19658-77-6

Basic information

• Product Name: 1-IODOISOQUINOLINE
• Synonyms: 1-IODOISOQUINOLINE
• CAS NO: 19658-77-6
• Molecular Formula: C₉H₆IN
• Molecular Weight: 255.06
• Product Categories: Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Isoquinolines
• Mol File: 19658-77-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 72-76℃
• Boiling Point: 336.8°C at 760 mmHg
• Flash Point: 157.5°C
• Appearance: /
• Density: 1.837g/cm³
• Vapor Pressure: 0.000214mmHg at 25°C
• Refractive Index: 1.724
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: soluble in Methanol
• PKA: 2.27±0.30(Predicted)
• CAS DataBase Reference: 1-IODOISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-IODOISOQUINOLINE(19658-77-6)
• EPA Substance Registry System: 1-IODOISOQUINOLINE(19658-77-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 19658-77-6(Hazardous Substances Data)

Usage

General Description

1-Iodoisoquinoline is a chemical compound with the molecular formula C9H6IN. It is a derivative of isoquinoline and contains a iodine atom attached to the 1-position of the isoquinoline ring. 1-IODOISOQUINOLINE is used in various chemical reactions and organic synthesis processes. It is a versatile building block for the preparation of pharmaceuticals and other biologically active compounds. 1-Iodoisoquinoline has also been investigated for its potential use in the development of new materials and as a reagent in organometallic chemistry. Its unique structure and reactivity make it a valuable tool in the field of medicinal and organic chemistry.

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

Upstream product

• 19493-44-8 1-chloroisoquinoline 
• 119-65-3 isoquinoline 
• 1161941-05-4 isoquinolin-1-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 123172-86-1 1-(trifluoromethanesulfonyloxy)isoquinoline 
• 491-30-5 1-hydroxyisoquinoline 
• 491-30-5 1-isoquinolone 
• 7468-67-9 o-formylbenzonitrile 

Downstream Products

• 119-65-3 isoquinoline 
• 17999-93-8 1,1'-Biisoquinoline 
• 46502-61-8 ethyl 2-(isoquinolin-1-yl)acetate 
• 140458-75-9 1-[2-(Diphenyl-phosphinoyl)-3,6-dimethoxy-phenyl]-isoquinoline 
• 86521-10-0 1-(trimethylsilylethynyl)isoquinoline 
• 16576-23-1 1-benzoylisoquinoline 
• 86520-96-9 1-ethynylisoquinoline 
• 380427-61-2 1-(2-bromo-phenyl)isoquinoline 
• 394-65-0 1-fluoroisoquinoline 
• 1383571-57-0 (2-bromophenyl)(isoquinolin-1-yl)methanone 
• 10134-02-8 (2-bromo-4,5-dimethoxyphenyl)isoquinolin-1-ylmethanone 
• 38750-39-9 7H-dibenzo[de,g]quinolin-7-one 
• 101439-09-2 (2-bromophenyl)isoquinolin-1-yl-acetonitrile 
• 1432725-51-3 (2-bromo-4,5-dimethoxyphenyl)isoquinolin-1-yl-acetonitrile 

Relevant articles and documents

Enantioselective Dearomative [3 + 2] Umpolung Annulation of N-Heteroarenes with Alkynes

Enantioselective [3 + 2] annulation of N-heteroarenes with alkynes has been developed via a cobalt-catalyzed dearomative umpolung strategy in the presence of chiral ligand and reducing reagent. A variety of electron-deficient N-heteroarenes, including qui

An Unprecedented, Lewis Acid-Mediated, Metal-Free Iodoannulation Strategy to Aromatic Iodides

A direct transformation of ortho-alkynylated aromatic vinyl ethers to 1-iodonaphthalenes and other iodo-heterocycles under mild Lewis acidic conditions in the presence of iodide as an external nucleophile is reported. The first example of an iodoannulation strategy using a nucleophilic source of iodine, coupled with good to excellent yields, exclusive alpha regioselectivity and a broad substrate scope makes this work an attractive avenue towards the construction of aromatic iodides.

Computed CH acidity of biaryl compounds and their deprotonative metalation by using a mixed lithium/Zinc-TMP base

With the aim of synthesizing biaryl compounds, several aromatic iodides were prepared by the deprotonative metalation of methoxybenzenes, 3-substituted naphthalenes, isoquinoline, and methoxypyridines by using a mixed lithium/zinc-TMP (TMP=2,2,6,6-tetramethylpiperidino) base and subsequent iodolysis. The halides thus obtained, as well as commercial compounds, were cross-coupled under palladium catalysis (e.g., Suzuki coupling with 2,4-dimethoxy-5-pyrimidylboronic acid) to afford various representative biaryl compounds. Deprotometalation of the latter compounds was performed by using the lithium/zinc-TMP base and evaluated by subsequent iodolysis. The outcome of these reactions has been discussed in light of the CH acidities of these substrates, as determined in THF solution by using the DFT B3LYP method. Except for in the presence of decidedly lower pKa values, the regioselectivities of the deprotometalation reactions tend to be governed by nearby coordinating atoms rather than by site acidities. In particular, azine and diazine nitrogen atoms have been shown to be efficient in inducing the reactions with the lithium/zinc-TMP base at adjacent sites (e.g., by using 1-(2-methoxyphenyl)isoquinoline, 4-(2,5-dimethoxyphenyl)-3-methoxypyridine, or 5-(2,5-dimethoxyphenyl)-2,4-dimethoxypyrimidine as the substrate), a behavior that has already been observed upon treatment with lithium amides under kinetic conditions. Finally, the iodinated biaryl derivatives were involved in palladium-catalyzed reactions. Copyright