2,6-DICHLORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE

Base Information

• Chemical Name: 2,6-DICHLORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE
• CAS No.: 408492-27-3
• Molecular Formula: C11H14BCl2NO2
• Molecular Weight: 273.955
• Hs Code.: 2934999090
• Mol file: 408492-27-3.mol

Synonyms:2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;

Chemical Property of 2,6-DICHLORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE

Chemical Property:

• Melting Point: 117-119°C
• Boiling Point: 373.232 °C at 760 mmHg
• PKA: -3.74±0.10(Predicted)
• Flash Point: 179.525 °C
• PSA: 31.35000
• Density: 1.244 g/cm³
• LogP: 2.68760
• Storage Temp.: 2-8°C

Purity/Quality:

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

2,6-Dichloropyridine-4-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,6-Dichloropyridine-4-boronic acid, pinacol ester

Technology Process of 2,6-DICHLORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE

There total 5 articles about 2,6-DICHLORO-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: 98.0%

2,6-dichloropyridine (2402-78-0) + bis(pinacol)diborane (73183-34-3) → 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (408492-27-3)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tert-butyl methyl ether; Inert atmosphere;

2,6-dichloropyridine; In tert-butyl methyl ether; at 80 ℃; for 0.05h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/ol901306m

Reference yield: 92.0%

2,6-dichloropyridine (2402-78-0) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (408492-27-3)

Guidance literature:

With iridium-bipyridine periodic mesoporous organosilica; In cyclohexane; at 80 ℃; for 12h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c5dt00239g

Reference yield: 72.0%

2,6-dichloro-4-iodopyridine (98027-84-0) + bis(pinacol)diborane (73183-34-3) → 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (408492-27-3)

Guidance literature:

With trans-bis(triphenylphosphine)palladium dichloride; potassium acetate; In N,N-dimethyl-formamide; at 100 ℃; for 1h; Inert atmosphere;

upstream raw materials:

2,6-dichloropyridine

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

bis(pinacol)diborane

2,6-dichloro-4-iodopyridine

Downstream raw materials:

methyl 4-(2,6-dichloropyridin-4-yl)benzoate

2,2',6,6'-tetrachloro-4,4'-bipyridine

2,6-dichloro-4-cyanopyridine

tert-butyl 4-(2,6-dichloropyridin-4-yl)-5 ,6-dihydropyridine-1(2H)-carboxylate

Refernces

• 1、 Ikemoto, Koki,Isobe, Hiroyuki,Matsuno, Taisuke,Miyachi, Akira,Muto, Hitomi,Sasakawa, Hiroaki,Yang, Seungmin. "Metal-Templated Oligomeric Macrocyclization via Coupling for Metal-Doped π-Systems". supporting information. p. 15017 - 15021. Retrieved 2021/09/30.
• 2、 Ding, Siyi,Wang, Linghua,Miao, Zongcheng,Li, Pengfei. "NNB-type tridentate boryl ligands enabling a highly active iridium catalyst for C–H borylation". . . Retrieved 2019/04/30.