3-Iodoquinoline

Base Information

• Chemical Name: 3-Iodoquinoline
• CAS No.: 79476-07-6
• Molecular Formula: C9H6IN
• Molecular Weight: 255.058
• European Community (EC) Number: 850-284-2
• DSSTox Substance ID: DTXSID00460241
• Nikkaji Number: J1.186.132F
• Mol file: 79476-07-6.mol

Synonyms:3-iodoquinoline;79476-07-6;MFCD11656390;Quinoline, 3-iodo-;SCHEMBL372216;DTXSID00460241;NDQXBRCPYKGVED-UHFFFAOYSA-N;AMY25861;AB9519;ZB0115;AKOS016012435;SB72039;AS-44973;SY191981;CS-0103668;FT-0749064;EN300-75393;Z1172379319

Chemical Property of 3-Iodoquinoline

Chemical Property:

• Melting Point: 61.5-62.5 °C
• Boiling Point: 105-107 °C(Press: 0.25 Torr)
• PKA: 2.89±0.11(Predicted)
• PSA: 12.89000
• Density: 1.837±0.06 g/cm3(Predicted)
• LogP: 2.83940
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 254.95450
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

98%, ^*data from raw suppliers

3-Iodoquinoline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C=N2)I
• General Description: 3-IODOQUINOLINE is a halogenated quinoline derivative synthesized via a regioselective, metal-free iodocyclization of 2-tosylaminophenylprop-1-yn-3-ols using molecular iodine, yielding 3-IODOQUINOLINE efficiently (up to 99%) under mild and environmentally friendly conditions. This method provides a practical route to access 3-iodoquinolines, which are valuable intermediates for further functionalization due to their pharmacological relevance.

Technology Process of 3-Iodoquinoline

There total 9 articles about 3-Iodoquinoline 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: 100.0%

3-bromoquinoline (5332-24-1) → 3-Iodoquinoline (79476-07-6)

Guidance literature:

With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 110 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2010.11.008

Reference yield: 97.0%

→ 3-Iodoquinoline (79476-07-6)

Guidance literature:

Reference yield: 96.0%

3-(trimethylstannyl)quinoline (79476-05-4) → 3-Iodoquinoline (79476-07-6)

Guidance literature:

With iodine; In chloroform; for 0.25h; Ambient temperature;

upstream raw materials:

3-aminoquinoline

3-bromoquinoline

3-(trimethylstannyl)quinoline

quinoline

Downstream raw materials:

3-phenylquinoline

3-phenylsulfanyl-quinoline

3-<(E)-2-phenylethenyl>-quinoline

3-methylquinoline

Refernces

Electrophile-driven regioselective synthesis of functionalized quinolines

10.1021/ol2007154

The research focuses on the development of an efficient and highly regioselective method for synthesizing substituted quinolines, which are important heterocyclic compounds with various pharmacological properties. The study aims to overcome the limitations of classical syntheses that often require harsh conditions and are incompatible with sensitive substrates. The researchers utilized 2-tosylaminophenylprop-1-yn-3-ols as starting materials and molecular iodine (I2) to achieve a 6-endo-dig iodocyclization, resulting in the formation of 3-iodoquinolines with moderate to excellent yields (up to 99%). The process is metal-free, environmentally benign, and offers a significant advancement in the synthesis of quinolines.

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