7599-05-5

Basic information

• Product Name: (4-nitrophenyl)(phenyl)acetonitrile
• CAS NO: 7599-05-5
• Molecular Formula: C₁₄H₁₀N₂O₂
• Molecular Weight: 238.2414
• Mol File: 7599-05-5.mol

Chemical Properties

• Boiling Point: 400.2°C at 760 mmHg
• Flash Point: 195.9°C
• Density: 1.245g/cm³
• Vapor Pressure: 1.29E-06mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: (4-nitrophenyl)(phenyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (4-nitrophenyl)(phenyl)acetonitrile(7599-05-5)
• EPA Substance Registry System: (4-nitrophenyl)(phenyl)acetonitrile(7599-05-5)

Safety Data

• Hazardous Substances Data: 7599-05-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(4-nitrophenyl)(phenyl)acetonitrile is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs and improving existing ones.
Used in Dye Industry:
(4-nitrophenyl)(phenyl)acetonitrile is used as a starting material for the production of dyes, enabling the creation of a wide range of colors and properties for various applications.
Used in Agrochemical Industry:
(4-nitrophenyl)(phenyl)acetonitrile is used as a component in the manufacture of agrochemicals, such as pesticides and herbicides, to help protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
(4-nitrophenyl)(phenyl)acetonitrile is used as a common starting material for the synthesis of various organic compounds, facilitating the creation of new chemical entities and advancing scientific research.

Upstream product

• 140-29-4 phenylacetonitrile 
• 100-00-5 4-chlorobenzonitrile 
• 100-25-4 para-dinitrobenzene 
• 555-16-8 4-nitrobenzaldehdye 
• 13031-13-5 2-methoxy-2-phenylacetonitrile 
• 98-95-3 nitrobenzene 
• 32121-27-0 α-phenoxy-α-phenylacetonitrile 
• 89278-08-0 (4-Chloro-phenoxy)-phenyl-acetonitrile 
• 72301-64-5 α-(2,4-Dichlorophenoxy)phenylacetonitrile 
• 350-46-9 4-Fluoronitrobenzene 
• 110-86-1 pyridine 
• 67755-90-2 Ethoxy-1-ethoxy-(phenyl)-acetonitrile 
• 532-28-5 (RS)-mandelonitrile 

Downstream Products

• 1144-74-7 4-nitrobenzophenone 
• 56577-69-6 Bis-(4-nitrophenyl)cyanomethane 
• 159191-20-5 3-cyano-3-(4-nitrophenyl)-3-phenylpropionyl chloride 
• 159191-22-7 3-Cyano-3-(4-nitro-phenyl)-3-phenyl-propionic acid 
• 19497-20-2 N₁,N₁,N₃,N₃-tetramethylguanidinium 
• 159191-21-6 3-Cyano-3-(4-nitro-phenyl)-3-phenyl-propionic acid ethyl ester 

Relevant articles and documents

On the Mechanism of the Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes

On the basis of the isotope effect and the effect of base on the reaction rate the main features of the mechanism of the vicarious nucleophilic substitution of hydrogen were established.The reaction proceeds via fast and reversible addition of the carbanions to the nitroarenes followed by slower base-induced β-elimination.

Simple Synthesis of Aryl p-Nitroarylacetonitriles by Vicarious Nucleophilic Substitution with Carbanions of Protected Cyanohydrins

Acetals of the cyanohydrins of aromatic aldehydes were deprotonated to generate carbanions, which were used in the vicarious nucleophilic substitution of the hydrogen atom of aromatic and heteroaromatic nitro compounds to form p-nitro-substituted diarylac

Transition metal-free direct dehydrogenative arylation of activated C(sp3)-H bonds: Synthetic ambit and DFT reactivity predictions

A transition metal-free dehydrogenative method for the direct mono-arylation of a wide range of activated C(sp3)-H bonds has been developed. This operationally simple and environmentally friendly aerobic arylation uses tert-BuOK as the base and nitroarenes as electrophiles to prepare up to gram quantities of structurally diverse sets (>60 examples) of α-arylated esters, amides, nitriles, sulfones and triaryl methanes. DFT calculations provided a predictive model, which states that substrates containing a C(sp3)-H bond with a sufficiently low pKa value should readily undergo arylation. The DFT prediction was confirmed through experimental testing of nearly a dozen substrates containing activated C(sp3)-H bonds. This arylation method was also used in a one-pot protocol to synthesize over twenty compounds containing all-carbon quaternary centers.

