51557-09-6

Basic information

• Product Name: (E)-4-(1-naphthyl)-3-buten-2-one
• Synonyms: (E)-4-(1-naphthyl)-3-buten-2-one;(E)-4-(1-Naphthalenyl)-3-buten-2-one;(E)-4-(1-Naphtyl)-3-butene-2-one;Methyl[(E)-2-(1-naphtyl)ethenyl] ketone;Einecs 257-285-1
• CAS NO: 51557-09-6
• Molecular Formula: C₁₄H₁₂O
• Molecular Weight: 196.24448
• EINECS: 257-285-1
• Mol File: 51557-09-6.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 370°C at 760 mmHg
• Flash Point: 140.7°C
• Appearance: /
• Density: 1.101g/cm³
• Vapor Pressure: 1.14E-05mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: (E)-4-(1-naphthyl)-3-buten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(1-naphthyl)-3-buten-2-one(51557-09-6)
• EPA Substance Registry System: (E)-4-(1-naphthyl)-3-buten-2-one(51557-09-6)

Safety Data

• Hazardous Substances Data: 51557-09-6(Hazardous Substances Data)

Usage

Description

(E)-4-(1-naphthyl)-3-buten-2-one, also known as 1-Naphthalen-1-yl-3-buten-2-one, is an aromatic chemical compound characterized by a naphthalene core and a butenone side chain. It is utilized in various chemical processes and industrial applications due to its unique structure and properties.

Uses

Used in Pharmaceutical Synthesis:
(E)-4-(1-naphthyl)-3-buten-2-one is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Synthesis:
In the agrochemical industry, (E)-4-(1-naphthyl)-3-buten-2-one is used as a key component in the synthesis of various agrochemicals, such as pesticides and fertilizers, to enhance agricultural productivity and crop protection.
Used in Organic Compound Synthesis:
(E)-4-(1-naphthyl)-3-buten-2-one is also employed in the synthesis of other organic compounds, expanding its utility in the chemical industry and contributing to the creation of a diverse range of products.
Used in Biological Applications:
(E)-4-(1-naphthyl)-3-buten-2-one exhibits biological activities, such as anti-inflammatory and anti-tumor properties, making it a potential candidate for research and development in the field of medicine.
Safety Precautions:
It is crucial to handle (E)-4-(1-naphthyl)-3-buten-2-one with care, as it may pose health risks if ingested, inhaled, or comes into contact with the skin. Adequate safety measures and protocols should be followed to ensure the safe handling and use of this compound in various applications.

InChI:InChI=1/C14H12O/c1-11(15)9-10-13-7-4-6-12-5-2-3-8-14(12)13/h2-10H,1H3/b10-9+

Upstream product

• 66-77-3 1-naphthaldehyde 
• 67-64-1 acetone 
• 1423-60-5 methyl ethynyl ketone 
• 166328-07-0 potassium trifluoro(naphth-1-yl)borate 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 90-11-9 1-Bromonaphthalene 
• 78-94-4 methyl vinyl ketone 
• 876-27-7 4-chlorophenyl acetate 
• 66920-76-1 (3E)-4-(naphthalen-1-yl)but-3-en-2-ol 

Downstream Products

• 1620238-67-6 C₃₁H₂₈O₅ 
• 1357560-58-7 6-methyl-4-(naphthalen-1-yl)-2,3-diphenylpyridine 
• 3506-84-1 4-(1-naphthyl)-2-butanone 
• 66920-76-1 (3E)-4-(naphthalen-1-yl)but-3-en-2-ol 
• 66920-78-3 4-(naphthalen-1-yl)butan-2-ol 
• 187404-47-3 (R)-2-[1-phenyl-(E)-methylidene]-1-cyclohexanol 
• 187404-39-3 (S)-2-[1-phenyl-(E)-methylidene]-1-cyclohexanol 

Relevant articles and documents

Relay Catalysis to Synthesize β-Substituted Enones: Organocatalytic Substitution of Vinylogous Esters and Amides with Organoboronates

Organocatalysis was shown to facilitate conjugate additions to vinylogous esters and amides for the first time. Subsequent elimination of a β-alcohol or amine provided π-conjugated β-substituted enones. Remarkably, nucleophile addition to the electron-rich vinylogous substrates is more rapid than classical enones, forming monosubstituted products. A doubly organocatalytic (organic diol and methyl aniline) conjugate addition synthesized the products directly from alkynyl ketones. Both of these catalytic transformations are orthogonal to transition metal catalysis, allowing for good yields, easily accessible or commercially available reagents, high selectivity, reagent recovery and recyclability, facile scalability, and exceptional functional group tolerance.

Organoselenium-catalyzed baeyer-villiger oxidation of α,β-unsaturated ketones by hydrogen peroxide to access vinyl esters

By carefully screening the organoselenium pre-catalysts and optimizing the reaction conditions, simple dibenzyl diselenide was found to be the best pre-catalyst for Baeyer-Villiger oxidation of (E)-α,β-unsaturated ketones with the green oxidant hydrogen peroxide at room temperature. The organoselenium catalyst used in this reaction could be recycled and reused several times. This new method was suitable not only for methyl unsaturated ketones, but also for alkyl and aryl unsaturated ketones. Therefore, it provided a direct, mild, practical, highly functional group-tolerant process for the chemoselective preparation of the versatile (E)-vinyl esters from the readily available (E)-α,β-unsaturated ketones. A possible mechanism was also proposed to rationalize the activity of the organoselenium catalyst in the presence of hydrogen peroxide in this Baeyer-Villiger oxidation reaction.

Preparation of monometallic (Pd, Ag) and bimetallic (Pd/Ag, Pd/Ni, Pd/Cu) nanoparticles via reversed micelles and their use in the Heck reaction

The metal nanoparticles (NPs) have been prepared using a water-in-oil microemulsion system of water/dioctyl sulfosuccinate sodium salt (aerosol-OT, AOT)/isooctane at 25 °C. Since the NPs produced in this system can endure forcing conditions (100 °C), this system has been used for the synthesis of nano-catalysts in the Heck reactions. FE-SEM, DLS, and UV/vis analyses have been used to characterize the surface morphology, size, and proof of the formation of all the prepared metal NPs, respectively. In addition, the effects of some reaction parameters (here, bases and solvents) were optimized. Differences in the catalytic properties of the synthesized NPs have also been investigated. Consequently, the Pd/Cu (4:1) bimetallic NP showed the highest activity in the C-C coupling reaction of the iodobenzene with the styrene, thus it is employed as the superior catalyst in this study. Therefore, the Pd/Cu (4:1) bimetallic NPs were further investigated using TEM and XRD analyses. This catalyst system is also reusable for six runs with very negligible reduction in the efficiency.