28446-70-0

Basic information

• Product Name: p-methylcinnamonitrile
• Synonyms: p-methylcinnamonitrile;3-(4-Methylphenyl)acrylonitrile;3-(4-Methylphenyl)propenenitrile
• CAS NO: 28446-70-0
• Molecular Formula: C₁₀H₉N
• Molecular Weight: 143.18516
• EINECS: 249-024-5
• Mol File: 28446-70-0.mol
• Article Data: 94

Chemical Properties

• Boiling Point: 269.8°Cat760mmHg
• Flash Point: 117.2°C
• Appearance: /
• Density: 1.022g/cm³
• Vapor Pressure: 0.00709mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: p-methylcinnamonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: p-methylcinnamonitrile(28446-70-0)
• EPA Substance Registry System: p-methylcinnamonitrile(28446-70-0)

Safety Data

• Hazardous Substances Data: 28446-70-0(Hazardous Substances Data)

Usage

General Description

p-Methylcinnamonitrile, also known as 3-(4-methylphenyl)propionitrile, is a chemical compound that belongs to the class of organic compounds known as phenylpropanes. It is commonly used in the synthesis of fragrances and flavors due to its sweet, balsamic, and slightly floral aroma. It is also used as an intermediate in the production of pharmaceuticals and agricultural chemicals. p-Methylcinnamonitrile is a colorless to pale yellow liquid with a boiling point of 270°C and a molecular formula of C10H9N. It is important to handle this chemical with caution as it can be irritating to the skin, eyes, and respiratory system.

InChI:InChI=1/C10H9N/c1-9-4-6-10(7-5-9)3-2-8-11/h2-7H,1H3/b3-2+

Upstream product

• 4224-87-7 4-methyl-chalcone 
• 75-05-8 acetonitrile 
• 80540-68-7 2-cyano-3-(p-tolyl)acrylic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 3395-83-3 4-methylbenzaldehyde dimethylacetal 
• 2362-77-8 (4-methylbenzylidene)phenylamine 
• 93626-87-0 3-p-tolylprop-2-enal phenylhydrazone 
• 75159-10-3 N-(4-methylbenzylidene)-p-toluenesulfonamide 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 106-38-7 para-bromotoluene 
• 107-13-1 acrylonitrile 
• 624-31-7 4-tolyl iodide 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 4073-48-7 3-(4-methylphenyl)-3-phenylpropanenitrile 
• 2286-54-6 3,3-diphenyl-propionitrile 
• 4073-52-3 3-(4-methylphenyl)-3-phenylpropan-1-amine 
• 5586-73-2 3-diphenylpropyl amine 
• 54930-39-1 3-(4-methylphenyl)propanamine 
• 32327-69-8 1-cyano-2-(4'-methylphenyl)ethane 

Relevant articles and documents

Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide

A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is

Pd(II)-Catalyzed CC Bond Cleavage by a Formal Group-Exchange Reaction

A chelation-assisted palladium-catalyzed CC bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1C2 + C3 → C1C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity of the chelation group, and a plausible catalytic pathway was proposed.

Cu-catalyzed cyanomethylation of imines and α,β-alkenes with acetonitrile and its derivatives

We describe copper-catalyzed cyanomethylation of imines and α,β-alkenes with a methylnitrile source and provide an efficient route to synthesize arylacrylonitriles and β,γ-unsaturated nitriles. This method tolerates aliphatic and aromatic alkenes substituted with a variety of functional groups such as F, Cl, Br, Me, OMe,tert-Bu, NO2, NH2and CO2H with good to excellent yields (69-98%). These systems consist of inexpensive, simple copper catalyst and acetonitrile with its derivatives (α-bromo/α-iodo-acetonitrile) and are highly applicable in the industrial production of acrylonitriles.