3-CHLORO-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE

Base Information

• Chemical Name: 3-CHLORO-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE
• CAS No.: 458532-90-6
• Molecular Formula: C11H15BClNO2
• Molecular Weight: 239.51
• Hs Code.: 2934999090
• Mol file: 458532-90-6.mol

Synonyms:3-Chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine;3-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;

Chemical Property of 3-CHLORO-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE

Chemical Property:

• Vapor Pressure: 0.000466mmHg at 25°C
• Melting Point: 86-90ºC
• Refractive Index: 1.505
• Boiling Point: 324.4 °C at 760 mmHg
• Flash Point: 150 °C
• PSA: 31.35000
• Density: 1.14 g/cm³
• LogP: 2.03420
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

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

3-Chloropyridine-4-boronic acid pinacol ester ^*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

Total 1 MSDS from other Authors

Useful:

• Uses: 3-Chloropyridine-4-boronic acid, pinacol ester

Technology Process of 3-CHLORO-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE

There total 4 articles about 3-CHLORO-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: 51.0%

3-Chloropyridine (626-60-8) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 3-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (458532-90-6)

Guidance literature:

3-Chloropyridine; With n-butyllithium; diisopropylamine; In diethyl ether; at -60 ℃; for 0.75h;

With Triisopropyl borate; In diethyl ether; at -60 - 10 ℃;

2,3-dimethyl-2,3-butane diol; With acetic acid; In diethyl ether; for 4h;

DOI:10.1016/S0040-4020(02)00416-7

Reference yield:

3-Chloropyridine (626-60-8) → 3-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (458532-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / -78 °C

2: hexane; tetrahydrofuran / -78 - 20 °C

With lithium diisopropyl amide; In tetrahydrofuran; hexane;

DOI:10.1021/jo0620359

Reference yield:

C11H17ClNO2B + 2,3-dimethyl-2,3-butane diol (76-09-5) → 3-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine (458532-90-6)

Guidance literature:

In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/jo0620359

upstream raw materials:

3-Chloropyridine

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

Downstream raw materials:

3'-chloro-2-(2-fluorophenyl)-5-nitro-3,4'-bipyridin-6-amine

3-chloro-4-phenylpyridine

Refernces

• 1、 Alessi, Manlio,Larkin, Andrew L.,Ogilvie, Kevin A.,Green, Laine A.,Lai, Sunny,Lopez, Simon,Snieckus, Victor. "Directed ortho metalation-boronation and Suzuki-Miyaura cross coupling of pyridine derivatives: A one-pot protocol to substituted azabiaryls". . p. 1588 - 1594. Retrieved 2008/02/03.