1436-43-7

Basic information

• Product Name: QUINOLINE-2-CARBONITRILE
• Synonyms: QUINOLINE-2-CARBONITRILE;2-QUINOLINECARBONITRILE;2-Cyanoquinoline;2-Quinolinecarbonitrile ,97%;Quinaldonitrile;quinolin-2-carbonitrile;Quinoline-2-Carbinitrile;Quinolinecarbonitrile
• CAS NO: 1436-43-7
• Molecular Formula: C₁₀H₆N₂
• Molecular Weight: 154.17
• EINECS: 215-865-1
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Quinolines
• Mol File: 1436-43-7.mol

Chemical Properties

• Melting Point: 93-95 °C(lit.)
• Boiling Point: 160°C 23mm
• Flash Point: 160°C/23mm
• Appearance: /
• Density: 1.21
• Vapor Pressure: 0.000258mmHg at 25°C
• Refractive Index: 1.4820 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -0.56±0.40(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 115213
• CAS DataBase Reference: QUINOLINE-2-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: QUINOLINE-2-CARBONITRILE(1436-43-7)
• EPA Substance Registry System: QUINOLINE-2-CARBONITRILE(1436-43-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1436-43-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
QUINOLINE-2-CARBONITRILE is used as a key intermediate for the production of various organic compounds. Its unique chemical structure allows it to be a versatile building block in the synthesis of a wide range of molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, QUINOLINE-2-CARBONITRILE is used as an important raw material for the development of new drugs. Its properties make it a valuable component in the design and synthesis of novel therapeutic agents.
Used in Agrochemicals:
QUINOLINE-2-CARBONITRILE is also utilized in the agrochemical industry as a starting material for the synthesis of various agrochemical products, such as pesticides and herbicides.
Used in Dye Industry:
In the dye industry, QUINOLINE-2-CARBONITRILE serves as a crucial intermediate for the production of different types of dyes. Its ability to form various chemical bonds and structures makes it suitable for creating a wide array of dye compounds.
Used in the Production of Quinoline-2-carboxylic Acid Amide:
QUINOLINE-2-CARBONITRILE is specifically used to produce quinoline-2-carboxylic acid amide, which has its own set of applications in various fields, further expanding the utility of QUINOLINE-2-CARBONITRILE in the chemical industry.

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 4004, 1959 DOI: 10.1021/ja01524a046

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

Upstream product

• 830-60-4 2H-quinoline-1,2-dicarbonitrile 
• 612-62-4 2-Chloroquinoline 
• 74-90-8 hydrogen cyanide 
• 1613-37-2 Quinoline N-oxide 
• 151-50-8 potassium cyanide 
• 108-24-7 acetic anhydride 
• 126921-73-1 (E)-2-quinolinecarbaldehyde oxime 
• 13721-17-0 1-benzoyl-1,2-dihydro-quinoline-2-carbonitrile 
• 91-22-5 quinoline 
• 98-59-9 p-toluenesulfonyl chloride 
• 7677-24-9 trimethylsilyl cyanide 
• 2942-58-7 diethyl cyanophosphonate 
• 143-33-9 sodium cyanide 
• 128751-29-1 ethyl α-(2-cyano-1,2-dihydro-1-quinolinoxy)isobutyrate 

Downstream Products

• 1011-47-8 1-quinolin-2-yl-ethanone 
• 860717-00-6 3-[2]quinolyl-3-imino-2-phenyl-propionitrile 
• 16576-25-3 2-benzoylquinoline 
• 10421-37-1 1-[2]quinolyl-2-phenyl-ethanone 
• 5760-20-3 2-aminomethylquinoline 
• 93-10-7 quinoline-2-carboxylic acid 
• 96898-30-5 quinoline-2-thiocarboxamide 
• 18457-79-9 2-cyanoquinoline N-oxide 
• 119-61-9 benzophenone 
• 75458-19-4 3',4'-Dihydro-1'H-[2,4']biquinolinyl-2'-one 
• 120332-75-4 1-amino-2-cyanoquinolinium perchlorate 
• 39112-15-7 2-cyano-4-benzoylquinoline 
• 78905-66-5 2-(cyclohex-2-en-1-yl)quinolone 
• 220108-54-3 2-[4-(R)-phenyl-4,5-dihydrooxazolin-2-yl]quinoline 