Oxidative nucleophilic substitution of hydrogen in nitroarenes with phenylacetic acid derivatives

Oxidative nucleophilic substitution of hydrogen (ONSH) in nitroarenes with carbanion of isopropyl phenyl acetate gives various products depending on the conditions and oxidant. The reaction carried out in liquid ammonia and KMnO 4 oxidant gives

Oxidative nucleophilic substitution of hydrogen in nitroarenes with phenylacetonitrile derivatives

Tertiary carbanions generated from α-substituted phenylacetonitriles in liquid ammonia add to nitrobenzenes in the para position to form the corresponding σ(H)-adducts which are transformed, depending on the starting nitriles and the reaction conditions, to products of oxidative nucleophilic substitution of hydrogen, ONSH or vicarious nucleophilic substitution, VNS.

Kinetic and equilibrium studies of the proton and deuteron transfer reaction between diarylcyanomethanes and 1,2-bis(dialkylaminomethyl)benzene in acetonitrile

Equilibrium and rate constants, primary deuterium isotope effects, and activation parameters have been determined for the proton-transfer reactions of 4-nitrophenyl-phenylcyanomethane and 4-bromophenyl-4-nitrophenylcyanomethane with 1,2-bis(dimethylaminomethyl)benzene and 1,2-bis(diethylaminomethyl)benzene in acetonitrile.The reaction was followed spectrophotometrically using the stopped-flow technique.Large kinetic isotope effects at 25 deg C kH/kD = 16.8 - 18.8 were observed for studied reactions.The multistep mechanism of the reactions was proposed.

A NOVEL NUCLEOPHILIC SUBSTITUTION OF THE FORMYL GROUP IN p-NITROBENZALDEHYDE WITH SOME CARBANIONS

p-Nitrobenzaldehyde reacts with some active methylene compounds in the presence of a strong base at low temperatures to give p-substituted nitrobenzenes by the two-step course involving the initial formation of the aldol adducts and the subsequent displacement of the carbinol moieties with excess carbanions.

NUCLEOPHILIC SUBSTITUTION p-DINITROBENZENE WITH SOME CARBANIONS. FORMATION OF p-SUBSTITUTED NITROBENZENES

Treatment of p-dinitrobenzene with active methylene compounds of rather weak acidity in the presence of t-BuOK in liq NH3 at -70'C leads to nucleophilic substitution of a nitro group, giving p-substituted nitrobenzenes in generally good yields.

Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes with α-Substituted Nitriles and Esters. Direct α-Cyanoalkylation and α-Carbalkoxyalkylation of Nitroarenes

Carbanions generated from alkanenitriles bearing α-chloro, α-OR, or α-SR groups and from aliphatic esters bearing α-SR groups react with mononitroarenes to replace hydrogen atoms of the nitroaromatic ring ortho or para to the nitro group with α-cyanoalkyl or α-carbalkoxyalkyl substituents.The nucleophilic replacement of hydrogen with such carbanions proceeds faster than substitution of halogen ortho or para to the nitro group.

Vicarious Substitution of Hydrogen in Aromatic Nitro Compounds with Acetonitrile Derivatives

Carbanions of α-phenoxy and thioalkoxy nitriles substitute hydrogen in the para or ortho position of aromatic nitro compounds, giving nitroarylacetonitriles in a process in which phenolate or thiolate anions are vicarious leaving groups.