2,6-Dimethoxyphenylboronic acid

Base Information

• Chemical Name: 2,6-Dimethoxyphenylboronic acid
• CAS No.: 23112-96-1
• Molecular Formula: C8H11BO4
• Molecular Weight: 181.984
• Hs Code.: 29319090
• European Community (EC) Number: 679-862-0
• DSSTox Substance ID: DTXSID40370234
• Nikkaji Number: J1.326.102D
• Wikidata: Q72468254
• Mol file: 23112-96-1.mol

Synonyms:2,6-Dimethoxyphenylboronic acid;23112-96-1;(2,6-dimethoxyphenyl)boronic acid;2,6-Dimethoxybenzeneboronic Acid;MFCD01318987;Boronic acid, (2,6-dimethoxyphenyl)-;2,6-DIMETHOXYPHENYL-BORONIC ACID;2,6-Dimethoxyphenylboronicacid;AF-399/25108058;SCHEMBL203282;2,6-dimethoxy-phenylboronic acid;2,6-dimethoxyphenyl boronic acid;DTXSID40370234;2,6-dimethoxybenzene boronic acid;BKWVXPCYDRURMK-UHFFFAOYSA-N;(2,6-dimethoxy)phenylboronic acid;BCP19585;AKOS002663425;AB08798;AM86786;B-(2,6-Dimethoxy-phenyl)boronic acid;CS-W019869;GS-6777;NCGC00249518-01;AC-24791;Boronic acid, B-(2,6-dimethoxyphenyl)-;BP-12137;SY017987;A4891;D3861;FT-0638295;EN300-119838;J-507496;Z1203159460

Chemical Property of 2,6-Dimethoxyphenylboronic acid

Chemical Property:

• Appearance/Colour: white to beige powder
• Vapor Pressure: 3.22E-06mmHg at 25°C
• Melting Point: 110-112 °C(lit.)
• Refractive Index: 1.517
• Boiling Point: 372.8 °C at 760 mmHg
• PKA: 8.58±0.58(Predicted)
• Flash Point: 179.3 °C
• PSA: 58.92000
• Density: 1.19 g/cm³
• LogP: -0.61640
• Storage Temp.: Keep Cold
• 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:

98% ^*data from raw suppliers

2,6-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=C(C=CC=C1OC)OC)(O)O
• Uses: 2,6-Dimethoxyphenylboronic acid can be used as a reagent in:The palladium-catalyzed Suzuki-Miyaura coupling reaction to construct carbon-carbon bond.The synthesis of 2H-imidazo[1,5-a]pyridin-4-ium bromides, which are utilized as precursors for the preparation of N-heterocyclic carbene ligands.The preparation of monosubstituted benzothiazoloquinazolinones as potential monoamine oxidases inhibitors.Reactant for:Suzuki-Miyaura reactions

Technology Process of 2,6-Dimethoxyphenylboronic acid

There total 10 articles about 2,6-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: 94.0%

Trimethyl borate (121-43-7,63156-11-6) + 1,3-Dimethoxybenzene (151-10-0) → (2,6-dimethoxyphenyl)boronic acid (23112-96-1)

Guidance literature:

1,3-Dimethoxybenzene; With biphenyl; 2-methylchlorobenzene; lithium; In tetrahydrofuran; at 0 ℃; for 6h;

Trimethyl borate; In tetrahydrofuran; at -50 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; water; pH=6.3;

Reference yield: 82.0%

→ (2,6-dimethoxyphenyl)boronic acid (23112-96-1)

Guidance literature:

With magnesium; ethylene dibromide; In tetrahydrofuran; at 40 - 60 ℃; Inert atmosphere;

In tetrahydrofuran; for 6h; Inert atmosphere; Reflux;

Reference yield: 80.0%

Triisopropyl borate (5419-55-6) + 1-bromo-2,6-dimethoxybenzene (16932-45-9) → (2,6-dimethoxyphenyl)boronic acid (23112-96-1)

Guidance literature:

1-bromo-2,6-dimethoxybenzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 3h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃;

upstream raw materials:

Trimethyl borate

1,3-Dimethoxybenzene

C₁₀H₁₅BO₄

Triisopropyl borate

Downstream raw materials:

2,6-Dimethoxybenzolborsaeure-n-butylester

C₈H₁₀BFO₄

2-(2,6-dimethoxy-phenyl)-4-methoxy-6-methyl-5-nitro-pyrimidine

(S)-2-trifluoroacetamido-5-(2,6-dimethoxyphenyl)tetralin

Refernces

• 1、 -. "Aryl boronic acid preparation method". Paragraph 0033-0036; 0040. . Retrieved 2020/01/25.
• 2、 -. "Organic Compound for organic light emitting diode and an organic light emitting diode including the same". Paragraph 0611-0617; 0707-0713. . Retrieved 2019/06/04.