14368-40-2

Basic information

• Product Name: (2E)-3-phenylbut-2-enenitrile
• CAS NO: 14368-40-2
• Molecular Formula: C₁₀H₉N
• Molecular Weight: 143.1852
• Mol File: 14368-40-2.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 251.5°C at 760 mmHg
• Flash Point: 105.9°C
• Density: 0.996g/cm³
• Vapor Pressure: 0.0204mmHg at 25°C
• Refractive Index: 1.543
• CAS DataBase Reference: (2E)-3-phenylbut-2-enenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-phenylbut-2-enenitrile(14368-40-2)
• EPA Substance Registry System: (2E)-3-phenylbut-2-enenitrile(14368-40-2)

Safety Data

• Hazardous Substances Data: 14368-40-2(Hazardous Substances Data)

Usage

General Description

(2E)-3-phenylbut-2-enenitrile, also known as Cinnamyl cyanide, is a chemical compound with the molecular formula C10H9N. It is a yellow liquid with a faint almond-like odor, and is commonly used in the production of fragrances and flavorings. Cinnamyl cyanide is a nitrile compound, which means it contains a carbon-nitrogen triple bond. It is also used in the synthesis of pharmaceuticals and can act as a precursor to other organic compounds. However, it is important to note that cinnamyl cyanide is a toxic substance and should be handled with care in a controlled laboratory setting.

Upstream product

• 98-86-2 acetophenone 
• 590-17-0 cyanomethyl bromide 
• 107-14-2 chloroacetonitrile 
• 4593-90-2 3-phenylbutyric acid 
• 772-13-4 3-phenylbutanonamide 
• 20132-76-7 3-phenyl-butyronitrile 
• 1446698-46-9 (dimethylsilyl)acetonitrile 
• 75-05-8 acetonitrile 
• 4786-20-3 but-2-enenitrile 
• 71-43-2 benzene 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 120695-48-9 3-cyano-2-phenyl-1-N,N-dimethylamino-1-propene 
• 935-02-4 3-Phenyl-2-propynonitrile 
• 98-85-1 1-Phenylethanol 

Downstream Products

• 77434-68-5 (4-Benzyl-2-phenyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-acetonitrile 
• 14368-40-2 (Z)-3-phenylbut-2-enenitrile 
• 1196-67-4 (E)-β-methylcinnamaldehyde 
• 2031-46-1 (R)-3-phenylbutanol 
• 2031-46-1 (3S)-3-phenylbutan-1-ol 
• 211230-12-5 (S)-3-phenylbutyronitrile 

Relevant articles and documents

Wadsworth-Emmons reaction: The unique catalytic reaction by a solid base

The near-stoichiometric amount of bases is used both in laboratory and industry in Wadsworth-Emmons (WE) reactions, since the by-product, (EtO) 2P(O)OH, formed in the reaction neutralizes the base into an inert salt. A strategy to design, develop, and evolve the recyclable Mg-Al-hydrotalcite-OtBu (HT-OtBu) by the interaction of KOtBu with the calcined hydrotalcite that transforms a well-defined stoichiometric WE reaction into a catalytic one in an effort to minimize the quantum of effluents released and reduce the cost of the process is described here. HT-OtBu is found to be an efficient solid base for WE reactions for the simple synthesis of α,β-unsaturated esters and nitriles for the first time. The HT-OtBu, composed of various ratios of Mg/Al (i.e., 2, 2.5, and 3) and different contents of tBuO - (Mg/Al:3), and their precursors were prepared and well characterized to draw a correlation between structure and reactivity of the hydrotalcites in WE reactions.

Palladium(0)-catalyzed ring cleavage of cyclobutanone oximes leading to nitriles via β-carbon elimination [28]

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Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of thioacyl carbenes with alk-2-enals and mechanistic insights

A rhodium-catalyzed denitrogenative formal (3 + 3) transannulation of 1,2,3-thiadiazoles with alk-2-enals is achieved, producing 2,3-dihydrothiopyran-4-ones in moderate to excellent yields. An inverse KIE of 0.49 is obtained, suggesting the reversibility of the oxidative addition of thioacyl Rh(i) carbenes to alk-2-enals. The late-stage structural modifications of steroid compounds are realized. Moreover, our studies show that thioacyl carbenes have different reactivities to those of α-oxo and α-imino carbenes, and highlight the importance of heteroatoms in deciding the reactivities of heterovinyl carbenes.

Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes

The contra-thermodynamic isomerization of α- and β-substituted cinnamate derivatives catalyzed by the Cu(OAc)2/rac-BINAP complex under blue light irradiation is reported. The use of an oxazolidinone template, which favored the complexation of the copper catalyst to the substrate, allowed the E → Z isomerization of the catalytically formed chromophore under simple and robust reaction conditions in good to excellent ratios. The mechanism of this process based on the transient formation of a chromophore was also studied.