60138-76-3

Basic information

• Product Name: 2-(DIMETHYLAMINO)NICOTINONITRILE
• Synonyms: 2-(DIMETHYLAMINO)NICOTINONITRILE;2-(dimethylamino)-pyridine-3-carbonitrile;3-pyridinecarbonitrile, 2-(dimethylamino)-;3-Cyano-2-dimethylaminopyridine;2--5-nitropyridine;2-(diMethylaMino)-3-Pyridinecarbonitrile
• CAS NO: 60138-76-3
• Molecular Formula: C8H9N3
• Molecular Weight: 147.17716
• Mol File: 60138-76-3.mol

Chemical Properties

• Boiling Point: 264.861ºC at 760 mmHg
• Flash Point: 113.984ºC
• Appearance: /
• Density: 1.113g/cm3
• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: Room temperature.
• PKA: 3.76±0.10(Predicted)
• CAS DataBase Reference: 2-(DIMETHYLAMINO)NICOTINONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(DIMETHYLAMINO)NICOTINONITRILE(60138-76-3)
• EPA Substance Registry System: 2-(DIMETHYLAMINO)NICOTINONITRILE(60138-76-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 60138-76-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(Dimethylamino)nicotinonitrile is used as a chemical intermediate for the synthesis of biologically active molecules, contributing to the development of new drugs. Its unique structure allows it to be a key component in the creation of pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(Dimethylamino)nicotinonitrile serves as a precursor in the synthesis of agrochemicals, aiding in the development of new pesticides or other agricultural chemicals that can enhance crop protection and yield.
Used in Organic Material Synthesis:
2-(Dimethylamino)nicotinonitrile is utilized as a building block in the synthesis of organic materials, playing a crucial role in the formation of advanced materials with specific properties for various applications.
Used as a Catalyst in Organic Reactions:
2-(DIMETHYLAMINO)NICOTINONITRILE also functions as a catalyst to facilitate organic reactions, enhancing the efficiency and selectivity of chemical processes in the synthesis of complex organic molecules.
Used in Material Science:
2-(Dimethylamino)nicotinonitrile is employed in the development of new materials, where its unique properties can be harnessed to create innovative solutions for a wide range of industries, including electronics, energy, and advanced manufacturing.

InChI:InChI=1/C8H9N3/c1-11(2)8-7(6-9)4-3-5-10-8/h3-5H,1-2H3

Upstream product

• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 68-12-2 N,N-dimethyl-formamide 
• 127-19-5 N,N-dimethyl acetamide 
• 3939-13-7 3-cyano-2-fluoropyridine 
• 24517-64-4 2-amino-3-pyridinecarbonitrile 

Downstream Products

• 354824-09-2 3-(aminomethyl)-N,N-dimethylpyridin-2-amine 

Relevant articles and documents

A Novel One-Pot Synthesis of N,N-Dimethylaminopyridines by Diazotization of Aminopyridines in Dimethylformamide in the Presence of Trifluoromethanesulfonic Acid

Abstract: Diazotization of aminopyridines in the presence of trifluoromethanesulfonic acid gives the corresponding pyridinyl trifluoromethanesulfonates instead of expected diazonium salts. Pyridinyl trifluoromethanesulfonates can be converted to N,N-dimethylaminopyridines on heating in dimethylformamide via replacement of the trifluoromethanesulfonyloxy group. The reaction is accelerated under microwave irradiation. A novel one-pot procedure has been proposed for the synthesis of 2- and 4-(dimethylamino)pyridines from commercially available aminopyridines. The procedure provides high yields of the target products, and it can be regarded as an alternative to the known methods of synthesis of N,N-dimethylpyridin-4-amine (DMAP) widely used as base catalyst in organic synthesis.

Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides

A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the reactivity of an aromatic halide is F > Cl > Br > I, the reactivity of aromatic halides in this system was found to be I > Br a‰ F > Cl. This protocol also showed a good regioselectivity for multihalogenated aromatics. This protocol is valuable for industrial application due to the simplicity of operation, the unrestricted availability of amino sources and aromatic halides, transition metal-free conditions, no requirement for solvent, and scalability.

Microwave irradiation-assisted amination of 2-chloropyridine derivatives with amide solvents

A simple, quick, and high-yielding microwave-assisted synthesis of 2-(N,Ndimethyl) amine- and 2-aminopyridine derivatives is reported here for the first time in the reaction of 2-chloro substituted pyridines with amide solvents such as dimethylformamide or formamide, without transition-metal catalysts. Taylor & Francis Group, LLC.

A simple synthesis of aminopyridines: Use of amides as amine source

A transition metal/microwave irradiation (or base) free synthesis of aminopyridines has been accomplished via C-N bond forming reaction between chloropyridine and a variety of simple amides under refuxing conditions.

Microwave-induced by-products in the synthesis of 2-(4-methyl-2-phenylpiperazinyl)pyridine-3-carbonitrile

The Letter describes the investigation of an industrial reaction of N-methylphenylpiperazine and chloronicotinonitrile, under microwave heating. Besides the formation of the expected 2-(4-methyl-2-phenylpiperazinyl)pyridine-3-carbonitrile (4), extension o