3,5-Dimethoxyphenylboronic acid

Base Information

• Chemical Name: 3,5-Dimethoxyphenylboronic acid
• CAS No.: 192182-54-0
• Molecular Formula: C8H11BO4
• Molecular Weight: 181.984
• Hs Code.: 29163990
• European Community (EC) Number: 679-693-2
• DSSTox Substance ID: DTXSID90402559
• Nikkaji Number: J852.956F
• Wikidata: Q72468244
• Mol file: 192182-54-0.mol

Synonyms:3,5-Dimethoxyphenylboronic acid;192182-54-0;3,5-Dimethoxybenzeneboronic Acid;(3,5-dimethoxyphenyl)boronic Acid;MFCD03095127;Boronic acid, (3,5-dimethoxyphenyl)-;SCHEMBL8830;3,5-DimethoxybenzeneboronicAcid;DTXSID90402559;XUIURRYWQBBCCK-UHFFFAOYSA-N;3,5-dimethoxy phenyl boronic acid;BCP34388;CS-D1032;AKOS004113962;AB13500;GS-6761;3,5-Dimethoxyphenylboronic acid, >=95%;AC-24809;SY011567;A4234;AM20050337;D3513;FT-0600757;EN300-97650;BORONIC ACID, B-(3,5-DIMETHOXYPHENYL)-;J-511339;Z1255458106

Chemical Property of 3,5-Dimethoxyphenylboronic acid

Chemical Property:

• Vapor Pressure: 2.15E-05mmHg at 25°C
• Melting Point: 205-207 °C
• Boiling Point: 371.6 °C at 760 mmHg
• PKA: 7.67±0.10(Predicted)
• Flash Point: 178.5 °C
• PSA: 58.92000
• Density: 1.19 g/cm³
• LogP: -0.61640
• Storage Temp.: Keep Cold
• Solubility.: Soluble in methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.0750390
• Heavy Atom Count: 13
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

3,5-Dimethoxy benzene boronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC(=C1)OC)OC)(O)O
• Uses: 3,5-Dimethoxyphenylboronic acid is a useful reagent for palladium-catalyst and Suzuki-Miyaura cross coupling reactions. Reactant for:Palladium-catalyzed coupling reactionsPreparation of benzopyranone derivatives as positive GABAA receptor modulatorsPreparation of aryl alkenes via three-component coupling catalyzed by palladiumSuzuki-Miyaura couplingRhodium catalyzed cyanation with N-cyano-N-phenyl-p-methylbenzenesulfonamidePreparation of bisphosphonate inhibitors of human farnesyl pyrophosphate synthase suzuki reaction

Technology Process of 3,5-Dimethoxyphenylboronic acid

There total 11 articles about 3,5-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: 92.0%

Triisopropyl borate (5419-55-6) + 1-bromo-3,5-dimethoxybenzene (20469-65-2) → 3,5-dimethoxyphenylboronic acid (192182-54-0)

Guidance literature:

1-bromo-3,5-dimethoxybenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

With sulfuric acid; In tetrahydrofuran; hexane; at 20 ℃; pH=2;

Reference yield: 81.0%

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-3,5-dimethoxybenzene (20469-65-2) → 3,5-dimethoxyphenylboronic acid (192182-54-0)

Guidance literature:

1-bromo-3,5-dimethoxybenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; ammonium chloride; In tetrahydrofuran; hexane; Inert atmosphere;

DOI:10.1002/chem.201604421

Reference yield: 65.0%

1-bromo-3,5-dimethoxybenzene (20469-65-2) → 3,5-dimethoxyphenylboronic acid (192182-54-0)

Guidance literature:

1-bromo-3,5-dimethoxybenzene; With magnesium; In tetrahydrofuran; at 80 ℃;

With Trimethyl borate; In tetrahydrofuran; at -10 - 20 ℃; for 16h;

DOI:10.1021/ja907882n

upstream raw materials:

1-bromo-3,5-dimethoxybenzene

1-iodo-3,5-dimethoxybenzene

1,3-Dimethoxybenzene

Triisopropyl borate

Downstream raw materials:

1-[(Z)-1-Fluoro-2-(4-methoxymethoxy-phenyl)-vinyl]-3,5-dimethoxy-benzene

3,5-dimethoxy-benzonitrile

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

8-(3,5-dimethoxyphenyl)-6-methoxy-2-phenethyl-1,2,3,4-tetrahydroisoquinolin-7-ol

Refernces

• 1、 Hernández-Ruiz, Raquel,Rubio-Presa, Rubén,Suárez-Pantiga, Samuel,Pedrosa, María R.,Fernández-Rodríguez, Manuel A.,Tapia, M. José,Sanz, Roberto. "Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties". supporting information. p. 13613 - 13623. Retrieved 2021/08/23.
• 2、 Liu, Hao,Su, Huan,Chen, Zhiyuan,Zhu, Senqiang,Liu, Rui,Zhu, Hongjun. "Meso-substituted boron-dipyrromethene compounds: synthesis, tunable solid-state emission, and application in blue-driven LEDs". . p. 1697 - 1705. Retrieved 2021/07/10.