Relevant articles and documents

Corrigendum: Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles (Chemistry - A European Journal, (2017), 23, 57, (14167-14172), 10.1002/chem.201703642)

The authors have been alerted to an error that was unfortunately missed at the time of publication. Table was duplicated with Table 4. The correct version of Table 2 is shown below. The authors apologise for any inconvenience caused. Organo-photoredox catalyzed oxidative dehydrogenation of tetrahydroquinolines (THQ).[a,b] (Table presented.) [a] Reaction conditions: 1 (0.5 mmol), rose bengal (1.0 mol %), N,N-dimethylacetamide (2.0 mL), open air atmosphere under visible-light irradiation at room temperature for 24 h. [b] Isolated yields. [c] 0.1 mol % of photoredox catalyst for 28 h.

(Benzo[h])quinolinyl-substituted monoazatriphenylenes: Synthesis and photophysical properties

We propose a method for the synthesis of quinolinyl- and benzo[h]quinolinylmonoazatriphenylenes through 1,2,4-triazine intermediates with subsequent transformations in aza-Diels-Alder reaction. The photophysical properties of these new compounds were examined, and the effects due to additional fused aromatic rings were explored.

Structure-function studies on a synthetic guanosine receptor that simultaneously binds Watson-Crick and Hoogsteen sites

A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via 1H NMR complexation studies in 5% DMSO-d6-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure-function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.

Rearrangements of 4-Quinolylcarbene, 3-Quinolylcarbene, and 2-Quinolylcarbene to 1-Naphthylnitrene and Cyanoindenes by Falling Solid Flash Vacuum Pyrolysis

The relationship between 4-quinolylcarbene 17, 3-quinolylcarbene 21, 2-quinolylcarbene 25, and 1-naphthylnitrene 35 has been explored experimentally and computationally. The diazomethylquinolines generated from (5-tetrazolyl)quinolines or 1,2,3-triazolo[1,5-a]quinoline by conventional flash vacuum pyrolysis (FVP) were observed by IR spectroscopy. The carbenes were generated by falling solid flash vacuum pyrolysis (FS-FVP). 4-Quinolylcarbene 17 was found to rearrange to 3-quinolylcarbene 21 and then to 2-quinolylcarbene 25, and finally via 1-naphthylnitrene 35 to 1-cyanoindene 36, which then isomerizes to 3- and 2-cyanoindenes 12 and 13. The thermal rearrangement of 2-quinolylcarbene to 1-naphthylnitrene was verified by ESR spectroscopy. The reaction mechanism has been elucidated with the help of calculations of the structures and energies of the quinolylcarbenes and 1-naphthylnitrene and the intervening aza-benzobicyclo[4.1.0]heptatrienes, aza-benzocycloheptatetraenes, and aza-benzocycloheptatrienylidenes and the transition states connecting them at the B3LYP/6-31G? level. The nonobserved 1,2-hydrogen shifts in aza-benzocycloheptatetraenes/aza-benzocycloheptatrienylidenes are found to have very high activation barriers.

One-pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride over silica gel, montmorillonites K-10, and KSF catalysts in dry media under microwave irradiation

A rapid and facile one-pot synthesis of nitriles has been carried out from the corresponding aldehydes and hydroxylamine hydrochloride in the presence of environmentally benign silica gel (84-95%), Mont K-10 (85-96%), and Mont KSF clay (88-98%) catalysts in dry media under microwave irradiation.

Regioselective direct oxidative C-H cyanation of quinoline and its derivatives catalyzed by vanadium-containing heteropoly acids

A direct oxidative C-H cyanation of quinoline and its derivatives using trimethylsilyl cyanide as the cyano source and molecular oxygen as the terminal oxidant has been developed. In the presence of catalytic amounts of vanadium-containing heteropoly acids, e.g., H7PV4Mo8O40, cyanation of various quinoline and its derivatives preferentially took place at the 4-position, affording the corresponding substituted 4-cyanoquinolines as the major products.

Triselenium dicyanide (TSD) as a new cyanation reagent: Synthesis of cyano pterins and quinoxalines along with library of cyano N-heterocyclic compounds

Triselenium dicynide (TSD) has been reported for the first time to be a novel cyanation reagent for the microwave-assisted one-pot synthesis of a series of various types of cyano N-heterocycles such as pterin, deazapterin, quinoxaline, naphthyridine, and

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 Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions

A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).