4-Morpholinophenylboronic acid

Base Information

• Chemical Name: 4-Morpholinophenylboronic acid
• CAS No.: 186498-02-2
• Molecular Formula: C10H14BNO3
• Molecular Weight: 207.037
• Hs Code.: 2934999090
• European Community (EC) Number: 689-738-8
• DSSTox Substance ID: DTXSID50383633
• Nikkaji Number: J2.453.854K
• Wikidata: Q72492989
• Mol file: 186498-02-2.mol

Synonyms:4-Morpholinophenylboronic acid;186498-02-2;(4-Morpholinophenyl)boronic acid;4-(MORPHOLINO)PHENYLBORONIC ACID;(4-morpholin-4-ylphenyl)boronic Acid;4-Morpholin-4-yl-phenylboronic acid;[4-(morpholin-4-yl)phenyl]boronic acid;Boronic acid, [4-(4-morpholinyl)phenyl]-;Boronic acid, B-[4-(4-morpholinyl)phenyl]-;4-Morpholin-4-ylbenzeneboronic acid;MFCD03095169;SCHEMBL102532;4-morpholinylphenylboronic acid;(4-Morpholinophenyl)boronicacid;4-morpholino phenyl boronic acid;DTXSID50383633;WHDIUBHAKZDSJL-UHFFFAOYSA-N;4-(4-morpholinyl)phenylboronic acid;RB2002;AKOS004116180;[4-(4-morpholinyl)phenyl]boronic acid;4-Morpholin-4-yl-benzene boronic acid;AB13537;AC-1725;AM62688;AS-3096;CS-W009091;SY003839;4-morpholinophenylboronic acid, AldrichCPR;FT-0600779;A22540;EN300-145708;J-011969;J-515847;Z1509512942;4-morpholinophenylboronic acid

Chemical Property of 4-Morpholinophenylboronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 126 °C
• Refractive Index: 1.579
• Boiling Point: 425.9 °C at 760 mmHg
• PKA: 9.26±0.17(Predicted)
• Flash Point: 211.377 °C
• PSA: 52.93000
• Density: 1.243 g/cm³
• 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: 189

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Morpholin-4-yl-phenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-Morpholinophenylboronic acid

There total 6 articles about 4-Morpholinophenylboronic 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:

1,4-bromoiodobenzene (589-87-7) → 4-(4-morpholinyl)phenylboronic acid (186498-02-2) + 2-(4-bromophenyl)-3,4-dihydroisoquinolin-1(2H)-one

Guidance literature:

Multi-step reaction with 2 steps

1: sodium t-butanolate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 18-crown-6 ether; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tetrahydrofuran / 20 °C

2: n-butyllithium; Triisopropyl borate / tetrahydrofuran; ethyl acetate; pentane / -78 - 20 °C

With n-butyllithium; Triisopropyl borate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 18-crown-6 ether; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; ethyl acetate; pentane;

Reference yield:

1,4-bromoiodobenzene (589-87-7) → 4-(4-morpholinyl)phenylboronic acid (186498-02-2) + 2-(4-bromophenyl)-3,4-dihydroisoquinolin-1(2H)-one + (4-(10H-phenoxyazine-10-yl)phenyl)boronic acid

Guidance literature:

Multi-step reaction with 2 steps

1: sodium t-butanolate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 18-crown-6 ether; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tetrahydrofuran / 20 °C

2: n-butyllithium; Triisopropyl borate / tetrahydrofuran; ethyl acetate; pentane / -78 - 20 °C

With n-butyllithium; Triisopropyl borate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 18-crown-6 ether; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; ethyl acetate; pentane;

Reference yield:

1,4-bromoiodobenzene (589-87-7) → 4-(4-morpholinyl)phenylboronic acid (186498-02-2) + 2-(4-bromophenyl)-3,4-dihydroisoquinolin-1(2H)-one + (4-(10H-phenoxyazine-10-yl)phenyl)boronic acid + Phth-4-Br-L-Phe-OH

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b03455

upstream raw materials:

4-bromophenyl-morpholine

1,4-bromoiodobenzene

Downstream raw materials:

4'-morpholin-4-yl-4-trifluoromethoxy-biphenyl-3-carboxylic acid [2-cyano-1-(1H-indol-3-ylmethyl)-ethyl]-amide

N-tert-butoxycarbonyl-2-[N-tert-butoxycarbonyl-2-(4-morpholinophenyl)-1H-pyrrol-5-yl]-1H-indole

(2R)-4-methyl-N-(4-(2-methyl-4-pyridinyl)phenyl)-2-(4'-(4-morpholinyl)-3-biphenylyl)pentanamide

N-(4-(2-methylpyridin-4-yl)phenyl)-2-(4'-morpholino-[1,1'-biphenyl]-3-yl)propanamide

Refernces

• 1、 Beaumard, Floriane,Dauban, Philippe,Dodd, Robert H.. "Synthesis of nonsymmetrical 5-Aryl-2-indolopyrrole derivatives via controlled mono Suzuki-Miyaura cross-coupling on N-Boc-2,5-dibromopyrrole". experimental part. p. 4033 - 4042. Retrieved 2011/02/22.