244221-57-6

Basic information

• Product Name: 5-CHLORO-2-IODOPYRIDINE
• Synonyms: 5-CHLORO-2-IODOPYRIDINE;2-IODO-5-CHLOROPYRIDINE
• CAS NO: 244221-57-6
• Molecular Formula: C₅H₃ClIN
• Molecular Weight: 239.44
• EINECS: 1308068-626-2
• Product Categories: Pyridine;Pyridine Series;Pyrimidine Series;Pyridines;Heterocycle-Pyridine series;organic building block
• Mol File: 244221-57-6.mol

Chemical Properties

• Melting Point: 85-87 °C(Solv: hexane (110-54-3))
• Boiling Point: 237.263 °C at 760 mmHg
• Flash Point: 97.293 °C
• Appearance: /Solid
• Density: 2.052 g/cm³
• Vapor Pressure: 0.03mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -0.44±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Light Sensitive
• CAS DataBase Reference: 5-CHLORO-2-IODOPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2-IODOPYRIDINE(244221-57-6)
• EPA Substance Registry System: 5-CHLORO-2-IODOPYRIDINE(244221-57-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Hazardous Substances Data: 244221-57-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-2-IODOPYRIDINE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structural features make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5-CHLORO-2-IODOPYRIDINE is used as a starting material for the preparation of indolizines through a tandem palladium-catalyzed cross-coupling reaction and cycloisomerization. This process allows for the efficient synthesis of indolizines, which are important structural motifs in various biologically active compounds.
Used in Medicinal Chemistry:
5-CHLORO-2-IODOPYRIDINE is also utilized in the synthesis and structure-activity relationships of 2-aminoquinazoline derivatives. These derivatives have been identified as a novel class of metabotropic glutamate receptor 5 (mGlu5) negative allosteric modulators. mGlu5 is a target for various therapeutic applications, including the treatment of neurological disorders and cognitive impairments. The development of selective and potent mGlu5 negative allosteric modulators can lead to new therapeutic options for these conditions.

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

Upstream product

• 16110-09-1 2,5 dichloropyridine 
• 40473-01-6 2-Bromo-5-chloro-pyridine 
• 75-36-5 acetyl chloride 
• 87412-10-0 5-chloro-2-<<(trifluoromethyl)sulfonyl>oxy>pyridine 
• 52132-34-0 2-amino-5-chloro-N-oxide pyridine 

Downstream Products

• 327056-55-3 5-chloro-N'-hydroxypyridine-2-carboximidamide 
• 823221-96-1 2-iodo-3-chloro-6-(trifluoromethyl)pyridine 
• 823221-95-0 5-chloro-4-iodo-2-(trifluoromethyl)pyridine 
• 823222-01-1 5-chloro-2-(trifluoromethyl)pyridine-4-carboxylic acid 
• 31181-89-2 5-chloro-2-pyridine carboxaldehyde 
• 89809-64-3 2-cyano-5-chloropyridine 
• 1243715-39-0 6-chloro-1-ethoxycarbonyl-3-methylindolizine 
• 1243715-40-3 6-chloro-1-ethoxycarbonyl-3-ethylindolizine 
• 1320343-77-8 C₂₄H₂₃FN₄O 
• 1214333-69-3 3-chloro-6-(trifluoromethyl)picolinonitrile 
• 1393823-04-5 5-(5-chloropyridin-2-yl)-2-(1,3-dioxolan-2-yl)pyridine 

Relevant articles and documents

A New, Simple, and General Synthesis of N -Oxides of Iodopyridines and Iodoquinolines via the Diazotization-Iodination of Heterocyclic Amino N -Oxides in the Presence of p -Toluenesulfonic Acid in Water

The diazotization of a series of N -oxides of aminopyridines and aminoquinolines under the action of sodium nitrite in the presence of KI and p -TsOH in water at room temperature leads to the formation of the corresponding N -oxides of iodopyridines and iodoquinolines in high yields. The method has a general character and can be used for the preparation of 3-, 2-, and 4- N -oxides of iodopyridines.

CYCLOHEXYL-AZETIDINYL ANTAGONISTS OF CCR2

The present invention comprises compounds of Formula (I). wherein: R1, R2, X, and Z are as defined in the specification. The invention also comprises a method of preventing, treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is type II diabetes, obesity and asthma. The invention also comprises a method of inhibiting CCR2 activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula (I).

