1823-99-0

Basic information

• Product Name: 3-aminocinnamonitrile
• Synonyms: 3-aminocinnamonitrile;3-Amino-3-phenylpropenenitrile;3-Phenyl-3-aminoacrylonitrile;β-Aminobenzeneacrylonitrile;3-amino-3-phenylprop-2-enenitrile
• CAS NO: 1823-99-0
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.17322
• EINECS: 217-355-4
• Mol File: 1823-99-0.mol

Chemical Properties

• Boiling Point: 379.7°Cat760mmHg
• Flash Point: 183.5°C
• Appearance: /
• Density: 1.101g/cm³
• Vapor Pressure: 5.73E-06mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 3-aminocinnamonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-aminocinnamonitrile(1823-99-0)
• EPA Substance Registry System: 3-aminocinnamonitrile(1823-99-0)

Safety Data

• Hazardous Substances Data: 1823-99-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Aminocinnamonitrile is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique structural features that facilitate the creation of complex organic molecules.
Used in Agrochemical Production:
3-aminocinnamonitrile is also utilized as a building block in the production of agrochemicals, where its reactivity and functional groups contribute to the development of effective insecticides and other agricultural products.
Used in Drug Discovery and Development:
3-Aminocinnamonitrile is used as a potential candidate in drug discovery and development, given its demonstrated medicinal properties and the ongoing research into its applications in this field.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Aminocinnamonitrile is used as a versatile reactant for the preparation of a wide range of important compounds, including antiviral agents, highlighting its utility across different chemical and biological applications.

InChI:InChI=1/C9H8N2/c10-7-6-9(11)8-4-2-1-3-5-8/h1-6H,11H2/b9-6-

Upstream product

• 100-47-0 benzonitrile 
• 75-05-8 acetonitrile 
• 99749-00-5 lithioacetonitrile 
• 536-74-3 phenylacetylene 
• 614-16-4 Benzoylacetonitrile 
• 60-29-7 diethyl ether 
• 14904-36-0 cis-trans-3--cinnamonitril 
• 14904-42-8 cis-trans-3-Trimethylsilylamino-cinnamonitril 
• 3755-96-2 (2Z)-3-bromo-3-phenylprop-2-enenitrile 
• 140-29-4 phenylacetonitrile 

Downstream Products

• 21628-33-1 6-amino-3-cyano-2,4-diphenylpyridine 
• 4847-47-6 β-(phenylamino)-cinnamic acid nitrile 
• 100784-53-0 6-hydroxy-2,4-diphenyl-nicotinonitrile 
• 33831-53-7 4-hydroxy-6-methyl-2-phenyl-nicotinonitrile 
• 3435-29-8 4-Amino-6-phenylpyrimidine 
• 1563-41-3 2-(α-amino-benzyliden)-5-oxo-hex-3-enenitrile 
• 61378-38-9 2,4,6-triphenyl-1,4-dihydropyridine-3,5-dicarbonitrile 
• 68063-28-5 5-oxo-2,4-diphenyl-4,5-dihydro-1H-indeno[1,2-b]pyridine-3-carbonitrile 
• 846550-70-7 5-cyano-2-methyl-6-phenyl-nicotinic acid ethyl ester 

Relevant articles and documents

Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp2)-H Alkynylation of Acceptor-Substituted Enamines

A gold-catalyzed synthesis of tetrasubstituted 1,3-enynes from hypervalent iodine(III) reagents and activated alkenes is reported. This reaction involves an in situ formed alkynyl Au(III) species and a subsequent direct C(sp2)-H functionalization of alkenes, offering 26 enynes in 62-92% yield with excellent functional group tolerance.

