19493-44-8

Usage

Chemical Description

1-chloroisoquinoline is an organic compound used as a starting material in the synthesis of other compounds.

Uses

1. Used in Chemical Synthesis:
1-Chloroisoquinoline is used as a key intermediate in the synthesis of various organic compounds. Its reactivity with different reagents allows for the formation of a wide range of products, making it a versatile building block in organic chemistry.
2. Used in Pharmaceutical Applications:
1-Chloroisoquinoline is used as a starting material for the development of new pharmaceutical compounds. One such application is in the preparation of aminoisoquinolinylurea derivatives, which have demonstrated antiproliferative activity against melanoma cell lines. This highlights its potential in the development of novel anticancer drugs.
3. Used in Cross-Coupling Reactions:
1-Chloroisoquinoline is utilized in Mn-catalyzed cross-coupling reactions with aryland alkylmagnesium halides. These reactions are essential in the formation of carbon-carbon bonds, which are crucial for the synthesis of complex organic molecules.
4. Used in Pd-Catalyzed Cross-Coupling:
The compound is also used in Pd-catalyzed cross-coupling reactions with heteroaryl boronic acids and esters. These reactions are vital in the synthesis of various heterocycles and complex molecular structures, which find applications in pharmaceuticals, agrochemicals, and materials science.
5. Used in Homocoupling Reactions:
1-Chloroisoquinoline is employed in homocoupling reactions to yield bis-isoquinoline. The enantiomers of bis-isoquinoline can be used as chiral ligands for asymmetric synthesis, which is an essential aspect of modern pharmaceutical development.
6. Used in Controlling Storage Age and Stability:
1-Chloroisoquinoline can be applied to the control of storage age and stability of unstable boronic acids. This application is significant in the field of chemical synthesis, as it allows for the preservation and handling of sensitive reagents.

InChI:InChI=1/C9H6ClN/c10-9-8-4-2-1-3-7(8)5-6-11-9/h1-6H

Upstream product

• 1532-72-5 isoquinoline N-oxide 
• 1532-84-9 isoquinolin-1-ylamine 
• 4594-71-2 N-methylisocarbostyril 
• 63870-82-6 2-Ethyl-1,2-dihydroisochinolin-1-on 
• 491-30-5 1-hydroxyisoquinoline 
• 119-65-3 isoquinoline 
• 116833-54-6 4-toluenesulfonyl-sulfonyl-18O₂ 
• 491-30-5 1-isoquinolone 
• 10025-87-3 trichlorophosphate 
• 1984-23-2 p-nitrophenyl isocyanide 
• 486-73-7 1-isoquinolinecarboxylic acid 
• 120569-13-3 C₂₃H₁₆N₂O₂ 

Downstream Products

• 23165-19-7 4,4-dimethylmorpholinium chloride 
• 101439-09-2 (2-bromophenyl)isoquinolin-1-yl-acetonitrile 
• 23724-93-8 1-Methoxyisochinolin 
• 13797-20-1 isoquinolin-1-yl-phenyl-amine 
• 27302-13-2 α-phenyl-1-isoquinolineacetonitrile 
• 55577-53-2 1-iodo-2-methyl-isoquinolinium; iodide 
• 119-65-3 isoquinoline 
• 15793-94-9 1-hydrazino-isoquinoline 
• 66728-98-1 4-bromo-1-chloroisoqionoline 
• 56241-09-9 4-chloro-isoquinolin-1-ol 
• 491-30-5 1-hydroxyisoquinoline 
• 61259-58-3 4H-Benzoquinolizin-4-one 

Relevant academic research and scientific papers

Substituent effects of iridium complexes for highly efficient red OLEDs

This study reports substituent effects of iridium complexes with 1-phenylisoquinoline ligands. The emission spectra and phosphorescence quantum yields of the complexes differ from that of tris(1-phenylisoquinolinato-C 2, N) iridium(in) (Irpiq) depending on the substituents. The maximum emission peak, quantum yield and lifetime of those complexes ranged from 598-635 nm, 0.17-0.32 and 1.07-2.34 μs, respectively. This indicates the nature of the substituents has a significant influence on the kinetics of the excited-state decay. The substituents attached to phenyl ring have an influence on a stability of the HOMO. Furthermore, those substituents have effect on the contribution to a mixing between 3π-π and 3MLCT for the lowest excited states. Some of the complexes display the larger quantum yield than Irpiq, which has the quantum yield of 0.22. The organic light emitting diode (OLED) device based on tris [1-(4-fluoro-5-methylphenyl) isoquinolinato-C2,N]iridium(III) (Ir4F5Mpiq) yielded high external quantum efficiency of 15.5% and a power efficiency of 12.41m W-1 at a luminance of 218 cd m-2. An emission color of the device was close to an NTSC specification with CIE chromaticity characteristics of (0.66, 0.34). The Royal Society of Chemistry 2005.

