568577-88-8

Basic information

• Product Name: 4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL!MORPHOLINE
• Synonyms: 4-(MORPHOLINO)PHENYLBORONIC ACID PINACOLATE;4-MORPHOLINOPHENYLBORONIC ACID, PINACOL ESTER;4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]MORPHOLINE;4-Morpholin-4-ylbenzeneboronic acid pinacol ester;4-[4-(4,4,5,5-Tetramethyl-1,2,3-dioxaborolan-2-yl)phenyl]morpholine;4-(4-Morpholinyl)benzeneboronic acid pinacol ester, 95%;Morpholine, 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-;4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine, 2-[4-(Morpholin-4-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 568577-88-8
• Molecular Formula: C₁₆H₂₄BNO₃
• Molecular Weight: 289.18
• Product Categories: pharmacetical;Boronic Acids & Esters;Phenyls & Phenyl-Het;Boronic Acids & Esters;Phenyls & Phenyl-Het
• Mol File: 568577-88-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 98.6-99.0℃
• Boiling Point: 422.8 °C at 760 mmHg
• Flash Point: 209.5 °C
• Appearance: /
• Density: 1.09±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 2.35E-07mmHg at 25°C
• Refractive Index: 1.53
• PKA: 4.65±0.40(Predicted)
• CAS DataBase Reference: 4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL!MORPHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL!MORPHOLINE(568577-88-8)
• EPA Substance Registry System: 4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL!MORPHOLINE(568577-88-8)

Safety Data

• Hazard Codes: Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/39
• WGK Germany: 3
• Hazardous Substances Data: 568577-88-8(Hazardous Substances Data)

Usage

Uses

4-(4-Morpholinyl)benzeneboronic acid pinacol ester is used as pharmaceutical intermediate.

InChI:InChI=1/C16H24BNO3/c1-15(2)16(3,4)21-17(20-15)13-5-7-14(8-6-13)18-9-11-19-12-10-18/h5-8H,9-12H2,1-4H3

Upstream product

• 104-95-0 (4-bromophenyl)thioanisole 
• 107147-60-4 4-(morpholin-4-yl)benzenethiol 
• 180516-87-4 4-carboxyphenylboronic acid pinacol ester 
• 27347-14-4 N-(4-methoxyphenyl)morpholine 
• 73183-34-3 bis(pinacol)diborane 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 110-91-8 morpholine 
• 214360-58-4 2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 92-53-5 4-Phenylmorpholine 
• 7470-38-4 4-morpholin-4-yl-benzoic acid 
• 30483-75-1 4-bromophenyl-morpholine 
• 70291-67-7 N-(4-chlorophenyl)morpholine 

Downstream Products

• 1415309-81-7 C₁₄H₁₆N₄O₂ 
• 1333415-77-2 4-(4-((trifluoromethyl)thio)phenyl)morpholine 
• 1613260-11-9 (S)-tert-butyl 2-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yloxy)methyl)morpholine-4-carboxylate 
• 1613415-63-6 (R)-4-methyl-4-(4-morpholinophenyl)-1,2,3-oxathiazolidine 2,2-dioxide 
• 1432450-83-3 N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-6-(4-morpholinophenyl)quinazolin-4-amine 

Relevant articles and documents

Structure-based design, synthesis, and evaluation of inhibitors with high selectivity for PARP-1 over PARP-2

The poly (ADP-ribose) polymerase (PARP) inhibitors play a crucial role in cancer therapy. However, most approved PARP inhibitors have lower selectivity to PARP-1 than to PARP-2, so they will inevitably have side effects. Based on the different catalytic domains of PARP-1 and PARP-2, we developed a strategy to design and synthesize highly selective PARP-1 inhibitors. Compounds Y17, Y29, Y31 and Y49 showed excellent PARP-1 inhibition, and their IC50 values were 0.61, 0.66, 0.41 and 0.96 nM, respectively. Then, Y49 (PARP-1 IC50 = 0.96 nM, PARP-2 IC50 = 61.90 nM, selectivity PARP-2/PARP-1 = 64.5) was proved to be the most selective inhibitor of PARP-1. Compounds Y29 and Y49 showed stronger inhibitory effect on proliferation in BRCA1 mutant MX-1 cells than in other cancer cells. In the MDA-MB-436 xenotransplantation model, Y49 was well tolerated and showed remarkable single dose activity. The design strategy proposed in this paper is of far-reaching significance for the further construction of the next generation of selective PARP-1 inhibitors.

Non-innocent Radical Ion Intermediates in Photoredox Catalysis: Parallel Reduction Modes Enable Coupling of Diverse Aryl Chlorides

We describe a photocatalytic system that elicits potent photoreductant activity from conventional photocatalysts by leveraging radical anion intermediates generated in situ. The combination of an isophthalonitrile photocatalyst and sodium formate promotes diverse aryl radical coupling reactions from abundant but difficult to reduce aryl chloride substrates. Mechanistic studies reveal two parallel pathways for substrate reduction both enabled by a key terminal reductant byproduct, carbon dioxide radical anion.

Ru(II)-Catalyzed Amination of Aryl Fluorides via η6-Coordination

We developed a Ru/hemilabile-ligand-catalyzed nucleophilic aromatic substitution (SNAr) of aryl fluorides as the limiting reagents. Significant ligand enhancement was demonstrated by the engagement of both electron-rich and neutral arenes in the SNAr amination without using excess arenes. Preliminary mechanistic studies revealed that the nucleophilic substitution proceeds on a η6-complex of the Ru catalyst and the substrate, and the hemilabile ligand facilitates dissociation of products from the metal center.