-2017;DB-010632;CS-0175260;[4-[Bis(phenylmethyl)amino]phenyl]boronic acid;A883317;4-(Dibenzylamino)benzeneboronic acid

Chemical Property of 4-(N,N-Dibenzylamino)phenylboronic acid

Chemical Property:

• Vapor Pressure: 9.09E-13mmHg at 25°C
• Melting Point: 184-188°C
• Refractive Index: 1.641
• Boiling Point: 546.3°Cat760mmHg
• Flash Point: 284.2°C
• PSA: 43.70000
• Density: 1.19g/cm³
• LogP: 2.57320
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 317.1587090
• Heavy Atom Count: 24
• Complexity: 326

Purity/Quality:

97% ^*data from raw suppliers

4-(N,N-Dibenzylamino)phenylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)N(CC2=CC=CC=C2)CC3=CC=CC=C3)(O)O

Technology Process of 4-(N,N-Dibenzylamino)phenylboronic acid

There total 3 articles about 4-(N,N-Dibenzylamino)phenylboronic 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: 42.0%

N,N-dibenzyl-4-bromoaniline (65145-14-4) → [4-(dibenzylamino)phenyl]boronic acid (159191-44-3)

Guidance literature:

N,N-dibenzyl-4-bromoaniline; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere; Schlenk technique; Reflux; Enzymatic reaction;

With tetrahydrofuran; Triisopropyl borate; In hexane; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.5b13190

Reference yield:

Triisopropyl borate (5419-55-6) + N,N-dibenzyl-4-bromoaniline (65145-14-4) → [4-(dibenzylamino)phenyl]boronic acid (159191-44-3)

Guidance literature:

N,N-dibenzyl-4-bromoaniline; With n-butyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 3.25h;

With hydrogenchloride; water; In tetrahydrofuran; diethyl ether; at 20 ℃; for 0.333333h;

Reference yield:

4-bromo-aniline (106-40-1) → [4-(dibenzylamino)phenyl]boronic acid (159191-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium carbonate / N,N-dimethyl-formamide / 110 °C / Inert atmosphere; Schlenk technique

2.1: n-butyllithium / hexane; tetrahydrofuran / -78 °C / Inert atmosphere; Schlenk technique; Reflux; Enzymatic reaction

2.2: Inert atmosphere; Schlenk technique

With n-butyllithium; sodium carbonate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jacs.5b13190

upstream raw materials:

Triisopropyl borate

N,N-dibenzyl-4-bromoaniline

4-bromo-aniline

Downstream raw materials:

2-{1-[4-(dibenzylamino)phenyl]cyclobutyl}-N,N-dimethylacetamide

{1-[4-(dibenzylamino)phenyl]cyclobutyl}acetic acid

N,N-dibenzyl-4-[1-(2-fluoroethyl)cyclobutyl]aniline

2-{1-[4-(dibenzylamino)phenyl]cyclobutyl}ethanol