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

Base Information

• Chemical Name: 2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 444120-94-9
• Molecular Formula: C11H15BClNO2
• Molecular Weight: 239.51
• Hs Code.: 2933399090
• European Community (EC) Number: 624-473-3
• DSSTox Substance ID: DTXSID40383349
• Nikkaji Number: J2.142.726H
• Wikidata: Q72458430
• Mol file: 444120-94-9.mol

Synonyms:444120-94-9;2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-Chloropyridine-5-boronic Acid Pinacol Ester;2-Chloro-5-pyridylboronic acid pinacol ester;2-Chloropyridine-5-boronic acid, pinacol ester;6-Chloro-3-pyridineboronic acid pinacol ester;Pyridine, 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;MFCD03412793;2-(6-Chloro-3-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Chloro-5-pyridineboronic acid pinacol ester;6-Chloropyridine-3-boronic acid pinacol ester;SCHEMBL1602392;(6-CHLOROPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;2-chloro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;DTXSID40383349;IEFBTHROULVUAH-UHFFFAOYSA-N;BCP14073;AKOS004116432;AB14436;AC-7287;AS-2375;CS-W003058;SY005488;AM20051185;C3136;FT-0644685;EN300-1073076;6-Chloro-3-pyridineboronic acid pinacol ester, 97%;Z1741978314;2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine

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

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 0.000364mmHg at 25°C
• Melting Point: 86-90 °C
• Refractive Index: 1.505
• Boiling Point: 328.3 °C at 760 mmHg
• PKA: 0.17±0.10(Predicted)
• Flash Point: 152.4 °C
• PSA: 31.35000
• Density: 1.14 g/cm³
• LogP: 2.03420
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 239.0884366
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

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

2-Chloropyridine-5-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36-20/21/22
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(C=C2)Cl

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

There total 10 articles about 2-Chloro-5-(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: 87.0%

5-bromo-2-chloropyridine (53939-30-3) + bis(pinacol)diborane (73183-34-3) → 2-chloro-5-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (444120-94-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In N,N-dimethyl-formamide; for 4h; Inert atmosphere; Reflux;

Reference yield: 71.0%

5-bromo-2-chloropyridine (53939-30-3) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 2-chloro-5-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (444120-94-9)

Guidance literature:

5-bromo-2-chloropyridine; With n-butyllithium; Triisopropyl borate; In diethyl ether; at -78 - 20 ℃;

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

DOI:10.1016/S0040-4020(02)00152-7

Reference yield: 20.0%

2,5 dichloropyridine (16110-09-1) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 2-chloro-5-(4,4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (444120-94-9)

Guidance literature:

2,5 dichloropyridine; With n-butyllithium; Triisopropyl borate; In diethyl ether; at -78 - 20 ℃;

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

DOI:10.1016/S0040-4020(02)00152-7

upstream raw materials:

2,5 dichloropyridine

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

5-bromo-2-chloropyridine

2-choro-5-iodopyridine

Downstream raw materials:

6-chloropyridine-3-ol

C₁₆H₂₂⁽²⁾HBClNO₄

(R)-1-methyl-4-(phenylsulfinyl)benzene

C₁₆H₂₃BClNO₄

Refernces

• 1、 -. "Nitrogen-containing heterocyclic derivative and organic electroluminescent device thereof". Paragraph 0154-0157. . Retrieved 2021/11/26.
• 2、 Sadler, Scott A.,Tajuddin, Hazmi,Mkhalid, Ibraheem A. I.,Batsanov, Andrei S.,Albesa-Jove, David,Cheung, Man Sing,Maxwell, Aoife C.,Shukla, Lena,Roberts, Bryan,Blakemore, David C.,Lin, Zhenyang,Marder, Todd B.,Steel, Patrick G.. "Iridium-catalyzed C-H borylation of pyridines". supporting information. p. 7318 - 7327. Retrieved 2014/11/07.