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

Base Information

• Chemical Name: 4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine
• CAS No.: 568577-88-8
• Molecular Formula: C16H24BNO3
• Molecular Weight: 289.182
• Hs Code.: 2934999090
• European Community (EC) Number: 675-072-5
• DSSTox Substance ID: DTXSID70383635
• Nikkaji Number: J3.001.505C
• Wikidata: Q72507594
• Mol file: 568577-88-8.mol

Synonyms:568577-88-8;4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine;4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine;4-Morpholinophenylboronic acid pinacol ester;4-Morpholinophenylboronic acid, pinacol ester;MFCD04112544;MORPHOLINE, 4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]-;4-morpholin-4-ylbenzeneboronic acid pinacol ester;4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-morpholine;4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-morpholine;4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine;SCHEMBL138606;(4-MORPHOLINOPHENYL)BORONIC ACID PINACOL ESTER;DTXSID70383635;UCPALIMHMYIZPZ-UHFFFAOYSA-N;4-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-morpholine;AKOS015960098;AB17611;AM85292;AS-2425;CS-W014555;SY003840;FT-0602350;T3705;EN300-86271;A22834;A827436;4-Morpholin-4-yl-phenylboronic acid, pinacol ester;J-514242;Z1258943170;4-Morpholinophenylboronic acid, pinacol ester, AldrichCPR;1-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)-4-morpholinobenzene;N-[4(4,4,5,5-Tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-morpholine;4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine, AldrichCPR

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

Chemical Property:

• Vapor Pressure: 2.35E-07mmHg at 25°C
• Melting Point: 104℃
• Refractive Index: 1.53
• Boiling Point: 422.8 °C at 760 mmHg
• PKA: 4.65±0.40(Predicted)
• Flash Point: 209.5 °C
• PSA: 30.93000
• Density: 1.09 g/cm³
• LogP: 1.88740
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 289.1849238
• Heavy Atom Count: 21
• Complexity: 345

Purity/Quality:

98%min ^*data from raw suppliers

4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)N3CCOCC3
• Uses: 4-(4-Morpholinyl)benzeneboronic acid pinacol ester is used as pharmaceutical intermediate.

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

There total 14 articles about 4-[4-(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: 89.0%

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl morpholine-4-carboxylate → 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine (568577-88-8)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; In toluene; at 160 ℃; for 14h; Inert atmosphere; Sealed tube; Glovebox;

DOI:10.1021/jacs.9b02751

Reference yield: 86.0%

N-(4-chlorophenyl)morpholine (70291-67-7) + bis(pinacol)diborane (73183-34-3) → 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine (568577-88-8)

Guidance literature:

With tris(trimethylphosphine)nickel(II) chloride; (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; In tetrahydrofuran; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol202267t

Reference yield: 83.74%

→ 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine (568577-88-8)

Guidance literature:

upstream raw materials:

N-(4-chlorophenyl)morpholine

bis(pinacol)diborane

4-bromophenyl-morpholine

(4-bromophenyl)thioanisole

Downstream raw materials:

C₁₄H₁₆N₄O₂

Refernces

• 1、 Chernowsky, Colleen P.,Chmiel, Alyah F.,Wickens, Zachary K.,Williams, Oliver P.,Yeung, Charles S.. "Non-innocent Radical Ion Intermediates in Photoredox Catalysis: Parallel Reduction Modes Enable Coupling of Diverse Aryl Chlorides". supporting information. p. 10882 - 10889. Retrieved 2021/07/31.
• 2、 Wu, Jie,Wang, Zengwei,Chen, Xiao-Yue,Wu, Yichen,Wang, Daoming,Peng, Qian,Wang, Peng. "Para-selective borylation of monosubstituted benzenes using a transient mediator". . p. 336 - 340. Retrieved 2019/12/09.