55270-33-2

Basic information

• Product Name: 4-IODOISOQUINOLINE
• Synonyms: 4-IODOISOQUINOLINE
• CAS NO: 55270-33-2
• Molecular Formula: C₉H₆IN
• Molecular Weight: 255.06
• Mol File: 55270-33-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 93-94 °C
• Boiling Point: 336.8±15.0 °C(Predicted)
• Appearance: /
• Density: 1.837
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.49±0.10(Predicted)
• CAS DataBase Reference: 4-IODOISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-IODOISOQUINOLINE(55270-33-2)
• EPA Substance Registry System: 4-IODOISOQUINOLINE(55270-33-2)

Safety Data

• Hazardous Substances Data: 55270-33-2(Hazardous Substances Data)

Usage

General Description

4-Iodoisoquinoline is a chemical compound with the molecular formula C9H6IN. It is a halogenated isoquinoline derivative, which is a nitrogen-containing heterocyclic compound. 4-Iodoisoquinoline is used as a building block in organic synthesis, particularly in the pharmaceutical industry for the preparation of various drug molecules. It is known for its wide range of biological activities, including anticancer, antimalarial, and antibacterial properties. The presence of the iodine atom in the molecule gives it unique reactivity and selectivity in chemical reactions, making it a valuable tool in the development of new compounds for medicinal applications.

Upstream product

• 119-65-3 isoquinoline 
• 620-05-3 iodomethylbenzene 
• 15787-39-0 2-benzylisoquinolin-2-ium iodide 
• 685103-98-4 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline 
• 1532-97-4 4-bromoisoquinoline 

Downstream Products

• 119-65-3 isoquinoline 
• 23715-85-7 isoquinolinium 
• 86549-28-2 4-((trimethylsilyl)ethynyl)isoquinoline 
• 19079-89-1 (E)-4-(styryl)isoquinoline 
• 80998-99-8 (Z)-4-styrylisoquinoline 
• 19571-30-3 4-phenylisoquinoline 

Relevant articles and documents

Diastereomers of a cofacial ternaphthalene and two azaternaphthalenes. Syntheses and barriers to isomerization

The title compounds, a mixture of anti and syn diastereomers, were prepared by Pd-catalyzed coupling of areneboronic acids with hetaryl halides. Energy barriers for the interconversion of the diastereomers obtained by kinetic and computational studies show a dependence on the location of the annular nitrogen atom, the ortho providing a smaller barrier than the meta nitrogen atom.

Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts

The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.

I2/TBHP mediated multiple C[sbnd]H bonds functionalization of azaarenes with methylarenes to synthesize iodoisoquinolinones via iodination/N-benzylation/amidation sequence

An oxidative multi-functionalization of azaarenes with benzylic C[sbnd]H bonds of methylarenes via iodination/N-benzylation/amidation cascade, to produce N-benzyl-4-iodoisoquinolin-1(2H)-ones and N-benzyl-3-iodoquinolin-2(1H)-ones is developed. The molecular iodine plays a triple role in activating benzylic sp3 C[sbnd]H bond of methylbenzenes, accelerating the oxidation process and serving as iodination reagent. This reaction utilizes cheap and readily available azaarenes and methylarenes as starting materials and proceeds under metal-free conditions to construct C-I, C[sbnd]N and C[dbnd]O bonds consecutively and afford iodo(iso)quinolinones efficiently.