(4-Hydroxy-3-methoxyphenyl)boronic acid

Base Information

• Chemical Name: (4-Hydroxy-3-methoxyphenyl)boronic acid
• CAS No.: 182344-21-4
• Molecular Formula: C7H9 B O4
• Molecular Weight: 167.957
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID70468512
• Nikkaji Number: J2.239.181J
• Wikidata: Q82295740
• Mol file: 182344-21-4.mol

Synonyms:182344-21-4;(4-Hydroxy-3-methoxyphenyl)boronic acid;4-HYDROXY-3-METHOXYPHENYLBORONIC ACID;Boronic acid, (4-hydroxy-3-methoxyphenyl)- (9CI);Boronic acid, B-(4-hydroxy-3-methoxyphenyl)-;Boronic acid, (4-hydroxy-3-methoxyphenyl)-;SCHEMBL11322;DTXSID70468512;UZFBWSFTHSYXCN-UHFFFAOYSA-N;MFCD18397223;3-Methoxy-4-hydroxyphenylboronic acid;AKOS015893241;(4-Hydroxy-3-methoxyphenyl)boronicacid;4-Hydroxy-3-methoxybenzeneboronic acid;AS-55548;CS-0044961;FT-0760391;EN300-268996;Y13466;A880902

Chemical Property of (4-Hydroxy-3-methoxyphenyl)boronic acid

Chemical Property:

• PSA: 69.92000
• LogP: -0.91940
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.0593889
• Heavy Atom Count: 12
• Complexity: 141

Purity/Quality:

98% ^*data from raw suppliers

4-Hydroxy-3-methoxyphenylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=C(C=C1)O)OC)(O)O
• Uses: 4-Hydroxy-3-methoxyphenylboronic acid is a useful reagent for organic synthesis and other chemical processes. It is used as a reagent in the synthesis of 4-arylcoumarins with antiprotozoal activity via Suzuki-Miyaura cross-coupling reaction, and in the direct palladium-catalyzed C-H functionalization of benzoquinones.

Technology Process of (4-Hydroxy-3-methoxyphenyl)boronic acid

There total 2 articles about (4-Hydroxy-3-methoxyphenyl)boronic 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:

2-(4-bromo-2-methoxyphenoxy)tetrahydropyran (864757-97-1) → (4-hydroxy-3-methoxyphenyl)boronic acid (182344-21-4)

Guidance literature:

2-(4-bromo-2-methoxyphenoxy)tetrahydropyran; With n-butyllithium; In tetrahydrofuran; hexane; at -65 ℃; for 0.166667h;

With Triisopropyl borate; In tetrahydrofuran; at -65 ℃; for 0.166667h;

With hydrogenchloride; In water;

DOI:10.1016/j.tet.2005.08.043

Reference yield:

4-bromoguaiacol (7368-78-7) → (4-hydroxy-3-methoxyphenyl)boronic acid (182344-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 75 percent / hydrochloric acid / acetonitrile / 24 h / 20 °C

2.1: n-buthyllithium / hexane; tetrahydrofuran / 0.17 h / -65 °C

2.2: triisopropyl borate / tetrahydrofuran / 0.17 h / -65 °C

2.3: hydrochloric acid / H₂O

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1016/j.tet.2005.08.043

Reference yield: 85.0%

methyl 5-(5-{5-[5-bromo-3-(2-methoxy-2-oxoethyl)thiophen-2-yl]thiophen-2-yl}-4-(2-methoxy-2-oxoethyl)thiophen-2-yl)thiophene-2-carboxylate (1419171-68-8) + (4-hydroxy-3-methoxyphenyl)boronic acid (182344-21-4) → C31H26O8S4 (1419172-37-4)

Guidance literature:

With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In methanol; toluene; at 80 ℃; for 0.166667h; Inert atmosphere; Sealed tube;

upstream raw materials:

2-(4-bromo-2-methoxyphenoxy)tetrahydropyran

4-bromoguaiacol

Downstream raw materials:

4-hydroxy-3-methoxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside

C₃₆H₄₂N₆O₆

4-(4'-hydroxy-3'-methoxyphenyl)-6,7-dimethoxycoumarin

Refernces