5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Base Information

• Chemical Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine
• CAS No.: 827614-64-2
• Molecular Formula: C11H17BN2O2
• Molecular Weight: 220.079
• Hs Code.: 2933399990
• European Community (EC) Number: 628-581-1
• DSSTox Substance ID: DTXSID20373420
• Nikkaji Number: J2.447.056C
• Wikidata: Q72441500
• Mol file: 827614-64-2.mol

Synonyms:827614-64-2;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine;2-Aminopyridine-5-boronic acid pinacol ester;2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;6-Aminopyridine-3-boronic acid pinacol ester;2-aminopyridine-5-boronic acid, pinacol ester;5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine;MFCD05663837;2-Pyridinamine, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;C11H17BN2O2;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine;5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine;SCHEMBL183601;(6-AMINOPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;DTXSID20373420;YFTAUNOLAHRUIE-UHFFFAOYSA-N;BCP10062;RB2038;AKOS005259751;CS-W000973;GS-6327;PB24877;AC-25638;SY005789;2-aminopyridine-5-boronic acid,pinacol ester;AM20120669;FT-0647397;2-amino-pyridine-5-boronic acid pinacol ester;6-Aminopyridine-3-boronic acid, pinacol ester;EN300-97678;A840432;2-Aminopyridine-5-boronic acid pinacol ester, 97%;J-508073;Z1316857925;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridin-2-amine;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl) yridine-2-amine;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-amine;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylamine;2-amino-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine;5-(4,4,5,5-tetramethyl-[1,3,2]dioxa borolan-2-yl)-pyridin-2-ylamine;5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-ylamine;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine-2-amine

Chemical Property of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Chemical Property:

• Vapor Pressure: 3.71E-05mmHg at 25°C
• Melting Point: 131-135 °C(lit.)
• Refractive Index: 1.516
• Boiling Point: 352.9 °C at 760 mmHg
• PKA: 7.03±0.26(Predicted)
• Flash Point: 167.3 °C
• PSA: 57.37000
• Density: 1.09 g/cm³
• LogP: 1.54420
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 220.1383080
• Heavy Atom Count: 16
• Complexity: 255

Purity/Quality:

2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(C=C2)N
• Uses: 2-Aminopyridine-5-boronic acid, pinacol ester can be used in a microwave-assisted, four-component coupling process leading to amino substituted imidazopyridines. It is an important raw material and intermediate. Substrate employed in a microwave-assisted, four-component coupling process leading to amino substituted imidazopyridines.

Technology Process of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

There total 5 articles about 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 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: 99.0%

5-bromo-2-pyridylamine (1072-97-5) + bis(pinacol)diborane (73183-34-3) → 2-aminopyridine-5-boronic acid pinacol ester (827614-64-2)

Guidance literature:

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 16h; Temperature; Solvent; Inert atmosphere;

Reference yield: 77.0%

5-bromo2-nitropyridine (39856-50-3) + bis(pinacol)diborane (73183-34-3) → 2-aminopyridine-5-boronic acid pinacol ester (827614-64-2)

Guidance literature:

5-bromo2-nitropyridine; bis(pinacol)diborane; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 - 90 ℃; Inert atmosphere;

With hydrogen; In 1,4-dioxane; at 20 ℃; under 760.051 Torr;

Reference yield: 73.0%

→ 2-aminopyridine-5-boronic acid pinacol ester (827614-64-2)

Guidance literature:

With sodium hydroxide; In water; toluene; pH=8;

In water; toluene; at 20 ℃;

upstream raw materials:

5-bromo-2-pyridylamine

bis(pinacol)diborane

2-amino-5-iodopyridine

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

5-(5-(benzyloxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl)pyridin-2-amine

5-(4-(trifluoromethoxy)phenyl)pyridin-2-amine

4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine, 5,6-dihydro-1-methyl-8-(6-aminopyridin-3-yl)-6-(4-cyano-phenyl)

4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine, 5,6-dihydro-1-methyl-8-(6-aminopyridin-3-yl)-6-(4-trifluoromethyl-phenyl)

Refernces

• 1、 Arman, Hadi D.,Dang, Hang. T.,Haug, Graham C.,He, Ru,Jin, Shengfei,Larionov, Oleg V.,Nguyen, Viet D.,Nguyen, Vu T.,Schanze, Kirk S.. "Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds". supporting information. . Retrieved 2020/02/04.
• 2、 Darwish, Sarah S.,Abdel-Halim, Mohammad,Salah, Mohamed,Abadi, Ashraf H.,Becker, Walter,Engel, Matthias. "Development of novel 2,4-bispyridyl thiophene–based compounds as highly potent and selective Dyrk1A inhibitors. Part I: Benzamide and benzylamide derivatives". . p. 1031 - 1050. Retrieved 2018/09/12.