5-Pyrimidinylboronic acid

Base Information

• Chemical Name: 5-Pyrimidinylboronic acid
• CAS No.: 109299-78-7
• Molecular Formula: C4H5BN2O2
• Molecular Weight: 123.907
• Hs Code.: 29335990
• European Community (EC) Number: 673-929-8
• DSSTox Substance ID: DTXSID70383574
• Nikkaji Number: J1.787.870K
• Wikidata: Q72504928
• Mol file: 109299-78-7.mol

Synonyms:109299-78-7;5-Pyrimidinylboronic acid;pyrimidin-5-ylboronic acid;Pyrimidine-5-boronic acid;5-pyrimidineboronic acid;5-Pyrimidylboronic Acid;(pyrimidin-5-yl)boronic acid;MFCD03002366;BORONIC ACID, 5-PYRIMIDINYL-;5-pyrimidine boronic acid;pyrimidin-5-boronic acid;pyrimidin-5-yl boronic acid;pyrimidin-5-yl-5-boronic acid;5-Pyriminylbornic acid;5-pyrimidyl-boronic acid;pyrimid-5-ylboronic acid;pyrimidin-5-ylboronicacid;pyrimidine 5-boronic acid;5-pyrimidinyl boronic acid;5-pyrimidinyl-boronic acid;pyrimidinyl-5-boronic acid;pyrimidine-5-ylboronic acid;SCHEMBL9139;pyrimidin-5-yl-boronic acid;pyrimidine-5-yl boronic acid;pyrimidine-5-yl-boronic acid;dihydroxy(5-pyrimidinyl)borane;(pyrimidin-5-yl) boronic acid;DTXSID70383574;HZFPPBMKGYINDF-UHFFFAOYSA-N;BCP27091;CS-D0207;STK503725;AKOS000264714;pyrimidine-5-boronic acid, AldrichCPR;AC-6980;PB23323;BP-10240;DS-10632;SY007735;AM20080046;FT-0642671;P1759;EN300-152345;2-AMINO-1H-BENZIMIDAZOLE-5-CARBOXYLICACID;J-002263;J-517943;F0001-0212

Chemical Property of 5-Pyrimidinylboronic acid

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 4.95E-05mmHg at 25°C
• Melting Point: 110-114 °C
• Refractive Index: 1.534
• Boiling Point: 334.7 °C at 760 mmHg
• PKA: 5.23±0.10(Predicted)
• Flash Point: 156.2 °C
• PSA: 66.24000
• Density: 1.33 g/cm³
• LogP: -1.84360
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Soluble in Ether, MeOH, DMSO, THF.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 124.0444076
• Heavy Atom Count: 9
• Complexity: 84.6

Purity/Quality:

99% ^*data from raw suppliers

5-PyrimidylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 22-26-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CN=CN=C1)(O)O
• Uses: suzuki reaction

Technology Process of 5-Pyrimidinylboronic acid

There total 2 articles about 5-Pyrimidinylboronic 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: 72.0%

5-bromopyrimidine (4595-59-9) → pyrimidine 5-boronic acid (109299-78-7)

Guidance literature:

5-bromopyrimidine; With isopropylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 2h;

With tris(trimethylsilyl)borate; In tetrahydrofuran; at 0 - 20 ℃; for 24h;

With hydrogenchloride; at 0 ℃; pH=6 - 7;

DOI:10.1081/SCC-120016325

Reference yield: 64.0%

5-bromopyrimidine (4595-59-9) + Trimethyl borate (121-43-7,63156-11-6) → pyrimidine 5-boronic acid (109299-78-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -78 - -15 ℃;

Reference yield: 93.0%

(1RS,2RS,3RS)-methyl 2-(4-bromophenyl)-3-phenylcyclopropanecarboxylate + pyrimidine 5-boronic acid (109299-78-7) → (1RS,2RS,3RS)-methyl 2-phenyl-3-(4-(pyrimidin-5-yl)phenyl)-cyclopropane carboxylate

Guidance literature:

With cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; 1,2-dimethoxyethane; at 120 ℃; for 1h; Inert atmosphere; microwave irradiation;

upstream raw materials:

5-bromopyrimidine

Trimethyl borate

Downstream raw materials:

5-(5'-Nitro-2'-thienyl)pyrimidin

3-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-4-pyrimidin-5-yl-pyrrole-2,5-dione

5-(pyridine-2-yl)pyrimidine

5-phenylpyrimidine

Refernces

• 1、 Matondo, Hubert,Souirti, Souad,Baboulene, Michel. "Improved synthesis of azaheteroarylboronic acids using tris-trimethylsilylborate under mild conditions". . p. 795 - 800. Retrieved 2003.
• 2、 -. "Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin". Page/Page column 17. . Retrieved 2008/06/13.