One-pot iodination of hydroxypyridines

(Chemical Equation Presented) A one-pot, high-yielding iodination of hydroxypyridines and hydroxyquinolines is described. The iodination proceeds under mild conditions, and the products are obtained in high yield without the need for chromatographic purif

MELANOCORTIN TYPE 4 RECEPTOR AGONIST PIPERIDINOYLPYRROLIDINES

The present invention relates to a class of melanocortin MCR4 agonists of general formula (I), wherein the variables and substituents are as defined herein and especially to selective MCR4 agonist compounds, to their use in medicine, particularly in the treatment of sexual dysfunction and obesity, to intermediates useful in their synthesis and to compositions containing them.

PIPERIDINOYL-PYRROLIDINE AND PIPERIDINOYL-PIPERIDINE COMPOUNDS

The present invention relates to a class of compounds of general formula (I) and the salts, hydrates, solvates, polymorphs and prodrugs wherein n, R6, R7 and R10 are as defined herein and especially to MCR4 agonist compounds of formula (I), to their use in medicine, particularly in the treatment of sexual dysfunction and obesity, to intermediates useful in their synthesis and to compositions containing them.

Discovery and structure-activity relationship of 3-aryl-5-aryl-1,2,4- oxadiazoles as a new series of apoptosis inducers and potential anticancer agents

We have identified 5-(3-chlorothiophen-2-yl)-3-(4-trifluoromethylphenyl)-1, 2,4-oxadiazole (1d) as a novel apoptosis inducer through our caspase- and cell-based high-throughput screening assay. Compound 1d has good activity against several breast and colorectal cancer cell lines but is inactive against several other cancer cell lines. In a flow cytometry assay, treatment of T47D cells with 1d resulted in arrest of cells in the G1 phase, followed by induction of apoptosis. SAR studies of Id showed that the 3-phenyl group can be replaced by a pyridyl group, and a substituted five-member ring in the 5-position is important for activity. 5-(3-Chlorothiophen-2-yl)-3-(5- chloropyridin-2-yl)-1,2,4-oxadiazole (41) has been found to have in vivo activity in a MX-1 tumor model. Using a photoaffinity agent, the molecular target has been identified as TIP47, an IGFII receptor binding protein. Therefore, our cell-based chemical genetics approach for the discovery of apoptosis inducers can identify potential anticancer agents as well as their molecular targets.

Logistic flexibility in the preparation of isomeric halopyridinecarboxylic acids

Although there are many conceivable ways to funtionalize, and specifically carboxylate, 2-chloro-4-(trifluoromethyl)pyridine optionally at all three vacant positions, it is more straightforward to prepare only the 2-chloro-4- (trifluoromethyl)pyridine-3-carboxylic acid (1) from this precursor and the other 6-chloro-4-(trifluoromethyl)pyridine-2- and -3-carboxylic acids (2 and 3) from a different one, viz. 5-bromo-2-chloro-4-(trifluoromethyl)pyridine. In the same manner, it proved more convenient to convert 5-chloro-2-(trifluoromethyl) pyridine in only two of the corresponding acids (6 and 7) and to make the third one (8) from 3-bromo-5-chloro-2-(trifluoromethyl)pyridine as an alternative starting material. All model substrates for functionalization were readily accessible from the correspondingly substituted chloroiodopyridine through heavy halogen displacement by in situ generated (trifluoromethyl)copper. Graphical Abstract

Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof

The present invention is directed to substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs thereof, represented by the Formula I: wherein Ar1, Ar3, A, B and D are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

Silyl-mediated halogen/halogen displacement in pyridines and other heterocycles

Heating with bromotrimethylsilane converts 2-chloropyridine into 2-bromopyridine and 2-chloro-6-methylpyridine into 2-bromo-6-methylpyridine. Both 2-chloropyridines and 2-bromopyridines give the corresponding iodo compound when treated with in situ generated iodotrimethylsilane. Although 3- and 4-chloropyridine are completely inert, 2,4-dichloropyridine undergoes the halogen/halogen exchange simultaneously at the 2- and 4-position. Halogen displacement takes place exclusively at the 2-position with 2,3-dichloropyridine and 2,5-dichloropyridine. In agreement with the intermediacy of N-trimethylsilylpyridinium salts as a prerequisite for the occurrence of halogen exchange, neither 2-fluoropyridine and 2-fluoro-6-methylpyridine nor any 2,6-dihalopyridine reacts. Finally, bromine/chlorine and iodine/chlorine substitution can also be accomplished with 2-or 4-chloroquinoline, 1-chloroisoquinoline, 2-chloropyrimidine, chloropyrazine and 2,3-dichloroquinoxaline as substrates. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).