1198-30-7

Basic information

• Product Name: 1-Isoquinolinecarbonitrile
• Synonyms: ISOQUINOLINE-1-CARBONITRILE;1-CYANOISOQUINOLINE;1-ISOQUINOLINECARBONITRILE;TIMTEC-BB SBB002487;1-Cyanoisoquinoline 98%;ISOQUINOLIN-4-YLAMINE;soquinoline-1-carbonitrile;Isoquinaldinic nitrile
• CAS NO: 1198-30-7
• Molecular Formula: C₁₀H₆N₂
• Molecular Weight: 154.17
• EINECS: -0
• Product Categories: Heterocyclic Series;Quinolines, Isoquinolines & Quinoxalines;Quinoline&Isoquinoline;Quinolines;Quinolines, Isoquinolines & Quinoxalines;Building Blocks;Heterocyclic Building Blocks;Isoquinolines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 1198-30-7.mol
• Article Data: 37

Chemical Properties

• Melting Point: 90-92 °C(lit.)
• Boiling Point: 348.9 °C at 760 mmHg
• Flash Point: 121.609 °C
• Appearance: /
• Density: 1.211 g/cm³
• Vapor Pressure: 4.88E-05mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.48±0.30(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 119104
• CAS DataBase Reference: 1-Isoquinolinecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Isoquinolinecarbonitrile(1198-30-7)
• EPA Substance Registry System: 1-Isoquinolinecarbonitrile(1198-30-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1198-30-7(Hazardous Substances Data)

Usage

Uses

1-Isoquinolinecarbonitrile may be used as starting reagent in the syntheses of imidazo[5,1-a]isoquinolines.

Preparation

Phosphoryl chloride (0.54 g, 3.5 mmol) in chloroform (5 mL) was added dropwise to a solution of the requisite carbaldoxime (0.2 g, 1.2 mmol) in chloroform (10 mL) under ice-cooling. The mixture was heated under reflux for 4 h, treated with iced water, and the resulting precipitate was filtered off. The filtrate was basified with 28% ammonia and then extracted with chloroform to give 1-cyanoisoquinoline 1440; yield 0.17 g (95%).

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 4056, 1984 DOI: 10.1021/jo00195a036Tetrahedron Letters, 19, p. 589, 1978

General Description

Effect of magnetic field on the photosubstitution reaction of 1-isoquinolinecarbonitrile in ethanol has been reported. Conjugated polynitrile, plasma-polymerized 1-isoquinolinecarbonitrile (PPIQCN) has been prepared by plasma polymerization.

InChI:InChI=1/C10H6N2/c11-7-10-9-4-2-1-3-8(9)5-6-12-10/h1-6H

Upstream product

• 1532-72-5 isoquinoline N-oxide 
• 126921-66-2 isoquinoline-1-carbaldehyde-oxime 
• 844-25-7 2-benzoyl-1-cyano-1,2-dihydroisoquinoline 
• 67-56-1 methanol 
• 151-50-8 potassium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 2942-58-7 diethyl cyanophosphonate 
• 29924-67-2 2-acetyl-1,2-dihydro-isoquinoline-1-carbonitrile 
• 768-93-4 1-iodoadamantane 
• 53600-01-4 2-crotonyl-1-cyano-1,2-dihydroisoquinoline 
• 103360-21-0 1-cyano-2-ethoxycarbonyl-1,2-dihydroisoquinoline 
• 1035-19-4 2-phenylsulphonyl-1,2-dihydroisoquinoline-1-carbonitrile 
• 3340-68-9 2-(toluene-4-sulfonyl)-1,2-dihydro-isoquinoline-1-carbonitrile 
• 1436-44-8 isoquinoline-1-carboxamide 

Downstream Products

• 120332-66-3 NRB-04079 
• 120332-71-0 2-amino-1-cyanoisoquinolinium tosylate 
• 78905-67-6 1-(cyclohexyl-2-en-1-yl)isoquinoline 
• 58022-21-2 1-acetylisoquinoline 
• 40615-08-5 [(isoquinolin-1-yl)methyl]amine 
• 59175-48-3 1-(1H-tetrazol-5-yl)isoquinoline 
• 58021-72-0 (isoquinolin-1-yl)(4-methoxyphenyl)methanone 
• 16576-23-1 1-benzoylisoquinoline 
• 10134-00-6 (isoquinolin-1-yl)(3-methoxyphenyl)methanone 
• 10169-72-9 (3,4-dichlorophenyl)(isoquinolin-1-yl)methanone 
• 1177408-19-3 (isoquinolin-1-yl)(3-fluorophenyl)methanone 
• 16576-24-2 (isoquinolin-1-yl)(4-chlorophenyl)methanone 
• 1177408-14-8 (isoquinolin-1-yl)(2-trifluoromethylphenyl)methanone 
• 497058-93-2 (isoquinolin-1-yl)(4-trifluoromethylphenyl)methanone 

Relevant articles and documents

A PASE-based approach towards 12-(1H-1,2,3-triazol-1-yl)-indolo[2,1-a]isoquinolines via the reaction of 3-(isoquinolin-1-yl)-1,2,4-triazines with benzyne

12-(1H-1,2,3-Triazol-1-yl)indolo[2,1-a]isoquinolines are prepared in 51–56% yields using a PASE (pot, atom, step, economic)-based approach, namely, by the reaction between available 5-R-6-Ar-3-(isoquinolin-1-yl)-1,2,4-triazines and in situ generated benzyne. A mechanism comprising domino-transformation was suggested, and the structure of one key product was confirmed by a single crystal X-ray diffraction analysis.

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Studies on tertiary amine oxides. LXIII. Nitration of 1-cyanoisoquinoline 2-oxide and isoquinoline 2-oxide

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Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions

Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is

Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical?radical cross-coupling powered by visible light photocatalysis

Transition-metal-catalyzed C?N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical?radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C?N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C?N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.