2,6-Dimethoxypyridine-3-boronic acid

Base Information

• Chemical Name: 2,6-Dimethoxypyridine-3-boronic acid
• CAS No.: 221006-70-8
• Molecular Formula: C7H10BNO4
• Molecular Weight: 182.972
• Hs Code.: 2933399090
• European Community (EC) Number: 623-227-2
• DSSTox Substance ID: DTXSID30376381
• Nikkaji Number: J2.448.794F
• Wikidata: Q72468492
• Mol file: 221006-70-8.mol

Synonyms:221006-70-8;2,6-Dimethoxypyridine-3-boronic acid;2,6-Dimethoxypyridin-3-ylboronic acid;(2,6-dimethoxypyridin-3-yl)boronic Acid;2,6-Dimethoxy-3-pyridineboronic acid;MFCD03788239;Boronic acid, (2,6-dimethoxy-3-pyridinyl)-;(2,6-DIMETHOXY-3-PYRIDYL)BORONIC ACID;2,6-Dimethoxy-3-pyridylboronic Acid;2,6-Dimethoxypyridine-3-Boroni;SCHEMBL321488;AMY7884;DTXSID30376381;ADGHSWFUZUADDH-UHFFFAOYSA-N;2,6-dimethoxypyridin-3-boronic acid;BBL102103;STL555902;2,6-Dimethoxypyridin-3-ylboronicacid;2,6-dimethoxy-pyridin-3-boronic acid;AKOS015851914;2,6-dimethoxy-3-pyridine boronic acid;2,6-dimethoxy-pyridine-3-boronic acid;AB15941;CS-W000902;RS-1019;2,6-dimethoxypyridin-3-yl boronic acid;(2,6-dimethoxy-3-pyridinyl)boronic acid;2,6-dimethoxy-pyridin-3-yl boronic acid;AC-33466;SY022304;2,6-dimethoxy -pyridin-3-yl boronic acid;D4690;FT-0644039;2,6-DIMETHOXYPYRIDINE-5-BORONIC ACID;[2,6-bis(methyloxy)-3-pyridinyl]boronic acid;EN300-7367884;A815922;J-500610

Chemical Property of 2,6-Dimethoxypyridine-3-boronic acid

Chemical Property:

• Vapor Pressure: 3.14E-05mmHg at 25°C
• Melting Point: 128-130 °C
• Refractive Index: 1.517
• Boiling Point: 341.2 °C at 760 mmHg
• PKA: 7.28±0.58(Predicted)
• Flash Point: 160.2 °C
• PSA: 71.81000
• Density: 1.26 g/cm³
• LogP: -1.22140
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 183.0702880
• Heavy Atom Count: 13
• Complexity: 157

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,6-Dimethoxypyridine-3-boronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(N=C(C=C1)OC)OC)(O)O
• Uses: Reactant for:Preparation of benzopyranone derivatives as positive GABAA receptor modulatorsPreparation of pyrazine derivatives as orally active corticotropin releasing factor-1 receptor antagonistsMicrowave-enhanced synthesis of trisubstituted pyridazinesPreparation of biaryl derivatives via palladium-catalyzed Suzuki-Miyaura cross-coupling reaction with aryl- or heteroaryl halidesPreparation of 3-arylpyridines via palladium-P Phos catalyzed Suzuki cross coupling

Technology Process of 2,6-Dimethoxypyridine-3-boronic acid

There total 3 articles about 2,6-Dimethoxypyridine-3-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: 82.0%

2,6-dimethoxypyridine (6231-18-1,122797-02-8) → 2,6-dimethoxypyridine-3-boronic acid (221006-70-8)

Guidance literature:

2,6-dimethoxypyridine; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With hydrogen bromide; In water; pH=6;

DOI:10.1002/ejoc.200701156

Reference yield: 61.0%

2,6-dimethoxypyridine (6231-18-1,122797-02-8) + Triisopropyl borate (5419-55-6) → 2,6-dimethoxypyridine-3-boronic acid (221006-70-8)

Guidance literature:

2,6-dimethoxypyridine; With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -40 - 0 ℃; for 3h;

Triisopropyl borate; In tetrahydrofuran; at -40 - 20 ℃; for 1h;

Reference yield:

3-bromo-2,6-dimethoxypyridine (13445-16-4) + Triisopropyl borate (5419-55-6) + water (7732-18-5) → 2,6-dimethoxypyridine-3-boronic acid (221006-70-8)

Guidance literature:

3-bromo-2,6-dimethoxypyridine; With n-butyllithium; In tetrahydrofuran; toluene; at -78 ℃; for 3.5h; Inert atmosphere; Schlenk technique;

Triisopropyl borate; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 21h; Inert atmosphere; Schlenk technique;

water; With acetic acid; In tetrahydrofuran; toluene; at 20 ℃; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c4tc00542b

upstream raw materials:

2,6-dimethoxypyridine

3-bromo-2,6-dimethoxypyridine

Triisopropyl borate

water

Downstream raw materials:

2',6'-dimethoxy-[2,3']bipyridinyl-4-ylamine

2,6-dimethoxy-3-(4-methoxyphenyl)pyridine

2,6-dimethoxy-3-phenylpyridine

2,6-dimethoxy-3-(4-methylphenyl)pyridine

Refernces

• 1、 Sutherland, Hamish S.,Tong, Amy S.T.,Choi, Peter J.,Blaser, Adrian,Conole, Daniel,Franzblau, Scott G.,Lotlikar, Manisha U.,Cooper, Christopher B.,Upton, Anna M.,Denny, William A.,Palmer, Brian D.. "3,5-Dialkoxypyridine analogues of bedaquiline are potent antituberculosis agents with minimal inhibition of the hERG channel". supporting information. p. 1292 - 1307. Retrieved 2019/02/25.
• 2、 Evariste, Sloane,Sandroni, Martina,Rees, Thomas W.,Roldan-Carmona, Cristina,Gil-Escrig, Lidon,Bolink, Henk J.,Baranoff, Etienne,Zysman-Colman, Eli. "Fluorine-free blue-green emitters for light-emitting electrochemical cells". . p. 5793 - 5804. Retrieved 2014/07/22.