4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine

Base Information

• Chemical Name: 4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine
• CAS No.: 852227-95-3
• Molecular Formula: C16H24BNO3
• Molecular Weight: 289.182
• Hs Code.: 2934999090
• European Community (EC) Number: 801-493-2
• DSSTox Substance ID: DTXSID40400621
• Wikidata: Q82203632
• Mol file: 852227-95-3.mol

Synonyms:852227-95-3;4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine;3-morpholinophenylboronic acid pinacol ester;4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine;3-(morpholino)phenylboronic acid pinacol ester;3-Morpholinophenylboronic acid, pinacol ester;3-(4-MORPHOLINO)PHENYLBORONIC ACID PINACOL ESTER;MFCD03412097;3-MORPHOLINOPHENYLBORONIC ACID PINACOL;SCHEMBL856181;(3-MORPHOLINOPHENYL)BORONIC ACID PINACOL ESTER;DTXSID40400621;NCJDKFFODGZRRL-UHFFFAOYSA-N;4-[3-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine;AKOS015920432;AB14370;AM85928;CS-W005450;DS-1518;SY037909;FT-0755655;T3237;A22138;EN300-1674531;J-514237;Z1741978295;2-[3-(Morpholino)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-morpholine;4-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]morpholine;4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholin;4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine, AldrichCPR

Chemical Property of 4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 235 °C
• Refractive Index: 1.53
• Boiling Point: 431.51 °C at 760 mmHg
• PKA: 4.99±0.40(Predicted)
• Flash Point: 214.77 °C
• PSA: 30.93000
• Density: 1.096 g/cm³
• LogP: 1.88740
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 289.1849238
• Heavy Atom Count: 21
• Complexity: 353

Purity/Quality:

98%min ^*data from raw suppliers

4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine ^*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(=CC=C2)N3CCOCC3

Technology Process of 4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine

There total 5 articles about 4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine 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: 91.0%

bis(pinacol)diborane (73183-34-3) + 1-(3-bromophenyl)-morpholine (197846-82-5) → 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine (852227-95-3)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 80 ℃; for 6h;

DOI:10.1021/acs.jmedchem.5b00515

Reference yield: 83.0%

4-[3-[(tert-butyldimethylsilyl)oxy]phenyl]morpholine + bis(pinacol)diborane (73183-34-3) → 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine (852227-95-3)

Guidance literature:

With bis(acetylacetonate)nickel(II); lithium tert-butoxide; at 100 ℃; for 16h; Sealed tube;

DOI:10.1021/acs.orglett.1c01280

Reference yield:

1,1'-oxybis(2-bromo-ethane) (5414-19-7) + 3-aminophenylboronic acid pinacolate (210907-84-9) → 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine (852227-95-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; Reflux;

upstream raw materials:

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

bis(pinacol)diborane

1-(3-bromophenyl)-morpholine

1,1'-oxybis(2-bromo-ethane)

Downstream raw materials:

N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(3-morpholinophenyl)quinazolin-4-amine

Refernces

• 1、 Devine, William,Woodring, Jennifer L.,Swaminathan, Uma,Amata, Emanuele,Patel, Gautam,Erath, Jessey,Roncal, Norma E.,Lee, Patricia J.,Leed, Susan E.,Rodriguez, Ana,Mensa-Wilmot, Kojo,Sciotti, Richard J.,Pollastri, Michael P.. "Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery". supporting information. p. 5522 - 5537. Retrieved 2015/08/03.
• 2、 Patel, Gautam,Karver, Caitlin E.,Behera, Ranjan,Guyett, Paul J.,Sullenberger, Catherine,Edwards, Peter,Roncal, Norma E.,Mensa-Wilmot, Kojo,Pollastri, Michael P.. "Kinase scaffold repurposing for neglected disease drug discovery: Discovery of an efficacious, lapatanib-derived lead compound for trypanosomiasis". supporting information. p. 3820 - 3832. Retrieved 2013/06/27.