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

Base Information

• Chemical Name: 2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 660867-80-1
• Molecular Formula: C12H18BNO2
• Molecular Weight: 219.091
• Hs Code.: 2934999090
• European Community (EC) Number: 640-270-2
• DSSTox Substance ID: DTXSID50585998
• Nikkaji Number: J3.441.499H
• Wikidata: Q72496542
• Mol file: 660867-80-1.mol

Synonyms:660867-80-1;2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-Methylpyridine-4-boronic acid pinacol ester;MFCD08061590;PYRIDINE, 2-METHYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;SCHEMBL253320;(2-METHYLPYRIDIN-4-YL)BORONIC ACID PINACOL ESTER;2-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;DTXSID50585998;MBTULFIFECUURA-UHFFFAOYSA-N;BCP32086;2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine;AKOS005259389;AB43339;CS-W000958;2-Methylpyridine-4-boronic acid pinacol;DS-16700;SY005794;AM20061423;M2867;A25370;EN300-109705;J-509968;Z1425855882;2-methylpyridine-4-boronic acid pinacol ester, AldrichCPR;2-(2-Methyl-4-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine;2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine

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

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 0.000788mmHg at 25°C
• Melting Point: 66-71 °C
• Refractive Index: 1.489
• Boiling Point: 315.9 °C at 760 mmHg
• PKA: 5.11±0.10(Predicted)
• Flash Point: 144.8 °C
• PSA: 31.35000
• Density: 1.02 g/cm³
• LogP: 1.68920
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 219.1430590
• Heavy Atom Count: 16
• Complexity: 252

Purity/Quality:

99% ^*data from raw suppliers

2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 6 articles about 2-Methyl-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: 70.0%

4-bromo-2-methylpyridine (22282-99-1) + bis(pinacol)diborane (73183-34-3) → 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (660867-80-1)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.ejmech.2021.113554

Reference yield: 65.0%

α-picoline (109-06-8) + bis(pinacol)diborane (73183-34-3) → 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (660867-80-1)

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;

α-picoline; With C₃₂H₄₉AlBr₂O₂; In hexane; at 20 ℃; for 6h; Sealed tube;

DOI:10.1002/anie.201701238

Reference yield: 55.0%

4-chIoro-2-methylpyridine (3678-63-5) + bis(pinacol)diborane (73183-34-3) → α-picoline (109-06-8) + 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (660867-80-1)

Guidance literature:

With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel⁽⁰⁾; potassium methanolate; In hexane; at 25 ℃; for 6h; Inert atmosphere; Irradiation;

DOI:10.1021/jacs.0c08834

upstream raw materials:

4-bromo-2-methylpyridine

bis(pinacol)diborane

4-chIoro-2-methylpyridine

α-picoline

Downstream raw materials:

2-methylpyridine-4-boronic acid

6-(2-methyl-4-pyridinyl)-2-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-1,2,4-triazine-3,5(2H,4H)-dione

N-{3-(6-ethylamino-pyridin-3-yl)-1-[4-(2-methyl-pyridin-4-yl)-phenyl]-4,5-dihydro-1H-pyrazolo[4,3-g]benzothiazol-7-yl}-acetamide

N-{3-(6-methylamino-pyridin-3-yl)-1-[4-(2-methyl-pyridin-4-yl)-phenyl]-4,5-dihydro-1H-pyrazolo[4,3-g]benzothiazol-7-yl}-acetamide