2-Chloro-3-iodopyridine

Base Information

• Chemical Name: 2-Chloro-3-iodopyridine
• CAS No.: 78607-36-0
• Molecular Formula: C5H3ClIN
• Molecular Weight: 239.443
• Hs Code.: 29333990
• European Community (EC) Number: 675-002-3
• DSSTox Substance ID: DTXSID40370916
• Nikkaji Number: J1.537.712G
• Wikidata: Q72452579
• Mol file: 78607-36-0.mol

Synonyms:2-chloro-3-iodopyridine;78607-36-0;Pyridine, 2-chloro-3-iodo-;2-Chloro-3-iodo-pyridine;MFCD00661298;2-chloro-3- iodopyridine;SCHEMBL165854;2-chloranyl-3-iodanyl-pyridine;2-Chloro-3-iodopyridine, 97%;DTXSID40370916;OHWSWGXNZDSHLM-UHFFFAOYSA-N;BCP03191;CS-D0940;GEO-02627;STK688514;AKOS005137882;AB06631;AC-1103;PS-7596;BP-10801;SY004388;A9873;AM20061506;C2193;FT-0641685;EN300-93247;A809376;AJ-333/25006075;Q-103361

Chemical Property of 2-Chloro-3-iodopyridine

Chemical Property:

• Appearance/Colour: Off-white crystal
• Vapor Pressure: 0.019mmHg at 25°C
• Melting Point: 93-96 °C
• Refractive Index: 1.642
• Boiling Point: 261.2 °C at 760 mmHg
• PKA: -0.70±0.10(Predicted)
• Flash Point: 111.8 °C
• PSA: 12.89000
• Density: 2.052 g/cm³
• LogP: 2.33960
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 238.89987
• Heavy Atom Count: 8
• Complexity: 78.8

Purity/Quality:

99% ^*data from raw suppliers

2-Chloro-3-iodopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/22-41-22
• Safety Statements: 36/37/39-26-22-36-39-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(N=C1)Cl)I
• General Description: 2-Chloro-3-iodopyridine is a key intermediate in the synthesis of imidazo[4,5-b]pyridin-2-ones, serving as a versatile starting material for regioselective palladium-catalyzed amination reactions. Its reactivity allows for sequential functionalization, enabling efficient access to pharmacologically relevant heterocycles with diverse substituents. The compound’s utility lies in its ability to undergo mild, functional group-tolerant transformations, facilitating the rapid construction of complex structures not easily attainable by conventional methods.

Technology Process of 2-Chloro-3-iodopyridine

There total 4 articles about 2-Chloro-3-iodopyridine 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: 67.0%

2-chloropyridine (109-09-1) → 2-chloro-4-iodopyridine (153034-86-7) + 2-chloro-3-iodopyridine (78607-36-0)

Guidance literature:

2-chloropyridine; With Bu(TMP)2MgLi; In diethyl ether; at -10 ℃; for 2h;

With iodine; In diethyl ether; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.08.151

Reference yield:

2-chloropyridine (109-09-1) → 2-chloro-4-iodopyridine (153034-86-7) + 2-chloro-3,6-diiodopyridine + 2-chloro-3-iodopyridine (78607-36-0) + 2-chloro-5-iodo-pyridine (258506-66-0)

Guidance literature:

2-chloropyridine; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; ZnCl₂-N,N,N’,N’-tetramethylethylenediamine; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

With iodine; In tetrahydrofuran; regioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201101993

Reference yield:

2-chloropyridine (109-09-1) → 2-chloro-4-iodopyridine (153034-86-7) + 2,5-di-iodopyridine (116195-81-4) + 2-chloro-3,6-diiodopyridine + 2-chloro-3-iodopyridine (78607-36-0) + 2-chloro-5-iodo-pyridine (258506-66-0)

Guidance literature:

2-chloropyridine; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; ZnCl₂-N,N,N’,N’-tetramethylethylenediamine; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

With iodine; In tetrahydrofuran; regioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201101993

upstream raw materials:

2-chloropyridine

Downstream raw materials:

1-(3-iodopyridin-2-yl)piperazine

2,2-dimethyl-N-(2-(2-chloro-3-pyridyl)phenyl)propanamide

2-chloro-4-iodopyridine

3-iodo-2-aminopyridine

Refernces

Synthesis of disubstituted imidazo[4,5-b]pyridin-2-ones

10.1021/jo048887v

Imidazo[4,5-b]pyridin-2-ones, which are pharmaceutically important heterocyclic compounds with various biological activities. The authors utilized a sequential palladium-catalyzed coupling protocol involving key chemicals such as 2-chloro-3-iodopyridine as the starting material, palladium acetate and BINAP as catalysts, cesium carbonate and sodium tert-butoxide as bases, and anilines as coupling partners. The process includes a regioselective palladium-catalyzed amination of 2-chloro-3-iodopyridine to form aminopyridines, followed by another amination to produce diaminopyridines, and finally cyclization with triphosgene to yield the target imidazo[4,5-b]pyridin-2-ones. The method is mild, tolerant of a wide range of functional groups, and allows for the preparation of novel heterocycles in just two or three synthetic steps, which are not accessible through current synthetic methods. The research concludes that this approach provides a versatile and efficient route to synthesize these pharmaceutically interesting compounds, offering rapid access to highly functionalized derivatives.