16560-43-3

Basic information

• Product Name: 4-IODOQUINOLINE
• Synonyms: 4-IODOQUINOLINE;4-Iodoquinoline 97%;4-Iodoquinoline ,98%;4-Iodo-1-azanaphthalene;4-Iodoquinoline97%
• CAS NO: 16560-43-3
• Molecular Formula: C₉H₆IN
• Molecular Weight: 255.06
• Mol File: 16560-43-3.mol

Chemical Properties

• Melting Point: 98-100
• Boiling Point: 320.7 °C at 760 mmHg
• Flash Point: 147.8 °C
• Appearance: /
• Density: 1.7856 (estimate)
• Vapor Pressure: 0.000585mmHg at 25°C
• Refractive Index: 1.724
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 3.58±0.13(Predicted)
• CAS DataBase Reference: 4-IODOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-IODOQUINOLINE(16560-43-3)
• EPA Substance Registry System: 4-IODOQUINOLINE(16560-43-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 16560-43-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Iodoquinoline is used as a reagent for the synthesis of aryl hydantoin Ro 13-3978, an antischistosomal compound. 4-IODOQUINOLINE is effective against schistosomiasis, a parasitic disease, and is known to produce antiandrogenic side effects.
Additionally, due to its chemical properties and reactivity, 4-Iodoquinoline may have potential applications in other areas of the pharmaceutical industry, such as the development of new drugs or as an intermediate in the synthesis of complex organic molecules. However, further research and development would be required to explore these possibilities.

InChI:InChI=1/C9H6IN/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H

Upstream product

• 3964-04-3 4-bromoquinoline 
• 611-35-8 4-chloroquinoline 
• 79476-06-5 4-trimethylstannyl-quinoline 

Downstream Products

• 91-22-5 quinoline 
• 21280-66-0 4-(thiophen-2-yl)quinoline 
• 4789-81-5 ethyl 4-quinolineacetate 
• 27080-08-6 4-(quinolin-4-yl)quinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 62484-52-0 4-ethynylquinoline 
• 892860-41-2 C₆₂H₈₀N₄O₁₆ 
• 892860-40-1 C₆₁H₇₈N₄O₁₆ 

Relevant articles and documents

Acid-Mediated Halogen Exchange in Heterocyclic Arenes: A Highly Effective Iodination Method

Heterocyclic arenes including pyridyl, quinolyl, and isoquinolyl chlorides have been converted to their corresponding iodides in good to high yields via acid-mediated nucleophilic halogen exchange with sodium iodide. This procedure avoids the use of transition metals, harsh reaction conditions, and affords highly regioselective halide exchange. Chloride substituents in position 2 and 4 of pyridines and quinolines are readily substituted by iodide in 75-91% and conversion of 1-chloroisoquinoline to its iodide derivative was found to proceed with 90% yield. Positions that are not activated for nucleophilic aromatic substitution proved to be inert to halide exchange. Regioselective chloride/iodide exchange in 4,7-dichloroquinoline hydrochloride gave 7-chloro-4-iodoquinoline, an important precursor of anti-malaria drugs, in almost 90% yield.

Tributylmagnesium ate complex-mediated bromine-magnesium exchange of bromoquinolines: A convenient access to functionalized quinolines

2-, 3- and 4-bromoquinolines were converted to the corresponding lithium tri(quinolyl)magnesates at -10°C by treatment with Bu3MgLi in THF or toluene. The resulting organomagnesium derivatives were quenched by various electrophiles to afford functionalized quinolines.

Synthesis and reactivity of lithium tri(quinolinyl)magnesates

2-, 3- and 4-Bromoquinolines were converted to the corresponding lithium tri(quinolinyl)magnesates at -10°C when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines.

Substituted phenyl farnesyltransferase inhibitors

Compounds of formula (I) or pharmaceutically acceptable salts thereof, inhibit farnesyltransferase. Methods for making the compounds, pharmaceutical compositions containing the compounds, and methods of treatment using the compounds are disclosed.

Studies on Organometallic Compounds. II. Facile and Convenient Method for the Synthesis of Idoazines through Iododestannation of Trimethylstannylazines

Trimethylsatannyl and bis(trimethylstannyl) derivatives of pyridine, quinoline, and isoquinoline were prepared from the corresponding halo and dihalo (chloro or bromo) derivatives and trimethylstannyl sodium, which was generated in situ from chlorotrimethylsatannane and sodium.These stannyl derivatives readily underwent iododestannation on treatment with iodine to produce the corresponding iodo and diiodo derivatives of pyridine, quinoline, and isoquinoline, respectively, in good yields.Keywords -trimethylsannylazine; bis(trimethylstannyl)azine; iodoazine; diiodoazine; iododestannation; trimethylstannyl sodium; chlorotrimethylstannane

STANNYLATION-IODINATION REACTION ON PYRIDINE NUCLEI. A FACILE METHOD FOR SYNTHESIS OF IODOPYRIDINES AND IODOQUINOLINES.

Pyridines and quinolines bearing trimethylstannyl substituent at 2-, 3-, or 4-position were synthesized by the reaction of the respective chloro or bromo derivatives with trimethylstannyl sodium, generated in situ from chlorotrimethylstannane and sodium, in the range of 61-88percent yields.Upon treatment with iodine, these trimethylstannyl derivatives smoothly underwent iododemetallation to give the corresponding iodo derivatives of pyridine and quinoline in satisfactory yields.