4-Chloro-2-phenylpyridine

Base Information

• Chemical Name: 4-Chloro-2-phenylpyridine
• CAS No.: 57311-18-9
• Molecular Formula: C11H8ClN
• Molecular Weight: 189.644
• DSSTox Substance ID: DTXSID10376506
• Nikkaji Number: J2.449.937E
• Wikidata: Q72457470
• Mol file: 57311-18-9.mol

Synonyms:4-chloro-2-phenylpyridine;57311-18-9;2-phenyl-4-chloropyridine;Pyridine,4-chloro-2-phenyl-;2-phenyl-4-chloro-pyridine;SCHEMBL1662224;DTXSID10376506;BFRWDRFLYBYSFX-UHFFFAOYSA-N;MFCD04114166;AKOS006291855;SB54011;AS-58563;CS-0059905;FT-0692447;W17819;A1-07861

Chemical Property of 4-Chloro-2-phenylpyridine

Chemical Property:

• Vapor Pressure: 0.00252mmHg at 25°C
• Refractive Index: 1.588
• Boiling Point: 296.5 °C at 760 mmHg
• PKA: 3.00±0.10(Predicted)
• Flash Point: 161.2 °C
• PSA: 12.89000
• Density: 1.186 g/cm³
• LogP: 3.40200
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 189.0345270
• Heavy Atom Count: 13
• Complexity: 154

Purity/Quality:

98%Min ^*data from raw suppliers

4-Chloro-2-phenylpyridine 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC=CC(=C2)Cl
• Description: 4-CHLORO-2-PHENYLPYRIDINE is a derivative of 2-phenylpyrideine. It can be used as an organic intermediate. It is useful during the manufacturing of the organic light emitting diodes (OLEDs).

Technology Process of 4-Chloro-2-phenylpyridine

There total 20 articles about 4-Chloro-2-phenylpyridine 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: 94.0%

2-bromo-4-chloropyridine (22918-01-0) + phenylboronic acid (98-80-6) → 4-chloro-2-phenyl-pyridine (57311-18-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In ethanol; at 100 ℃; for 15h; Inert atmosphere;

DOI:10.1039/c7ob01192j

Reference yield: 92.0%

2,4-dichloropyridine (26452-80-2) + phenylboronic acid (98-80-6) → 4-chloro-2-phenyl-pyridine (57311-18-9) + 2-chloro-4-(phenyl)pyridine (42260-39-9)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate; In 1,4-dioxane; water; at 70 ℃; for 20h; Inert atmosphere;

DOI:10.1021/jo401096u

Reference yield: 91.0%

2,4-dichloropyridine (26452-80-2) + triphenylbismuthane (603-33-8) → 4-chloro-2-phenyl-pyridine (57311-18-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In N,N-dimethyl acetamide; at 90 ℃; for 4h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.tet.2014.11.036

upstream raw materials:

2-phenylpyridin N-oxide

4-chloropyridine N-oxide

phenylmagnesium chloride

2,4-dichloropyridine

Downstream raw materials:

4-(2-Phenylpyridin-4-yl)oxyaniline

4-(4-nitrophenoxy)-2-phenylpyridine

C₄₀H₃₀IrN₃

2-(2-phenylpyridin-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Refernces

• 1、 Ghiazza, Clément,Faber, Teresa,Gómez-Palomino, Alejandro,Cornella, Josep. "Deaminative chlorination of aminoheterocycles". . p. 78 - 84. Retrieved 2021/12/23.
• 2、 Chen, Jing,Ding, Yechun,He, Chen,Hu, Xin,Huang, Qitong,Kuang, Ying,Liu, Jinbiao,Yang, Min. "Palladium-catalyzed c-4 selective coupling of 2,4-dichloropyridines and synthesis of pyridine-based dyes for live-cell imaging". . p. 6498 - 6508. Retrieved 2020/06/09.