19493-44-8

Basic information

• Product Name: 1-Chloroisoquinoline
• Synonyms: 1-Chloroisoquinone;Isoquinoline, 1-chloro-;1-Chloroisoquinoline 95%;1-chloro-1,2-dihydroisoquinoline;1-CHLOROISOQUINOLINE;1-CHLOROISOQUINOLINE, 98.0+%(GC);chloroisoquinoline;1-Chloroisoquinoline, 97+%
• CAS NO: 19493-44-8
• Molecular Formula: C₉H₆ClN
• Molecular Weight: 163.6
• EINECS: -0
• Product Categories: Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocyclic Series;Quinolines;Halogenated Heterocycles;Heterocyclic Building Blocks;Isoquinolines;IsoquinolinesBuilding Blocks;Other Products;Building Blocks;Chemical Synthesis
• Mol File: 19493-44-8.mol
• Article Data: 31

Chemical Properties

• Melting Point: 31-36 °C(lit.)
• Boiling Point: 274-275 °C768 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to yellow/Low Melting Solid, Crystals and/or Chunks
• Density: 1.2108 (rough estimate)
• Vapor Pressure: 0.00902mmHg at 25°C
• Refractive Index: 1.6342 (estimate)
• Storage Temp.: 0-10°C
• PKA: 2.03±0.30(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 2996
• CAS DataBase Reference: 1-Chloroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloroisoquinoline(19493-44-8)
• EPA Substance Registry System: 1-Chloroisoquinoline(19493-44-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 19493-44-8(Hazardous Substances Data)

Usage

Chemical Description

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

Description

1-Chloroisoquinoline is an organic compound with the molecular formula C9H6ClNO and is characterized by its white to yellow low melting solid appearance, often found in crystalline form. It is a derivative of isoquinoline, featuring a chlorine atom attached to the first carbon position. 1-Chloroisoquinoline is known for its significant applications in various chemical and pharmaceutical processes due to its unique structure and reactivity.

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 
• 120569-13-3 C₂₃H₁₆N₂O₂ 
• 491-30-5 1-isoquinolone 
• 10025-87-3 trichlorophosphate 
• 1984-23-2 p-nitrophenyl isocyanide 
• 486-73-7 1-isoquinolinecarboxylic acid 

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 articles and documents

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.

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.