3-Chloro-5-methoxyphenylboronic acid

Base Information

• Chemical Name: 3-Chloro-5-methoxyphenylboronic acid
• CAS No.: 915201-07-9
• Molecular Formula: C7H8BClO3
• Molecular Weight: 186.403
• Hs Code.: 2931900090
• European Community (EC) Number: 677-318-7
• DSSTox Substance ID: DTXSID80590373
• Nikkaji Number: J2.438.842E
• Wikidata: Q72453309
• Mol file: 915201-07-9.mol

Synonyms:3-Chloro-5-methoxyphenylboronic acid;915201-07-9;(3-Chloro-5-methoxyphenyl)boronic acid;3-Chloro-5-methoxybenzeneboronic acid;3-Chloro-5-Methoxyphenylboronicacid;MFCD03095046;3-Chloro-5-methoxyphenylboronic acid;Boronic acid, (3-chloro-5-methoxyphenyl)-;3-CHLORO-5-METHOXYBENZENEBORONICACID;QBQR CG EO1;SCHEMBL519259;BORONIC ACID, B-(3-CHLORO-5-METHOXYPHENYL)-;DTXSID80590373;WAVZSRUGKKOQRB-UHFFFAOYSA-N;5-Methoxy-3-chlorophenylboronic acid;BBL100619;STL554413;3-chloro-5-methoxyphenyl boronic acid;AKOS005255154;AB13431;PS-9477;AM804544;SY122944;DB-010570;CS-0086824;W10578;3-chloro-5-methoxyphenylboronic acid, AldrichCPR;EN300-3194990;A850670;B-(3-CHLORO-5-METHOXYPHENYL)BORONIC ACID;J-512279

Chemical Property of 3-Chloro-5-methoxyphenylboronic acid

Chemical Property:

• Vapor Pressure: 8.51E-06mmHg at 25°C
• Melting Point: 185-189°C
• Refractive Index: 1.544
• Boiling Point: 359.6 °C at 760 mmHg
• PKA: 7.12±0.10(Predicted)
• Flash Point: 171.3 °C
• PSA: 49.69000
• Density: 1.32 g/cm³
• LogP: 0.02840
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 186.0255020
• Heavy Atom Count: 12
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

3-Chloro-5-methoxyphenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC(=C1)Cl)OC)(O)O
• Uses: It is used as an active pharmaceutical intermediate.

Technology Process of 3-Chloro-5-methoxyphenylboronic acid

There total 2 articles about 3-Chloro-5-methoxyphenylboronic 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-chloro-3-methoxy-benzene (2845-89-8) → (3-chloro-5-methoxyphenyl)boronic acid (915201-07-9)

Guidance literature:

1-chloro-3-methoxy-benzene; With pinacol borane; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; In cyclohexane; at 80 ℃; for 24h;

With sodium periodate; In tetrahydrofuran; water; for 0.5h;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 17h;

DOI:10.1021/ol062902w

Reference yield:

2-(3-chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (929626-16-4) → (3-chloro-5-methoxyphenyl)boronic acid (915201-07-9)

Guidance literature:

2-(3-chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; With sodium periodate; In tetrahydrofuran; water; for 0.25h;

With hydrogenchloride; In tetrahydrofuran; water; for 4h;

DOI:10.1021/ol062903o

Reference yield: 96.0%

N-methyliminodiacetic acid (4408-64-4) + (3-chloro-5-methoxyphenyl)boronic acid (915201-07-9) → C12H13BClNO5

Guidance literature:

With air; In N,N-dimethyl-formamide; at 90 ℃; for 18h; Inert atmosphere;

DOI:10.1002/anie.201406714

upstream raw materials:

1-chloro-3-methoxy-benzene

2-(3-chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Downstream raw materials:

2-(3-chloro-5-methoxyphenyl)quinoline

2-(1-(4-amino-3-(3-chloro-5-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one

2-(1-(4-amino-3-(3-chloro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one

(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-3-((2-(3-chloro-5-methoxyphenyl)-5,5-dimethylcyclohex-1-enyl)methyl)-4-methyloxazolidin-2-one

Refernces

• 1、 Murphy, Jaclyn M.,Tzschucke, C. Christoph,Hartwig, John F.. "One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes". . p. 757 - 760. Retrieved 2007/10/03.