3,4-Dimethoxyphenylboronic acid

Base Information

• Chemical Name: 3,4-Dimethoxyphenylboronic acid
• CAS No.: 122775-35-3
• Molecular Formula: C8H11BO4
• Molecular Weight: 181.984
• Hs Code.: 29319090
• European Community (EC) Number: 679-694-8
• DSSTox Substance ID: DTXSID00370452
• Nikkaji Number: J1.082.420F
• Wikidata: Q72468251
• ChEMBL ID: CHEMBL349942
• Mol file: 122775-35-3.mol

Synonyms:3,4-Dimethoxyphenylboronic acid;122775-35-3;(3,4-dimethoxyphenyl)boronic acid;3,4-Dimethoxybenzeneboronic Acid;MFCD01074574;(3,4-dimethoxyphenyl)boranediol;3,4-dimethoxybenzene boronic acid;Boronic acid, (3,4-dimethoxyphenyl)-;Boronic acid, B-(3,4-dimethoxyphenyl)-;3,4-Dimethoxyphenylboronicacid;3, 4-dimethoxyphenylboronic acid;SCHEMBL23114;3,4-dimethoxyphenyboronic Acid;CHEMBL349942;3,4-Dimethoxyphenylboronic aicd;4,5-dimethoxyphenylboronic acid;3,4-dimethoxy phenylboronic acid;3,4-dimethoxy-phenylboronic acid;3,4-dimethoxyphenyl boronic acid;3,4-dimethoxyphenyl-boronic acid;DTXSID00370452;RCVDPBFUMYUKPB-UHFFFAOYSA-N;3,4-dimethoxy phenyl boronic acid;3,4-dimethoxy-phenyl boronic acid;3,4-dimethoxy-phenyl-boronic acid;BCP21797;CS-D1792;(3,4-dimethoxy phenyl)boronic acid;(3,4-dimethoxyphenyl)-boronic acid;STK503719;(3,4-dimethoxy phenyl) boronic acid;AKOS000266629;AB08049;AS-3094;[3,4-bis(methyloxy)phenyl]boronic acid;NCGC00249478-01;AC-25598;AM808127;BP-11364;SY013491;3,4-Dimethoxyphenylboronic acid, >=95.0%;D3512;FT-0614338;EN300-52543;J-511215;Z336079998

Chemical Property of 3,4-Dimethoxyphenylboronic acid

Chemical Property:

• Appearance/Colour: white to light beige powder and granules
• Vapor Pressure: 4.31E-05mmHg at 25°C
• Melting Point: 245-250 °C(lit.)
• Refractive Index: 1.517
• Boiling Point: 336.7 °C at 760 mmHg
• PKA: 8.48±0.10(Predicted)
• Flash Point: 157.4 °C
• PSA: 58.92000
• Density: 1.19 g/cm³
• LogP: -0.61640
• Storage Temp.: Keep Cold
• Water Solubility.: 25 g/L
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.0750390
• Heavy Atom Count: 13
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dimethoxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=C(C=C1)OC)OC)(O)O
• Uses: suzuki reaction 3,4-Dimethoxyphenylboronic acid can be used:As a substrate in the cross-coupling reaction with 5,7-dichloropyrido[4,3-d]pyrimidine catalyzed by palladium.As a starting material for the synthesis of buflavine 1, a natural alkaloid.In one of the key synthetic steps for the preparation of lipidated malarial glycosylphosphatidylinositols (GPI) disaccharide.To prepare 3,3″,4,4″-tetramethoxy-1,1′:4′,1″-terphenyl by reacting with 1,4-dibromobenzene using Pd catalyst.

Technology Process of 3,4-Dimethoxyphenylboronic acid

There total 8 articles about 3,4-Dimethoxyphenylboronic 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: 95.0%

2-(3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (365564-10-9) → 3,4-Dimethoxyphenylboronic acid (122775-35-3)

Guidance literature:

With hydrogenchloride; polystyrene boronic acid; In acetonitrile; at 20 ℃; for 18h;

DOI:10.1016/j.tetlet.2004.07.014

Reference yield: 87.0%

Trimethyl borate (121-43-7,63156-11-6) + 4-Bromoveratrole (2859-78-1) → 3,4-Dimethoxyphenylboronic acid (122775-35-3)

Guidance literature:

4-Bromoveratrole; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at -78 - 23 ℃; for 4h;

In tetrahydrofuran; water; at 0 - 23 ℃; pH=2;

DOI:10.1021/jacs.1c08502

Reference yield: 78.0%

4-Bromoveratrole (2859-78-1) → 3,4-Dimethoxyphenylboronic acid (122775-35-3)

Guidance literature:

4-Bromoveratrole; With n-butyllithium; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/ja907882n

upstream raw materials:

Trimethyl borate

4-Bromoveratrole

2-(3,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1,2-dimethoxybenzene

Downstream raw materials:

2-methoxy-4-(3,4-dimethoxyphenyl)-3-pivaloylaminopyridine

3-(3,4-dimethoxyphenyl)-4H-chromen-4-one

4-(3,4-Dimethoxyphenyl)-8-methoxy-5-nitroquinoline

7-(3,4-Dimethoxy-phenyl)-1H-indole

Refernces

• 1、 Daud, Hina,Hoffman, David J.,Huang, Ning,Jezorek, Ryan L.,Malineni, Jagadeesh,McClure, Emily R.,Partridge, Benjamin E.,Percec, Virgil,Peterca, Mihai,Sahoo, Dipankar,Song, Se Lin,Sung, Paul D.,Wang, Shitao,Wang, Xuefeng,Zhang, Na. "An Accelerated Modular-Orthogonal Ni-Catalyzed Methodology to Symmetric and Nonsymmetric Constitutional Isomeric AB2to AB9Dendrons Exhibiting Unprecedented Self-Organizing Principles". supporting information. p. 17724 - 17743. Retrieved 2021/11/04.
• 2、 B?uerle, Felix,Brückner, Reinhard. "Atropselective Synthesis of N,C-Bis(diphenylphosphanes) from Bridged 2-Arylindoles Based on Effective Point-to-Axial Asymmetric Inductions after an Unusual Dilithiation ⊥". supporting information. p. 9970 - 9975. Retrieved 2019/12/24.