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

Base Information

• Chemical Name: 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine
• CAS No.: 908350-80-1
• Molecular Formula: C17H20BNO2
• Molecular Weight: 281.162
• Hs Code.: 2933399090
• European Community (EC) Number: 845-970-3
• DSSTox Substance ID: DTXSID00703887
• Nikkaji Number: J3.432.039J
• Wikidata: Q72504363
• Mol file: 908350-80-1.mol

Synonyms:908350-80-1;4-(2-Pyridinyl)phenylboronic acid pinacol ester;2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine;2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine;SCHEMBL1827472;(4-(PYRIDIN-2-YL)PHENYL)BORONIC ACID PINACOL ESTER;DTXSID00703887;2-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine;BCP22851;MFCD11973624;AKOS015919539;AC-8817;AM85962;BCP9000139;DS-1667;CS-0041186;FT-0742034;EN300-317166;2-(4-PHENYLBORONIC ACID PINACOL ESTER)PYRIDINE;Z1266876560;2-[4-(2-Pyridinyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 4-(pyridin-2-yl)phenylboronate

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

Chemical Property:

• Boiling Point: 403.9±28.0 °C(Predicted)
• PKA: 4.34±0.10(Predicted)
• PSA: 31.35000
• Density: 1.09 g/cm³
• LogP: 3.04780
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 281.1587090
• Heavy Atom Count: 21
• Complexity: 348

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(2-Pyridinyl)phenylboronic acid, pinacol ester 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C3=CC=CC=N3

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

There total 7 articles about 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)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: 82.0%

2-(4-bromophenyl]pyridine (63996-36-1) + bis(pinacol)diborane (73183-34-3) → 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine (908350-80-1)

Guidance literature:

With potassium acetate; tricyclohexylphosphine; In 1,4-dioxane; for 20h; Inert atmosphere; Reflux;

Reference yield: 70.0%

4-(pyridin-2-yl)benzene-1-diazonium tetrafluoroborate + bis(pinacol)diborane (73183-34-3) → 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine (908350-80-1)

Guidance literature:

With dimanganese decacarbonyl; In acetonitrile; at 20 ℃; for 2h; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1002/chem.202004568

Reference yield: 64.0%

→ 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyridine (908350-80-1)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; Inert atmosphere;

upstream raw materials:

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(4-bromophenyl]pyridine

bis(pinacol)diborane

4-Bromophenylboronic acid

Downstream raw materials:

4-fluorophenylpyridine

Refernces

• 1、 -. "Compound with AMPK agonistic activity and preparation and application of prodrug thereof". Paragraph 0145; 0149-0150; 0229; 0233-0234. . Retrieved 2021/10/27.
• 2、 Pein, Wesley L.,Wiensch, Eric M.,Montgomery, John. "Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation". supporting information. . Retrieved 2021/06/28.