4686-14-0

Basic information

• Product Name: (2Z)-phenyl(phenylimino)ethanenitrile
• Synonyms: (2Z)-Phenyl(phenylimino)ethanenitrile; N-Phenylbenzimidoyl cyanide
• CAS NO: 4686-14-0
• Molecular Formula: C₁₄H₁₀N₂
• Molecular Weight: 206.2426
• Mol File: 4686-14-0.mol

Chemical Properties

• Boiling Point: 339.3°C at 760 mmHg
• Flash Point: 159°C
• Density: 1.01g/cm³
• Vapor Pressure: 9.28E-05mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: (2Z)-phenyl(phenylimino)ethanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-phenyl(phenylimino)ethanenitrile(4686-14-0)
• EPA Substance Registry System: (2Z)-phenyl(phenylimino)ethanenitrile(4686-14-0)

Safety Data

• Hazardous Substances Data: 4686-14-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2Z)-phenyl(phenylimino)ethanenitrile is utilized as a key intermediate in various organic synthesis reactions. Its unique structure allows it to participate in a range of chemical transformations, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Production:
(2Z)-phenyl(phenylimino)ethanenitrile serves as a building block in the production of pharmaceuticals. Its presence in drug formulations can be attributed to its ability to form essential molecular structures that contribute to the therapeutic effects of medications.
Used in Agrochemicals:
(2Z)-phenyl(phenylimino)ethanenitrile is also employed in the development of agrochemicals. Its role in this industry is linked to its capacity to create molecules with specific properties that can be used in agricultural applications, such as pest control or crop protection.
Used in Materials Science:
(2Z)-phenyl(phenylimino)ethanenitrile may have potential applications in materials science, where its structural features could be leveraged to develop new materials with unique properties for various uses.
Used in Industrial Manufacturing Processes:
(2Z)-phenyl(phenylimino)ethanenitrile could be integrated into industrial manufacturing processes, where its chemical properties might be harnessed to improve the production of certain goods or to create novel products with specific characteristics.

Upstream product

• 140-29-4 phenylacetonitrile 
• 586-96-9 Nitrosobenzene 
• 100-52-7 benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 67-63-0 isopropyl alcohol 
• 4553-59-7 2-anilino-2-phenylacetonitrile 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 62-53-3 aniline 
• 538-51-2 benzylidene phenylamine 
• 3433-21-4 α-Cyano-α,N-diphenylnitrone 
• 3433-20-3 (oxy-phenyl-imino-(seqcis))-phenyl-acetonitrile 
• 773837-37-9 sodium cyanide 
• 4198-95-2 α-phenylimino-deoxybenzoin 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 74-90-8 hydrogen cyanide 
• 62-53-3 aniline 
• 65-85-0 benzoic acid 
• 1363411-11-3 4-methylene-5-oxo-1,2-diphenylpyrrolidine-2-carbonitrile 
• 148903-67-7 β-benzoyl-2-methylenepropionic acid methyl ester 
• 93-98-1 N-phenyl benzoyl amide 
• 1363411-10-2 methyl 4-cyano-2-methylene-4-phenyl-4-(phenylamino)butanoate 
• 1363411-26-0 C₂₅H₂₂N₂O₂ 
• 134-81-6 benzil 

Relevant articles and documents

Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation

A new protocol for the direct formation of amides from imines derived from aromatic aldehydes via metal-free aerobic oxidation in the presence of cyanide is described. This protocol was applicable to various aldimines, and the desired amides were obtained in moderate to good yields. Mechanistic studies suggested that this aerobic oxidative amidation might proceed via the addition of cyanide to imines followed by proton transfer from carbon to nitrogen in the original imines, leading to carbanions of α-amino nitriles, which undergo subsequent oxidation with molecular oxygen in air to provide the desired amide compounds.

