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

Base Information

• Chemical Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 329214-79-1
• Molecular Formula: C11H16BNO2
• Molecular Weight: 205.065
• Hs Code.: 29333990
• European Community (EC) Number: 627-672-3
• DSSTox Substance ID: DTXSID90370426
• Nikkaji Number: J1.208.990B
• Wikidata: Q72503795
• Mol file: 329214-79-1.mol

Synonyms:329214-79-1;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;3-Pyridineboronic acid pinacol ester;Pyridine-3-boronic acid pinacol ester;3-Pyridylboronic acid pinacol ester;3-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;pyridine-3-boronic acid, pinacol ester;Pyridine, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;MFCD03084758;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine;2-(3-Pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine;3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine;3-Pyridineboronicacidpinacolester;AKOS BRN-1142;SCHEMBL369331;DTXSID90370426;XEMDFESAXKSEGI-UHFFFAOYSA-N;3-pyridyl boronic acid pinacol ester;BBL103124;RB2006;STL556934;3-pyridine boronic acid pinacol ester;3-Pyridinylboronic acid pinacol ester;AKOS004114765;AS-2663;CS-W000912;PB29225;AC-24804;SY005595;3-Pyridineboronic acid pinacol ester, 97%;A5883;AM20051073;BB 0256852;FT-0644428;PYRIDIN-3-YLBORONIC ACID PINACOL ESTER;EN300-174361;J-510642;Z1336745104;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine/3-Pyridylboronic acid pinacol ester

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

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00195mmHg at 25°C
• Melting Point: 102-104.4 °C(lit.)
• Refractive Index: 1.489
• Boiling Point: 300.9 °C at 760 mmHg
• PKA: 5.22±0.12(Predicted)
• Flash Point: 135.8 °C
• PSA: 31.35000
• Density: 1.03 g/cm³
• LogP: 1.38080
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: soluble in Acetone
• Water Solubility.: Insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 205.1274089
• Heavy Atom Count: 15
• Complexity: 227

Purity/Quality:

98% ^*data from raw suppliers

3-Pyridylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=CC=C2
• Uses: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine is an organoborane compound used in the preparation of of polyazatriaryl ligands by sequential borylation/Suzuki-Miyaura coupling. 3-Pyridineboronic Acid Pinacol E ster is used in the preparation of pyrrolo[2,3-b]pyridine derivatives as kinase modulators. 3-Pyridineboronic Acid Pinacol Ester is an organoborane compound used in the preparation of polyazatriaryl ligands by sequential borylation/Suzuki-Miyaura coupling. 3-Pyridineboronic Acid Pinacol Ester is used in the preparation of pyrrolo[2,3-b]pyridine derivatives as kinase modulators.

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

There total 27 articles about 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 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: 96.0%

3-Bromopyridine (626-55-1,163928-56-1) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (329214-79-1)

Guidance literature:

With potassium acetate; In isopropyl alcohol; at 82 ℃; for 3h;

DOI:10.1002/cctc.201301035

Reference yield: 96.0%

nicotinic acid (59-67-6) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (329214-79-1)

Guidance literature:

With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane; In 1,4-dioxane; at 160 ℃; for 15h;

DOI:10.1002/anie.201810145

Reference yield: 90.0%

3-Chloropyridine (626-60-8) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (329214-79-1)

Guidance literature:

With potassium acetate; In isopropyl alcohol; at 82 ℃; for 3h;

DOI:10.1002/cctc.201301035

upstream raw materials:

3-Chloropyridine

bis(pinacol)diborane

2,3-dimethyl-2,3-butane diol

[tris(3-pyridyl)boroxin]

Downstream raw materials:

3,3'-bipyridine

2,3'-bipyridine

4-(pyridine-3-yl)benzonitrile

3-phenylpyridine

Refernces

• 1、 K?nig, Burkhard,Wang, Hua,Wang, Shun. "Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation". supporting information. p. 1653 - 1665. Retrieved 2021/06/17.
• 2、 Demonti, Luca,Mézailles, Nicolas,Nebra, Noel,Saffon-Merceron, Nathalie. "Cross-Coupling through Ag(I)/Ag(III) Redox Manifold". supporting information. p. 15396 - 15405. Retrieved 2021/10/12.