153034-86-7

Basic information

• Product Name: 2-Chloro-4-iodopyridine
• Synonyms: 2-CHLORO-IODOPYRIDINE;2-CHLORO-4-IODOPYRIDINE;4-Iodo-2-chloropyridine;2-CHLORO-4-IODOPYRIDINE,99%;2-Chloro-4-iodopyridine,98%;2-Chloro-4-iodopyrid;2-Chloro-4-iodopyridine, 98% 1GR;Pyridine, 2-chloro-4-iodo-
• CAS NO: 153034-86-7
• Molecular Formula: C₅H₃ClIN
• Molecular Weight: 239.44
• EINECS: -0
• Product Categories: Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Halides;Pyridines;Halogenated;Organohalides;Chloropyridines;Halopyridines;Iodopyridines;Bases & Related Reagents;Nucleotides;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Propidium heterocyclic series;Miscellaneous Reagents;alkyl Iodine| alkyl chloride
• Mol File: 153034-86-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 42-43 °C(lit.)
• Boiling Point: 255.5 °C at 760 mmHg
• Flash Point: 110 °C
• Appearance: White to yellow/Crystals or Crystalline Flakes
• Density: 2.052 g/cm³
• Vapor Pressure: 0.026mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate
• PKA: -0.03±0.10(Predicted)
• Sensitive: Light Sensitive
• BRN: 108668
• CAS DataBase Reference: 2-Chloro-4-iodopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-iodopyridine(153034-86-7)
• EPA Substance Registry System: 2-Chloro-4-iodopyridine(153034-86-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-41-43-36/37/38-20/22
• Safety Statements: 26-36/37/39-36-22
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 153034-86-7(Hazardous Substances Data)

Usage

Description

2-Chloro-4-iodopyridine, with the CAS number 153034-86-7, is an organic compound characterized by its off-white crystalline appearance. It is a derivative of pyridine, a heterocyclic compound with a nitrogen atom in the ring structure, and features a chlorine atom at the 2nd position and an iodine atom at the 4th position. 2-Chloro-4-iodopyridine is known for its utility in various chemical reactions and processes.

Uses

Used in Organic Synthesis:
2-Chloro-4-iodopyridine is used as a synthetic building block for the creation of more complex organic molecules. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable compound in the field of organic chemistry. The presence of both a chlorine and an iodine atom in the molecule provides opportunities for further functionalization and modification, which can be exploited to synthesize a variety of target molecules with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-4-iodopyridine is used as an intermediate in the synthesis of various drugs and drug candidates. Its reactivity and structural diversity make it a suitable starting material for the development of new therapeutic agents. The compound can be further modified to introduce different functional groups, which can enhance the biological activity and pharmacological properties of the resulting drug molecules.
Used in Chemical Research:
2-Chloro-4-iodopyridine is also utilized in academic and industrial research settings for the investigation of novel chemical reactions and mechanisms. Its unique structural features make it an interesting subject for study, and researchers can use it to explore new synthetic routes, reaction conditions, and catalysts. The insights gained from these studies can contribute to the advancement of chemical science and the development of new technologies and applications.

InChI:InChI=1/C5H3ClIN/c6-5-3-4(7)1-2-8-5/h1-3H

Upstream product

• 14432-12-3 4-Amino-2-chloropyridine 
• 78607-36-0 2-chloro-3-iodopyridine 
• 109-09-1 2-chloropyridine 
• 2402-95-1 2-chloropyridine-N-oxide 
• 14432-16-7 2-chloro-4-nitropyridine-N-oxide 
• 65287-34-5 2-chloropyridine-4-carbonyl chloride 
• 6313-54-8 2-chloroisonicotinic acid, 

Downstream Products

• 219727-28-3 4-allyl-2-chloropyridine 
• 26452-80-2 2,4-dichloropyridine 
• 81565-18-6 2-chloro-4-trifluoromethyl pyridine 
• 700811-29-6 (2-chloropyridin-4-yl)hydrazine 
• 73027-79-9 4,6-dichloro-nicotinic acid 
• 343781-36-2 2,4-dichloro-3-iodo-pyridine 
• 343781-49-7 2,4-dichloro-5-iodopyridine 
• 262423-77-8 2,4-dichloronicotinic acid 
• 499193-57-6 2-chloro-4-[(trimethylsilyl)ethynyl]pyridine 

Relevant articles and documents

Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange

We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.

Concise Entries to 4-Halo-2-pyridones and 3-Bromo-4-halo-2-pyridones

Methods for the synthesis of both simple 4-halo-2-pyridones and more functionalized 3,4-di- and (3,4,5-tri)-halo-2-pyridones are described that are based on a combination of Sandmeyer and regioselective (copper-mediated) halogenation, with a 2-chloro or a 2-benzyloxy moiety serving as a masked 2-pyridone.

Deprotonative metalation of chloro- and bromopyridines using amido-based bimetallic species and regioselectivity-computed CH acidity relationships

A series of chloro- and bromopyridines have been deprotometalated by using a range of 2,2,6,6-tetramethylpiperidino-based mixed lithium-metal combinations. Whereas lithium-zinc and lithium-cadmium bases afforded different mono- and diiodides after subsequent interception with iodine, complete regioselectivities were observed with the corresponding lithium-copper combination, as demonstrated by subsequent trapping with benzoyl chlorides. The obtained selectivities have been discussed in light of the CH acidities of the substrates, determined both in the gas phase and as a solution in THF by using the DFT B3LYP method.