3-Aminophenylboronic acid pinacol ester

Base Information

• Chemical Name: 3-Aminophenylboronic acid pinacol ester
• CAS No.: 210907-84-9
• Molecular Formula: C12H18BNO2
• Molecular Weight: 219.091
• Hs Code.: 29310099
• European Community (EC) Number: 626-895-3
• DSSTox Substance ID: DTXSID30370425
• Nikkaji Number: J1.208.987B
• Wikidata: Q72440495
• Mol file: 210907-84-9.mol

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

Chemical Property of 3-Aminophenylboronic acid pinacol ester

Chemical Property:

• Appearance/Colour: light brown crystals or powder
• Vapor Pressure: 4.16E-05mmHg at 25°C
• Melting Point: 89-94 °C
• Refractive Index: 1.516
• Boiling Point: 351.238 °C at 760 mmHg
• PKA: 4.56±0.10(Predicted)
• Flash Point: 166.223 °C
• PSA: 44.48000
• Density: 1.051 g/cm³
• LogP: 2.14920
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: very soluble in Methanol
• 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: 252

Purity/Quality:

98% ^*data from raw suppliers

3-Aminophenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC=C2)N
• Uses: 3-Aminophenylboronic acid pinacol ester can be used:As a starting material for the synthesis of 6-(hetero)arylthieno[3,2-b]pyridines, which are known to inhibit human tumor cells selectively.In the functionalization of deuteroporphyrin IX dimethyl ester through Suzuki-Miyaura coupling.To prepare benzo[d]oxazole based type-I FLT3-ITD inhibitors.

Technology Process of 3-Aminophenylboronic acid pinacol ester

There total 28 articles about 3-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: 100.0%

m-Bromoaniline (591-19-5) + bis(pinacol)diborane (73183-34-3) → 3-aminophenylboronic acid pinacolate (210907-84-9)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; for 2.75h; Inert atmosphere; Reflux;

Reference yield: 96.0%

4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane (68716-48-3) → 3-aminophenylboronic acid pinacolate (210907-84-9)

Guidance literature:

With hydrogen; at 100 ℃; for 12h; under 7500.75 Torr; Sealed tube; Autoclave;

DOI:10.1002/cctc.202100045

Reference yield: 96.0%

3-aminophenyl tosylate (3865-15-4) + bis(pinacol)diborane (73183-34-3) → 3-aminophenylboronic acid pinacolate (210907-84-9)

Guidance literature:

With potassium acetate; In tert-butyl alcohol; at 90 ℃; for 18h; Inert atmosphere;

DOI:10.1002/chem.201100361

upstream raw materials:

m-Bromoaniline

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

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

3-aminobenzeneboronic acid monohydrate

Downstream raw materials:

[1-Anthracen-9-yl-meth-(E)-ylidene]-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amine

[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-[1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-meth-(E)-ylidene]-amine

[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-[1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-eth-(E)-ylidene]-amine

[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-[1-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-meth-(E)-ylidene]-amine

Refernces

• 1、 Watterson, Scott H.,Liu, Qingjie,Beaudoin Bertrand, Myra,Batt, Douglas G.,Li, Ling,Pattoli, Mark A.,Skala, Stacey,Cheng, Lihong,Obermeier, Mary T.,Moore, Robin,Yang, Zheng,Vickery, Rodney,Elzinga, Paul A.,Discenza, Lorell,D'Arienzo, Celia,Gillooly, Kathleen M.,Taylor, Tracy L.,Pulicicchio, Claudine,Zhang, Yifan,Heimrich, Elizabeth,McIntyre, Kim W.,Ruan, Qian,Westhouse, Richard A.,Catlett, Ian M.,Zheng, Naiyu,Chaudhry, Charu,Dai, Jun,Galella, Michael A.,Tebben, Andrew J.,Pokross, Matt,Li, Jianqing,Zhao, Rulin,Smith, Daniel,Rampulla, Richard,Allentoff, Alban,Wallace, Michael A.,Mathur, Arvind,Salter-Cid, Luisa,Macor, John E.,Carter, Percy H.,Fura, Aberra,Burke, James R.,Tino, Joseph A.. "Discovery of Branebrutinib (BMS-986195): A Strategy for Identifying a Highly Potent and Selective Covalent Inhibitor Providing Rapid in Vivo Inactivation of Bruton's Tyrosine Kinase (BTK)". . . Retrieved 2019.
• 2、 Annisa, Tiara Nur,Lee, Hyung-il. "Water-Soluble Polymeric Probes for the pH-Tunable Fluorometric Detection of Hydrogen Peroxide". . p. 537 - 541. Retrieved 2020.
• 3、 K?nig, Burkhard,Wang, Hua,Wang, Shun. "Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation". supporting information. p. 1653 - 1665. Retrieved 2021/06/17.
• 4、 Forster, Michael,Liang, Xiaojun Julia,Schr?der, Martin,Gerstenecker, Stefan,Chaikuad, Apirat,Knapp, Stefan,Laufer, Stefan,Gehringer, Matthias. "Discovery of a novel class of covalent dual inhibitors targeting the protein kinases bmx and btk". . p. 1 - 36. Retrieved 2020/12/15.