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

Base Information

• Chemical Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 181219-01-2
• Molecular Formula: C11H16BNO2
• Molecular Weight: 205.065
• Hs Code.: 29349990
• European Community (EC) Number: 628-005-9
• DSSTox Substance ID: DTXSID60370418
• Nikkaji Number: J871.098H
• Wikidata: Q72503792
• Mol file: 181219-01-2.mol

Synonyms:181219-01-2;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;4-Pyridineboronic acid pinacol ester;Pyridine-4-boronic acid pinacol ester;Pyridine-4-boronic acid, pinacol ester;MFCD01319051;4-Pyridylboronic acid pinacol ester;4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;Pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;2-(4-Pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine;pyridine-4-boronic acid pinacol cyclic ester;SCHEMBL321437;DTXSID60370418;NLTIETZTDSJANS-UHFFFAOYSA-N;Pyridine-4-boronic acid pinacolate;4-pyridinylboronic acid pinacol ester;BBL101582;STL555378;4-pyridine boronic acid pinacol ester;4-pyridinyl boronic acid pinacol ester;AKOS004119232;CS-W002770;GS-6755;PB27534;pyridine4boronic acid pinacol cyclic ester;SY007969;4-Pyridineboronic acid pinacol ester, 97%;AM20050894;FT-0643746;T2349;EN300-69714;PYRIDIN-4-YLBORONIC ACID PINACOL ESTER;A22428;J-011572;J-513430;Z1117899666;4-(4,4,5,5-tetramethyl-[1,3]dioxaborolan-2-yl)-pyridine;2-(4-PYRIDYL)-4,4,5,5-TETRAMETHYL-1,3-DIOXABOROLANE;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine;4-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)-pyridine;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine;4-(4,4,5,5-Tetramethyl-1.3.2-dioxaborolan-2-yl)pyridine;4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)pyridine;2-(PYRIDIN-4-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

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

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 0.00195mmHg at 25°C
• Melting Point: 149-153 °C(lit.)
• Refractive Index: 1.489
• Boiling Point: 300.902 °C at 760 mmHg
• PKA: 4.32±0.10(Predicted)
• Flash Point: 135.781 °C
• PSA: 31.35000
• Density: 1.035 g/cm³
• LogP: 1.38080
• Storage Temp.: Refrigerator (+4°C)
• 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: 221

Purity/Quality:

98% ^*data from raw suppliers

4-Pyridineboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C,F
• Hazard Codes: Xi,C,F
• Statements: 36/37/38-34-11
• Safety Statements: 26-36-45-36/37/39-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=NC=C2
• Uses: 4-Pyridineboronic Acid Pinacol ester is used in dermatological preparations containing antioxidants and boron compounds for preventing damages to skin caused by peroxides. It is employed in the synthesis of new pyridazino[4,5-b]indol-4-ones and pyridazin-3(2H)-one analogs as DYRK1A inhibitors.

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

There total 15 articles about 4-(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: 100.0%

4-pyridylboronic acid (1692-15-5) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 4-pyridineboronic acid pinacol ester (181219-01-2)

Guidance literature:

In 1,4-dioxane; for 18h; Molecular sieve; Reflux;

DOI:10.1016/j.jfluchem.2008.12.006

Reference yield: 79.0%

pyridine (110-86-1) + bis(pinacol)diborane (73183-34-3) → 3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1012085-50-5) + 4-pyridineboronic acid pinacol ester (181219-01-2)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In hexane; at 60 ℃; for 0.5h; Inert atmosphere; Glovebox; Sealed tube;

pyridine; With C₃₂H₄₉AlBr₂O₂; In hexane; at 20 ℃; for 16h; Reagent/catalyst; Sealed tube;

DOI:10.1002/anie.201701238

Reference yield: 75.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-iodopyridine (15854-87-2) + boric acid tributyl ester (688-74-4) → 4-pyridineboronic acid pinacol ester (181219-01-2)

Guidance literature:

4-iodopyridine; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.5h;

boric acid tributyl ester; In diethyl ether; hexane; at -78 - 20 ℃; for 2h;

2,3-dimethyl-2,3-butane diol; In diethyl ether; hexane; for 0.5h;

DOI:10.1039/d0ce01020k

upstream raw materials:

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

pyridine

bis(pinacol)diborane

4-iodopyridine

Downstream raw materials:

4,4'-di(4-pyridyl)biphenyl

C₅H₄NC₁₈H₁₂C₅H₄N

4-(2-pyridyl)pyridine

4-[4-(4-bromophenoxy)phenyl]pyridine

Refernces

• 1、 Al-Shehimy, Shaymaa,Gramage-Doria, Rafael,Roisnel, Thierry,Trouvé, Jonathan,Zardi, Paolo. "Enzyme-like Supramolecular Iridium Catalysis Enabling C?H Bond Borylation of Pyridines with meta-Selectivity". supporting information. p. 18006 - 18013. Retrieved 2021/05/07.
• 2、 Lemmerz, Lara E.,Mukherjee, Debabrata,Spaniol, Thomas P.,Wong, Anthony,Ménard, Gabriel,Maron, Laurent,Okuda, Jun. "Cationic magnesium hydride [MgH]+ stabilized by an NNNN-type macrocycle". supporting information. p. 3199 - 3202. Retrieved 2019/05/08.