Design, synthesis, and biological evaluation of isoquinolin-1(2H)-one derivates as tankyrase-1/2 inhibitors

To investigate structure-activity relationships of tankyrase (TNKS) inhibitors, twelve new derivatives of isoquinolin- 1(2H)-one were designed and synthesized, and biological assessments were conducted. Several potent TNKS inhibitors with single- or double-digit nanomolar IC50 values were identified using enzymatic assays. Compound 11c was the most potent compound of this series and inhibited TNKS1 and TNKS2 at an IC50 of 0.009 and 0.003 μM, respectively, and showed an IC50 of 0.029 μM in a DLD-1 SuperTopFlash assay. Molecular docking results showed that compound 11c occupied a unique subpocket and formed a hydrogen bond with Glu1138 of TNKS2, which was not consistent with the patterns of known TNKS inhibitors and thus warrants further research.

Preparation method of formaldehyde-substituted aza-condensed ring compound

The invention provides a preparation method of a formaldehyde-substituted aza-condensed ring compound, comprising the following steps: by using an aza-condensed ring lactam compound as a starting material, carrying out halogenation reaction, methylation reaction and methyl oxidation reaction to obtain the formaldehyde-substituted aza-condensed ring compound. According to the preparation method ofthe formaldehyde-substituted aza-condensed ring compound, the whole synthesis route is good in step repeatability, mild in operation condition and high in safety, and large-scale production and industrial popularization are facilitated; post-treatment energy consumption is low, a large amount of toxic wastewater is not generated, no pollution is caused to the environment, the production safety level and the production cost are reduced, application of green and environment-friendly industrial production is facilitated, and wide application prospects are achieved.

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

Site-Selective C–H Functionalization of (Hetero)Arenes via Transient, Non-symmetric Iodanes

Fosu, Hambira, and colleagues describe the direct C–H functionalization of medicinally relevant arenes or heteroarenes. This strategy is enabled by transient generation of reactive, non-symmetric iodanes from anions and PhI(OAc)2. The site-selective incorporation of Cl, Br, OMs, OTs, and OTf to complex molecules, including within medicines and natural products, can be conducted by the operationally simple procedure included herein. A computational model for predicting site selectivity is also included. The discovery of new medicines is a time- and labor-intensive process that frequently requires over a decade to complete. A major bottleneck is the synthesis of drug candidates, wherein each complex molecule must be prepared individually via a multi-step synthesis, frequently requiring a week of effort per molecule for thousands of candidates. As an alternate strategy, direct, post-synthetic functionalization of a lead candidate could enable this diversification in a single operation. In this article, we describe a new method for direct manipulation of drug-like molecules by incorporation of motifs with either known pharmaceutical value (halides) or that permit subsequent conversion (pseudo-halides) to medicinally relevant analogs. This user-friendly strategy is enabled by combining commercial iodine reagents with salts and acids. We expect this simple method for selective, post-synthetic incorporation of molecular diversity will streamline the discovery of new medicines. A strategy for C–H functionalization of arenes and heteroarenes has been developed to allow site-selective incorporation of various anions, including Cl, Br, OMs, OTs, and OTf. This approach is enabled by in situ generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc)2. The utility of this mechanism is demonstrated via para-selective chlorination of medicinally relevant arenes, as well as site-selective C–H chlorination of heteroarenes. Spectroscopic, computational, and competition experiments describe the unique nature, reactivity, and selectivity of these transient, unsymmetrical iodanes.

Rh(III)-Catalyzed [4 + 2] Self-Annulation of N-Vinylarylamides

An efficient rhodium(III)-catalyzed self-annulation of N-vinylarylamide has been developed. This reaction features a simple system and good reactivity with complete regioselectivity. The protocol provides easy access to an aminal incorporated dihydroisoqu

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

Application of 1,1-ADEQUATE, HMBC, and Density Functional Theory to Determine Regioselectivity in the Halogenation of Pyridine N-Oxides

The 1,1-ADEQUATE spectrum clearly shows specific two-bond proton to carbon correlations to unequivocally distinguish the major and minor regioisomers of ortho-halogenated pyridines and to aid in assignment of the corresponding proton and carbon chemical shifts. M06-2X/6-31+G(d,p) free energies of the regioisomeric intermediates arising from deprotonation correctly predict the experimentally observed preference and thus can be used to tune the substituent pattern to yield a desired regiochemical outcome.

Development of a facile and inexpensive route for the preparation of α-halobenzopyridines from α-unsubstituted benzopyridines

A facile and inexpensive route for the preparation of α-halobenzopyridines from α-unsubstituted benzopyridines via N-methylbenzopyridin-α-ones was developed. α-Unsubstituted benzopyridines were converted easily into the corresponding N-methylbenzopyridin-α-ones, which were halogenated using PPh3-TCICA or PPh3-DBICA without using solvent to give α-halobenzopyridines.

Highly Regioselective Halogenation of Pyridine N -Oxide: Practical Access to 2-Halo-Substituted Pyridines

A highly efficient and regioselective halogenation reaction of unsymmetrical pyridine N-oxide under mild conditions is described. The methodology provides a practical access to various 2-halo-substituted pyridines, which are pharmaceutically important intermediates.