3-Chloro-4-methoxyphenylboronic acid

Base Information

• Chemical Name: 3-Chloro-4-methoxyphenylboronic acid
• CAS No.: 175883-60-0
• Molecular Formula: C7H8BClO3
• Molecular Weight: 186.403
• Hs Code.: 29319090
• European Community (EC) Number: 691-927-5
• DSSTox Substance ID: DTXSID90390609
• Nikkaji Number: J1.642.889B
• Wikidata: Q72453311
• Mol file: 175883-60-0.mol

Synonyms:3-Chloro-4-methoxyphenylboronic acid;175883-60-0;(3-chloro-4-methoxyphenyl)boronic acid;3-Chloro-4-methoxybenzeneboronic acid;MFCD04039888;Boronic acid, (3-chloro-4-methoxyphenyl)-;(3-Chloro-4-methoxyphenyl)boronicacid;SCHEMBL9812;DTXSID90390609;VUTJHOWRPUPHIG-UHFFFAOYSA-N;BBL102675;STL556479;3-chloro-4-methoxy-phenylboronic acid;3-chloro-4-methoxyphenyl boronic acid;AKOS000285075;AB17452;CS-W000885;BP-12143;DS-15925;SY008479;[3-chloro-4-(methyloxy)phenyl]boronic acid;AM20060971;C3056;FT-0649272;Boronic acid, B-(3-chloro-4-methoxyphenyl)-;EN300-3219488;A812128;J-512242;Z381541100;3-chloro-4-methoxyphenylboronic acid (contains varying amounts of anhydride)

Chemical Property of 3-Chloro-4-methoxyphenylboronic acid

Chemical Property:

• Vapor Pressure: 1.26E-05mmHg at 25°C
• Melting Point: 238-242 °C(lit.)
• Refractive Index: 1.537
• Boiling Point: 344.8 °C at 760 mmHg
• PKA: 7.93±0.10(Predicted)
• Flash Point: 162.3 °C
• PSA: 49.69000
• Density: 1.32 g/cm³
• LogP: 0.02840
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: soluble in Methanol
• 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-4-methoxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-60-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=C(C=C1)OC)Cl)(O)O
• Uses: suzuki reaction Reactant for:Iron-catalyzed oxidative coupling with benzene derivatives through homolytic aromatic substitutionPreparation of microtubule inhibitors as potential antitumorsRhodium/chiral ligand-catalyzed arylation/Dieckmann-type annulationCopper-catalyzed oxidative N-arylationSuzuki and Stille palladium-catalyzed couplingBoron-Heck arylation

Technology Process of 3-Chloro-4-methoxyphenylboronic acid

There total 3 articles about 3-Chloro-4-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:

4-bromo-2-chloro-1-methoxybenzene (50638-47-6) → 3-chloro-4-methoxyphenylboronic acid (175883-60-0)

Guidance literature:

Reference yield:

Triisopropyl borate (5419-55-6) + 4-bromo-2-chloro-1-methoxybenzene (50638-47-6) → 3-chloro-4-methoxyphenylboronic acid (175883-60-0)

Guidance literature:

4-bromo-2-chloro-1-methoxybenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 25 ℃;

DOI:10.1016/j.ejmech.2019.111603

Reference yield:

2-Chloroanisole (766-51-8) + water (7732-18-5) + bis(pinacol)diborane (73183-34-3) → (4-chloro-3-methoxyphenyl)boronic acid (89694-47-3) + 3-chloro-4-methoxyphenylboronic acid (175883-60-0)

Guidance literature:

2-Chloroanisole; bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 0.5h; Inert atmosphere;

water; With hydrogenchloride; at 20 ℃; for 17h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00041

upstream raw materials:

4-bromo-2-chloro-1-methoxybenzene

2-Chloroanisole

water

bis(pinacol)diborane

Downstream raw materials:

1-[2-(3-chloro-4-methoxyphenyl)cyclopenten-1-yl]-4-(methylsulfonyl)benzene

3-bromo-4-(3-chloro-4-methoxyphenyl)-2(5H)-furanone

3,3'-dichloro-4,4'-dimethoxy-biphenyl

3-chloro-4-(3-chloro-4-methoxyphenyl)-2(5H)-furanone