3-(Morpholino)phenylboronic acid

Base Information

• Chemical Name: 3-(Morpholino)phenylboronic acid
• CAS No.: 863377-22-4
• Molecular Formula: C10H14 B N O3
• Molecular Weight: 207.037
• Hs Code.: 2934999090
• European Community (EC) Number: 812-063-9
• DSSTox Substance ID: DTXSID70400619
• Wikidata: Q72492986
• Mol file: 863377-22-4.mol

Synonyms:863377-22-4;3-(Morpholino)phenylboronic acid;(3-Morpholinophenyl)boronic acid;3-Morpholinophenylboronic acid;(3-morpholin-4-ylphenyl)boronic Acid;[3-(4-Morpholinyl)phenyl]boronic acid;MFCD03412095;(3-Morpholinophenyl)boronicacid;SCHEMBL875323;DTXSID70400619;OHGOMHOEZUWGOH-UHFFFAOYSA-N;BCP07285;3-(4-Morpholinyl)phenylboronic Acid;AKOS015855893;AB14366;AM85931;CS-W008944;[3-(morpholin-4-yl)phenyl]boronic acid;B-[3-Morpholin-4-ylphenyl]boronic acid;DS-13705;SY107168;3-(morpholino)phenylboronic acid, AldrichCPR;FT-0686454;EN300-7372424;J-519664

Chemical Property of 3-(Morpholino)phenylboronic acid

Chemical Property:

• Vapor Pressure: 1.7E-08mmHg at 25°C
• Refractive Index: 1.579
• Boiling Point: 439.4°C at 760 mmHg
• PKA: 8.74±0.10(Predicted)
• Flash Point: 219.5°C
• PSA: 52.93000
• Density: 1.24
• LogP: -0.73200
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 207.1066735
• Heavy Atom Count: 15
• Complexity: 197

Purity/Quality:

99% ^*data from raw suppliers

3-Morpholinophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)N2CCOCC2)(O)O

Technology Process of 3-(Morpholino)phenylboronic acid

There total 2 articles about 3-(Morpholino)phenylboronic acid 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: 85.0%

Triisopropyl borate (5419-55-6) + 1-(3-bromophenyl)-morpholine (197846-82-5) → [3-(morpholine-4-yl)phenyl]boronic acid (863377-22-4)

Guidance literature:

1-(3-bromophenyl)-morpholine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -70 ℃; for 2h;

Triisopropyl borate; In tetrahydrofuran; hexane; at 20 ℃; Cooling with acetone-dry ice;

With water; ammonium chloride; In tetrahydrofuran; hexane;

Reference yield:

1,3-dibromobenzene (108-36-1) → [3-(morpholine-4-yl)phenyl]boronic acid (863377-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / toluene / 60 °C / Inert atmosphere

1.2: 100 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 - -70 °C

2.2: 20 °C / Cooling with acetone-dry ice

With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In tetrahydrofuran; hexane; toluene;

Reference yield: 72.04%

3-bromo-1H-indazol-5-amine (478837-59-1) + [3-(morpholine-4-yl)phenyl]boronic acid (863377-22-4) → 3-(3-morpholin-4-ylphenyl)-1H-indazol-5-amine

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 120 ℃; for 0.5h; Inert atmosphere; Microwave irradiation; Sealed tube;

upstream raw materials:

1,3-dibromobenzene

Triisopropyl borate

1-(3-bromophenyl)-morpholine

Downstream raw materials:

4-(3-(2-chloropyrimidin-4-yl)phenyl)morpholine

3-(1H-benzimidazol-2-yl)-5-(3-morpholinophenyl)pyrazin-2-amine

3-[5-(3-morpholin-4-ylphenoxy)pyrimidin-2-ylamino]-benzonitrile

2-fluoro-5-[5-(3-morpholin-4-ylphenoxy)-pyrimidin-2-ylamino]-benzo-nitrile

Refernces

• 1、 -. "COMPOUNDS". . . Retrieved 2011/12/04.