25309-65-3

Basic information

• Product Name: 4-Ethylbenzonitrile
• Synonyms: P-ETHYLBENZONITRILE;4-ETHYLBENZONITRILE;p-Ethylbenzonitrile 4-Ethyl Benzonitrile;4-ethylbenzenecarbonitrile
• CAS NO: 25309-65-3
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17
• EINECS: 246-811-5
• Product Categories: Aromatic Nitriles;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 25309-65-3.mol
• Article Data: 30

Chemical Properties

• Melting Point: 51.75°C (estimate)
• Boiling Point: 237 °C(lit.)
• Flash Point: 208 °F
• Appearance: /
• Density: 0.956 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0824mmHg at 25°C
• Refractive Index: n20/D 1.527(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 2040912
• CAS DataBase Reference: 4-Ethylbenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethylbenzonitrile(25309-65-3)
• EPA Substance Registry System: 4-Ethylbenzonitrile(25309-65-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 25309-65-3(Hazardous Substances Data)

Usage

Description

4-Ethylbenzonitrile is an electron-deficient aromatic nitrile, characterized by its unique chemical structure and properties. It is a valuable intermediate in various chemical reactions and synthesis processes.

Uses

Used in Chemical Synthesis:
4-Ethylbenzonitrile is used as a nickel oxide catalyst in the preparation method and its application in the synthesis of pyrimidine derivatives. It plays a crucial role in facilitating the formation of these important heterocyclic compounds, which are widely used in pharmaceuticals, agrochemicals, and other industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Ethylbenzonitrile is used as a key intermediate in the synthesis of various drug molecules. Its unique structure allows for the formation of diverse chemical entities with potential therapeutic applications.
Used in Agrochemical Industry:
4-Ethylbenzonitrile is also utilized in the agrochemical industry for the synthesis of active ingredients in pesticides and herbicides. Its electron-deficient nature makes it a suitable candidate for the development of new and effective agrochemical products.
Used in Organic Synthesis:
In organic synthesis, 4-Ethylbenzonitrile is used as a versatile building block for the preparation of various organic compounds. It can be employed in the synthesis of 2-(3-bromo-phenyl)-4,6-bis-(4-ethyl-phenyl)-[1,3,5]-triazine, a compound with potential applications in various fields.
Used in Preparation of Mixture Compounds:
4-Ethylbenzonitrile may be used in the preparation of mixtures, such as 1-benzyl-2-methylbenzene and 1-benzyl-4-methylbenzene. These mixtures can be further utilized in various applications, including the synthesis of specialty chemicals and materials.

InChI:InChI=1/C9H9N/c1-2-8-3-5-9(7-10)6-4-8/h3-6H,2H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 100-41-4 ethylbenzene 
• 75-05-8 acetonitrile 
• 33695-58-8 4-ethylbenzamide 
• 50325-49-0 p-vinylbenzylamine 
• 622-98-0 4-chloro(ethylbenzene) 
• 124-38-9 carbon dioxide 
• 25309-64-2 4-ethyl-1-iodobenzene 
• 4748-78-1 4-ethylbenzylaldehyde 
• 3435-51-6 4-ethenylbenzonitrile 
• 3032-92-6 4-cyanophenylacetylene 
• 623-03-0 4-Cyanochlorobenzene 
• 2386-64-3 ethylmagnesium chloride 
• 97-94-9 triethyl borane 

Downstream Products

• 55843-91-9 4-(H-imidazo[1,2-a]pyridin-2-yl)benzonitrile 
• 20488-11-3 4-(1-chloroethyl)benzonitrile 
• 742699-27-0 1-(4-ethylphenyl)-3-phenylprop-2-yn-1-one 
• 1443-80-7 4-cyanophenyl methyl ketone 
• 20099-89-2 4-Cyanophenacyl bromide 
• 3034-34-2 4-cyanobenzamide 
• 102494-85-9 (4-ethylphenyl)methanamine monohydrochloride 
• 1620330-18-8 2,4,6-tris(4-ethylphenyl)-1,3,5-triazine 
• 1620330-19-9 (4-ethylphenyl)(2,4,6-trimethoxyphenyl)methanone 
• 713-36-0 2-benzyltoluene 

Relevant articles and documents

Boosting homogeneous chemoselective hydrogenation of olefins mediated by a bis(silylenyl)terphenyl-nickel(0) pre-catalyst

The isolable chelating bis(N-heterocyclic silylenyl)-substituted terphenyl ligand [SiII(Terp)SiII] as well as its bis(phosphine) analogue [PIII(Terp)PIII] have been synthesised and fully characterised. Their reaction with Ni(cod)2(cod = cycloocta-1,5-diene) affords the corresponding 16 VE nickel(0) complexes with an intramolecularη2-arene coordination of Ni, [E(Terp)E]Ni(η2-arene) (E = PIII, SiII; arene = phenylene spacer). Due to a strong cooperativity of the Si and Ni sites in H2activation and H atom transfer, [SiII(Terp)SiII]Ni(η2-arene) mediates very effectively and chemoselectively the homogeneously catalysed hydrogenation of olefins bearing functional groups at 1 bar H2pressure and room temperature; in contrast, the bis(phosphine) analogous complex shows only poor activity. Catalytic and stoichiometric experiments revealed the important role of the η2-coordination of the Ni(0) site by the intramolecular phenylene with respect to the hydrogenation activity of [SiII(Terp)SiII]Ni(η2-arene). The mechanism has been established by kinetic measurements, including kinetic isotope effect (KIE) and Hammet-plot correlation. With this system, the currently highest performance of a homogeneous nickel-based hydrogenation catalyst of olefins (TON = 9800, TOF = 6800 h?1) could be realised.

Environmentally responsible, safe, and chemoselective catalytic hydrogenation of olefins: ppm level Pd catalysis in recyclable water at room temperature

Textbook catalytic hydrogenations are typically presented as reactions done in organic solvents and oftentimes under varying pressures of hydrogen using specialized equipment. Catalysts new and old are all used under similar conditions that no longer reflect the times. By definition, such reactions are both environmentally irresponsible and dangerous, especially at industrial scales. We now report on a general method for chemoselective and safe hydrogenation of olefins in water using ppm loadings of palladium from commercially available, inexpensive, and recyclable Pd/C, together with hydrogen gas utilized at 1 atmosphere. A variety of alkenes is amenable to reduction, including terminal, highly substituted internal, and variously conjugated arrays. In most cases, only 500 ppm of heterogeneous Pd/C is sufficient, enabled by micellar catalysis used in recyclable water at room temperature. Comparison with several newly introduced catalysts featuring base metals illustrates the superiority of chemistry in water.

Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species

Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.