4-Aminophenylboronic acid pinacol ester

Base Information

• Chemical Name: 4-Aminophenylboronic acid pinacol ester
• CAS No.: 214360-73-3
• Molecular Formula: C12H18BNO2
• Molecular Weight: 219.091
• Hs Code.: 29319090
• European Community (EC) Number: 629-061-7
• DSSTox Substance ID: DTXSID30370400
• Nikkaji Number: J2.124.758H
• Wikidata: Q72440498
• Mol file: 214360-73-3.mol

Synonyms:2-(4-Aminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneamine;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine;

Chemical Property of 4-Aminophenylboronic acid pinacol ester

Chemical Property:

• Appearance/Colour: almost white to light beige crystalline powder
• Vapor Pressure: 8.87E-05mmHg at 25°C
• Melting Point: 165-169 °C(lit.)
• Refractive Index: 1.516
• Boiling Point: 340 °C at 760 mmHg
• PKA: 4.24±0.10(Predicted)
• Flash Point: 159.4 °C
• PSA: 44.48000
• Density: 1.05 g/cm³
• LogP: 2.14920
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Chloroform
• Water Solubility.: Insoluble
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 219.1430590
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

99% ^*data from raw suppliers

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)N
• Uses: suzuki reaction 4-Aminophenylboronic acid pinacol ester can be used as a reagent for:The preparation of substituted 3-phenyl-4H-1-benzopyran-4-ones by reacting with iodochromones via Pd catalyzed Suzuki-Miyaura cross-coupling reaction. Mercury(II) detection by fluorometry with new fluorogenic indicators based on through-bond energy transfer from pentaquinone to rhodamine. Rhodium-catalyzed amination reactions. Palladium-catalyzed Suzuki cross-coupling to synthesize potential antitubercular and antimicrobial compounds. It can also be used to prepare: Hexaphenylbenzene derivatives as a potential bioprobe and multichannel keypad system.Pyromellitic diimide-based polymer as matrix for solution-processable n-channel field-effect transistors. Alternating copolymers of oligoarylenes and naphthalene bisimides as low band-gap semiconductors with electrochemical and spectroelectrochemical behavior. γ-secretase modulators in the treatment of amyloid β formation.

Technology Process of 4-Aminophenylboronic acid pinacol ester

There total 37 articles about 4-Aminophenylboronic acid pinacol ester 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-bromo-aniline (106-40-1) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline (214360-73-3)

Guidance literature:

With 10H-phenothiazine; caesium carbonate; In acetonitrile; for 48h; Irradiation; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.9b12519

Reference yield: 96.0%

bis(pinacol)diborane (73183-34-3) + p-aminoiodobenzene (540-37-4) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline (214360-73-3)

Guidance literature:

With caesium carbonate; In methanol; for 60h; Reflux; Inert atmosphere;

DOI:10.1002/ejoc.201300829

Reference yield: 91.0%

C18H34BNO2Si2 → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline (214360-73-3)

Guidance literature:

With hydrogenchloride; water; In methanol; at 20 ℃; for 1h;

DOI:10.1039/c4sc01257g

upstream raw materials:

4-bromo-aniline

bis(pinacol)diborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

p-aminoiodobenzene

Downstream raw materials:

5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pentanamide

1-naphthalen-1-yl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-urea

4-amino-1,1':4',1'':4'',1'''-quaterphenyl

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)aminoterphenyl

Refernces

• 1、 Xue, Feng,Li, Chang-Gong,Zhu, Yong,Lou, Tian-Jun,He, Guang-Jie. "A practical and scalable process for the preparation of 4-aminophenylboronic acid pinacol ester". . p. 2739 - 2744. Retrieved 2014.
• 2、 Christopher Maumela, Munaka,Holzapfel, Cedric W.,Lamola, Jairus L.,Moshapo, Paseka T.. "Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands". supporting information. . Retrieved 2021/12/13.
• 3、 Xu, Dandan,Sun, Deqiao,Wang, Wei,Peng, Xia,Zhan, Zhengsheng,Ji, Yinchun,Shen, Yanyan,Geng, Meiyu,Ai, Jing,Duan, Wenhu. "Discovery of pyrrolo[2,3-d]pyrimidine derivatives as potent Axl inhibitors: Design, synthesis and biological evaluation". . . Retrieved 2021/05/06.