Green synthesis method of nicotinic acid ester compounds based on non-metallic conditions

The invention discloses a green synthesis method based on nicotinic acid ester compounds under non-metallic conditions, and belongs to the technical field of organic synthesis. The method comprises the following steps of (III) replacing cyclopropanol and (II) substituted enamine ester as a raw material, taking tetramethyl piperidine nitrogen oxide as an oxidizing agent, 110 - 130 °C, stirring and reacting in an organic solvent to synthesize a (I) nicotinate compound. The invention provides a green synthesis method based on nicotinic acid ester compounds under non-metallic conditions, wherein cyclopropanols and enamine esters are taken as raw materials, and a polysubstituted nicotinate is synthesized through a strategy of oxidative dehydrogenation of ketene cyclization.

Multi-component synthesis of 3-substituted indoles and their cyclisation to α-carbolines: Via I2-promoted intramolecular C2 oxidative amination/aromatisation at room temperature

Condensation of indoles, aldehydes and pyrazol-5-amine in the presence of ceric ammonium nitrate gives 3-substituted indoles. These then cyclise to α-carbolines at room temperature through I2-promoted intramolecular C2 amination and aromatisation in open air. A plausible mechanism is proposed based on some controlled experiments.

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process.

Tandem Thorpe Reaction/Palladium Catalyzed Asymmetric Allylic Alkylation: Access to Chiral β-enaminonitriles with Excellent Enantioselectivity

A new type of nucleophile, a 3-imino nitrile carbanion generated in situ by Thorpe reaction of acetonitrile with a base, was developed successfully and applied in a Pd-catalyzed asymmetric allylic alkylation with mono-substituted allyl reagents under Pd/S

In situ click chemistry generation of cyclooxygenase-2 inhibitors

Cyclooxygenase-2 isozyme is a promising anti-inflammatory drug target, and overexpression of this enzyme is also associated with several cancers and neurodegenerative diseases. The amino-acid sequence and structural similarity between inducible cyclooxygenase-2 and housekeeping cyclooxygenase-1 isoforms present a significant challenge to design selective cyclooxygenase-2 inhibitors. Herein, we describe the use of the cyclooxygenase-2 active site as a reaction vessel for the in situ generation of its own highly specific inhibitors. Multi-component competitive-binding studies confirmed that the cyclooxygenase-2 isozyme can judiciously select most appropriate chemical building blocks from a pool of chemicals to build its own highly potent inhibitor. Herein, with the use of kinetic target-guided synthesis, also termed as in situ click chemistry, we describe the discovery of two highly potent and selective cyclooxygenase-2 isozyme inhibitors. The in vivo anti-inflammatory activity of these two novel small molecules is significantly higher than that of widely used selective cyclooxygenase-2 inhibitors.

Acid-promoted rapid solvent-free access to substituted 1,4-dihydropyridines from β-ketothioamides

β-Ketothioamides (KTAs) have been used as building blocks with aldehydes and β-enaminonitriles for synthesis of 1,4-dihydropyridines in the presence of AcOH under solvent-free conditions within 5 min. This new strategy exhibits remarkable features such as high chemoselectivity, mild reaction conditions, easily available substrates, and good yields.

Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870

A range of β-aminonitriles (3-amino-3-phenylpropanenitrile and derivatives) were synthesised by reaction of various benzonitriles with acetonitrile and subsequent reduction of the resulting acrylonitrile products. These compounds were hydrolysed to the co

Rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylonitriles

The rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylonitriles was investigated by using monophosphine and bisphosphine ligands. It was found that an Rh-QuinoxP complex exhibited high enantioselectivities for β-aryl substituted β-acetylamino acrylonitriles and the Rh-JosiPhos CyPF-t-Bu complex was proven to be effective for the hydrogenation of tetrasubstituted olefins from cyclic β-acetylamino acrylonitriles.

Design and synthesis of substituted N-(1,3-diphenyl-1H-pyrazol-5-yl) benzamides as positive allosteric modulators of the metabotropic glutamate receptor subtype 5

Based on SAR in the alkyne class of mGlu5 receptor negative allosteric modulators and a set of amide-based positive allosteric modulators, optimized substitution of the aryl bring was used to create substituted N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides.