2-Methoxypyrimidine-5-boronic acid

Base Information

• Chemical Name: 2-Methoxypyrimidine-5-boronic acid
• CAS No.: 628692-15-9
• Molecular Formula: C5H7BN2O3
• Molecular Weight: 153.933
• Hs Code.: 29349990
• European Community (EC) Number: 670-240-4
• DSSTox Substance ID: DTXSID70371597
• Nikkaji Number: J2.035.654E
• Wikidata: Q72485866
• Mol file: 628692-15-9.mol

Synonyms:2-Methoxypyrimidine-5-boronic acid;628692-15-9;(2-methoxypyrimidin-5-yl)boronic Acid;2-Methoxy-5-pyrimidineboronic acid;2-Methoxy-pyrimidine-5-boronic acid;Boronic acid, (2-methoxy-5-pyrimidinyl)-;2-methoxypyrimidin-5-ylboronic acid;2-Methoxy-5-pyrimidinylboronic Acid;MFCD03094664;2-METHOXYPYRIMIDIN-5-YL-5-BORONIC ACID;C5H7BN2O3;SCHEMBL9497;Methoxypyrimidine-5-boronic acid;DTXSID70371597;2-methoxypyrimidin-5-boronic acid;YPWAJLGHACDYQS-UHFFFAOYSA-N;2-Methoxy-5-pyrimidylboronic Acid;BCP12104;STR09909;2-methoxy-5-pyrimidine-boronic acid;2-Methoxy-5-pyrimidine boronic acid;(2-methoxypyrimidin-5-yl)boronicAcid;2-methoxy-pyrimidin-5-ylboronic acid;2-methoxypyrimidin-5-yl boronic acid;2-methoxypyrimidin-5-yl-boronic acid;2-methoxy-pyrimidin-5-yl-boronic acid;2-methoxypyrimidine-5-yl boronic acid;AKOS006228038;AC-6996;CS-W004698;PB23326;(2-methoxy pyrimidin-5-yl)boronic acid;(2-Methoxypyrimidine-5-yl)boronic acid;SY007598;[2-(methyloxy)-5-pyrimidinyl]boronic acid;A8682;AM20100542;FT-0650057;M2335;EN300-208157;J-500843;Z1201622058;2-Methoxypyrimidine-5-boronic Acid

Chemical Property of 2-Methoxypyrimidine-5-boronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 161°C(lit.)
• Refractive Index: 1.523
• Boiling Point: 378.305 °C at 760 mmHg
• PKA: 5.59±0.11(Predicted)
• Flash Point: 182.593 °C
• PSA: 75.47000
• Density: 1.335 g/cm³
• LogP: -1.83500
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 154.0549723
• Heavy Atom Count: 11
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

2-Methoxypyrimidine-5-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-41-36/37/38
• Safety Statements: 26-39-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CN=C(N=C1)OC)(O)O

Technology Process of 2-Methoxypyrimidine-5-boronic acid

There total 3 articles about 2-Methoxypyrimidine-5-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: 61.0%

5-bromo-2-methoxypyrimidine (14001-66-2) → (2-methoxypyrimidin-5-yl)boronic acid (628692-15-9)

Guidance literature:

With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexane; toluene; at -70 ℃; for 6h;

DOI:10.1039/b314624n

Reference yield: 52.0%

2-methoxy-5-(trifluoro-λ4-boraneyl)pyrimidine potassium salt → (2-methoxypyrimidin-5-yl)boronic acid (628692-15-9)

Guidance literature:

With water; silica gel; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo901441u

Reference yield:

Trimethyl borate (121-43-7,63156-11-6) + 5-bromo-2-methoxypyrimidine (14001-66-2) → (2-methoxypyrimidin-5-yl)boronic acid (628692-15-9)

Guidance literature:

5-bromo-2-methoxypyrimidine; With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; Inert atmosphere; Flow reactor;

Trimethyl borate; In tetrahydrofuran; hexane; at -30 ℃; Inert atmosphere; Flow reactor;

DOI:10.1021/acs.orglett.6b01681

upstream raw materials:

5-bromo-2-methoxypyrimidine

Trimethyl borate

Downstream raw materials:

4-(2-methoxypyrimidin-5-yl)-1,2,5,6-tetrahydro-1-tosylpyridine

3-[2-chloro-4-(2-methoxy-pyrimidin-5-yl)-phenyl]-N-hydroxy-acrylamide

C₂₁H₂₆N₆O₄

C₂₁H₂₆N₆O₄

Refernces

• 1、 Epple, Robert,Cow, Christopher,Xie, Yongping,Azimioara, Mihai,Russo, Ross,Wang, Xing,Wityak, John,Karanewsky, Donald S.,Tuntland, Tove,Nguyê?-Tran, Van T. B.,Ngo, Cara Cuc,Huang, David,Saez, Enrique,Spalding, Tracy,Gerken, Andrea,Iskandar, Maya,Seidel, H. Martin,Tian, Shin-Shay. "Novel bisaryl substituted thiazoles and oxazoles as highly potent and selective peroxisome proliferator-activated receptor δ agonists". experimental part. p. 77 - 105. Retrieved 2010/04/30.
• 2、 Saygili, Nezire,Batsanov, Andrei S.,Bryce, Martin R.. "5-Pyrimidylboronic acid and 2-methoxy-5-pyrimidylboronic acid: New heteroarylpyrimidine derivatives via Suzuki cross-coupling reactions". . p. 852 - 857. Retrieved 2007/10/03.