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

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

Uses

Used in Chemical Reactions and Organic Synthesis:
1-Iodoisoquinoline is used as a versatile building block for the synthesis of pharmaceuticals and other biologically active compounds. Its presence in various chemical reactions contributes to the creation of a wide array of organic molecules with potential applications in different fields.
Used in Pharmaceutical Preparation:
1-Iodoisoquinoline is utilized as a key intermediate in the preparation of pharmaceuticals, owing to its ability to facilitate the development of new drugs with enhanced therapeutic properties.
Used in the Development of New Materials:
1-IODOISOQUINOLINE is also investigated for its potential use in the development of new materials, where its unique characteristics can contribute to the advancement of various industries.
Used as a Reagent in Organometallic Chemistry:
1-Iodoisoquinoline serves as a reagent in organometallic chemistry, where its reactivity and structural attributes are harnessed to achieve specific chemical transformations and syntheses.

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

Downstream Products

• 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 
• 1432725-53-5 (2-bromo-5-trifluoromethylphenyl)isoquinolin-1-ylacetonitrile 
• 7661-40-7 1-isobutylisoquinoline 
• 3297-72-1 1-phenylisoquinoline 
• 134948-99-5 1-(3'-methoxy)phenylisoquinoline 
• 855532-95-5 1-(3'-methyl)phenylisoquinoline 
• 42088-41-5 1-(methylthio)isoquinoline 
• 13033-04-0 1-phenethylisoquinoline 
• 5467-92-5 isoquinolin-1-yl(diphenyl)methanol 
• 7661-38-3 1-butylisoquinoline 

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

Lipshutz-type bis(amido)argentates for directed: Ortho argentation

Bis(amido)argentate (TMP)2Ag(CN)Li2 (3, TMP-Ag-ate; TMP = 2,2,6,6-tetramethylpiperidido) was designed as a tool for chemoselective aromatic functionalization via unprecedented directed ortho argentation (DoAg). X-Ray crystallographic analysis showed that 3 takes a structure analogous to that of the corresponding Lipshutz cuprate. DoAg with this TMP-Ag-ate afforded multifunctional aromatics in high yields in processes that exhibited high chemoselectivity and compatibility with a wide range of functional groups. These included organometallics- A nd transition metal-susceptible substituents such as methyl ester, aldehyde, vinyl, iodo, (trifluoromethanesulfonyl)oxy and nitro groups. The arylargentates displayed good reactivity with various electrophiles. Chalcogen (S, Se, and Te) installation and azo coupling reactions also proceeded efficiently.

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.

Direct conversion of 1-(2-bromobenzoyl)isoquinolines to dibenzo[ de,g ]quinolin-7-ones via reductive photocyclization

A series of A/D-ring substituted dibenzo[de,g]quinolin-7-ones was produced from the corresponding isoquinolinones and (2-bromophenyl)acetonitriles in four steps. This represents a convenient approach toward the synthesis of tetracyclic alkaloids. A direct conversion of 1-(2-bromobenzoyl)isoquinolines to dibenzo[de,g]quinolin-7-ones is the key step in the total synthesis. The yield of the reductive photocyclization depends on the position of the substituents at the isoquinolyl ring and the phenyl group. The mechanism of the reductive photocyclization is also discussed.

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

Preparation of polyfunctional zinc organometallics using an Fe- or Co-catalyzed Cl/Zn-exchange

A new Fe- or Co-catalyzed Cl/Zn-exchange reaction allows the direct transformation of aryl, heteroaryl, and also alkyl chlorides into the corresponding zinc reagents. The method tolerates functional groups such as a nitrile or an ester. Remarkably, secondary and tertiary alkyl chlorides are suitable substrates for the Cl/Zn exchange.

Scaleable preparation of functionalized organometallics via directed ortho metalation using Mg- and Zn-amide bases

A range of aryl and heteroaryl organometallics are efficiently prepared in THF Wia directed ortho metalation by using the previously reported amide bases tmpMgCl · LiCl (tmp ) 2,2,6,6-tetramethylpiperidyl), tmp2Mg · 2LiCl and tmp2Zn

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

Microwave-assisted trans-halogenation reactions of various chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines, isoquinolines, and pyridines leading to the corresponding iodinated heterocycles

(Chemical Equation Presented) Microwave irradiation of certain chloro-, bromo-, trifluoromethanesulfonyloxy- and nonafluorobutanesulfonyloxy-substituted quinolines in the presence of acetic anhydride and sodium iodide leads, via a trans-halogenation process, to the corresponding iodides in high yield. Related conversions involving pyridines and isoquinolines can also be achieved under similar conditions.

Controlling axial conformation in 2-Arylpyridines and 1-Arylisoquinolines: Application to the asymmetric synthesis of QUINAP by dynamic thermodynamic resolution

Unlike related biphenyl compounds, 2-arylpyridines and 1-arylisoquinolines can be induced to adopt preferentially one of two axial conformationsby the presence of a sulfinyl substituent adjacent to the Ar-Ar bond. I n the case of more substituted biaryls,