Reduction of 1,2-dicarbonyl compounds and of their N-phenylimine derivatives by sodium cyanide under aprotic conditions

Some aromatic 1,2-dicarbonyl compounds, i.e. 9,10-phenanthrenequinone, acenaphthenequinone and benzil, and their corresponding N-phenyl monoimines, have been reduced, using dry acetonitrile as the solvent, in the presence of sodium cyanide as a reducing agent. Comparative potentiostatic preparative-scale electrolysis is described.

Synthesis of iminonitriles by oxone/tbab-mediated one-pot oxidative three-component strecker reaction

Oxidative three-component reaction of aldehydes, amines, and TMSCN in a biphasic solvent system (toluene/H2O) containing Oxone, tetra-n-butylammonium bromide (TBAB) and sodium bicarbonate afforded α-iminonitriles in good to excellent yields. This oxidative Strecker reaction was applicable to a wide range of aldehydes and amines, aromatic or aliphatic, of different electronic and steric properties. Substituted 1-aza-2-cyano-1,3-dienes were also accessible using α,β-unsaturated aldehydes as inputs.

Construction of highly functional α-amino nitriles via a novel multicomponent tandem organocatalytic reaction: A facile access to α-methylene γ-lactams

The first tertiary amine-catalyzed multicomponent tandem Strecker-allylic-alkylation (SAA) reaction has been developed, which provides a facile access to functionalized α-amino nitriles, which could be readily converted into α-methylene-γ-butyrolactams. The Royal Society of Chemistry 2012.

Elusive ethynyl azides: Trapping by 1,3-dipolar cycloaddition and decomposition to cyanocarbenes

Although they decompose rapidly to produce cyanocarbenes, ethynyl azides were generated from (chloroethynyl)arenes and trapped for the first time by 1,3-dipolar cycloaddition at cyclooctyne.

Synthesis of highly functionalized 2(1H)-pyrazinone 3-carboxamide scaffolds

(Chemical Equation Presented) Synthesis of highly functionalized 2(1H)-pyrazinone 3-carboxamide derivatives is reported. A one-pot, two-step process including the base-mediated reaction of N,N-disubstituted aminoacetonitrile derivatives 18 with 3,5-dihalo

One-pot three-component sysnthesis of α-iminonitriles by IBX/TBAB-mediated oxidative strecker reaction

The reaction of aldehydes, amines, and TMSCN in the presence of 2-iodoxybenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) afforded α-iminonitriles in good to excellent yields under mild conditions. The presence of TBAB is essential for this transformation. The methodology was applied to a two-step synthesis of indolizidine via a microwave-assisted intramolecular cycloaddition of α-iminonitrile.

Lithium bromide catalyzed Ehrlich-Sachs reactions using solvent-free conditions

Lithium bromide proves to be an efficient catalyst for Ehrlich-Sachs reaction of nitroso arenes with active methylene compounds under microwave irradiation through simple solvent-free reaction conditions.

Oxidation of amines with hyper valent Tert-butylperoxyiodanes: Synthesis of imines and Tert-butylperoxyamino acetalsh

Reaction of secondary amines with 1-tert-butylperoxy-1,2-benziodoxol-3(1H)-one (2) undergoes dehydrogenation to afford imines in the presence of K2CO3, while oxidation of tertiary amines without base produces tert-butylperoxyamino acetals.

Synthesis of Nitrogen Heterocycles by Condensation of the Conjugate Base of Open-Chain Reissert Compound Analogs with Vinyltriphenylphosphonium Bromide (Schweizer's Salt)

Reaction of the conjugate base of several open-chain Reissert compound analogs with vinyltriphenylphosphonium bromide is shown to afford a convenient route to substituted pyrroles.The condensation is a two-step process involving an initial reversible addition to form an unstabilized Wittig reagent followed by an intramolecular Wittig reaction upon the carbonyl group of the tertiary amide functionality with concomitant elimination of HCN.Several applications to the synthesis of 1,2,5-trisubstituted pyrroles are presented, together with attempts to expand this methodology to the synthesis of other heterocyclic systems.