10340-49-5

Basic information

• Product Name: 4-Phenyl-1-pentene
• Synonyms: (1-Methyl-3-butenyl)benzene;4-Phenyl-1-pentene
• CAS NO: 10340-49-5
• Molecular Formula: C11H14
• Molecular Weight: 146.23
• Mol File: 10340-49-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Phenyl-1-pentene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenyl-1-pentene(10340-49-5)
• EPA Substance Registry System: 4-Phenyl-1-pentene(10340-49-5)

Safety Data

• Hazardous Substances Data: 10340-49-5(Hazardous Substances Data)

Usage

Uses

Used in Polymer and Plastics Industry:
4-Phenyl-1-pentene is used as a monomer in the production of polymers and plastics, contributing to the development of materials with specific properties tailored for various applications.
Used in Chemical Synthesis:
4-Phenyl-1-pentene is utilized as an intermediate in the synthesis of other organic compounds, playing a crucial role in the creation of a wide range of chemical products.
Used as a Solvent:
In various chemical processes, 4-Phenyl-1-pentene is employed as a solvent, facilitating reactions and aiding in the dissolution of substances for further processing or analysis.
Safety Precautions:
Due to its flammable properties, 4-Phenyl-1-pentene requires careful handling and storage to prevent accidents and ensure the safety of personnel and equipment. Proper safety measures, including the use of protective equipment and adherence to safety protocols, are essential when working with this compound.

Upstream product

• 100-42-5 styrene 
• 2622-05-1 allylmagnesium bromide 
• 593-60-2 Vinyl bromide 
• 124-38-9 carbon dioxide 
• 78330-52-6 2-phenylpropylmagnesium chloride 
• 34713-70-7 2-Phenylpropanal 
• 1826-67-1 vinyl magnesium bromide 
• 79981-29-6 (1S,2S)-2-phenylcyclopropylmethyl acetate 
• 75-24-1 trimethylaluminum 
• 81194-44-7 dimethylallylsilyl 1-phenylethyl ether 
• 672-65-1 (1-chloroethyl)benzene 
• 762-72-1 allyl-trimethyl-silane 
• 585-71-7 (1-bromoethyl)benzne 
• 60779-09-1 1-phenylethylmagnesium chloride 

Downstream Products

• 57094-30-1 2-methyl-4-phenylpentanal 
• 127047-11-4 5-phenylhexanal 
• 42461-65-4 (E)-(pent-3-en-2-yl)benzene 
• 76807-04-0 (Z)-(pent-3-en-2-yl)benzene 
• 1067187-85-2 1-hydroxy-4-phenylpentan-2-one 
• 17913-10-9 1-methyl-3-phenyl-butanal 
• 32587-80-7 (S)-4-phenylpentan-2-one 
• 67110-72-9 (4R)-4-phenylpentan-2-one 
• 70303-28-5 (E)-pent-2-en-2-ylbenzene 

Relevant articles and documents

Bismuth(III) chloride-catalyzed direct deoxygenative allylation of substituted benzylic alcohols with allyltrimethylsilane

A highly effective protocol for allylation of sec-benzyl alcohols with allyltrimethylsilane in the presence of a catalytic amount of bismuth(III) chloride has been developed.

Indium-silicon combined Lewis acid catalyst for direct allylation of alcohols with allyltrimethylsilane in non-halogenated solvent

A direct allylation of alcohols is effectively catalyzed by a combined Lewis acid system of InCl3 and Me3SiBr. This system allows use of non-halogenated solvents such as hexane and application to a wide range of alcohols. Georg Thieme Verlag Stuttgart.

Palladium-Catalyzed Electrochemical Allylic Alkylation between Alkyl and Allylic Halides in Aqueous Solution

A new route for the direct cross-coupling of alkyl and allylic halides using electrochemical technique has been developed in aqueous media under air. Catalyzed by Pd(OAc)2, the Zn-mediated allylic alkylations proceed smoothly between a full range of alkyl halides (primary, secondary, and tertiary) and substituted allylic halides. Protection-deprotection of acidic hydrogen in the substrates is avoided.

Silylated cyclopentadienes as competent silicon Lewis acid catalysts

The synthesis and characterization of silicon Lewis acid complexes that incorporate highly electron-deficient cyclopentadienes is reported. Several pentacarboxycyclopentadienyl and monocarboxytetracyanocyclopentadienyl complexes were prepared. A comparison of their reactivities for catalysis of the allylation of an electron-deficient benzaldehyde was established. The use of a monocarboxytetracyano silylium donor was shown to be effective for the allylation or arylation of a variety of electrophiles via an anion abstraction pathway.

CROSS-COUPLING REACTION OF SECONDARY ALKYL GRIGNARD REAGENTS WITH ALLYLIC ALCOHOLS CATALYZED BY DICHLOROPALLADIUM(II)

Dichloropalladium(II) was found to catalyze the reaction of allylic alcohols with 2-octylmagnesium chloride and 1-phenylethylmagnesium chloride to give the corresponding cross-coupling products in high yields.

Efficient and mild iron-catalyzed direct allylation of benzyl alcohols and benzyl halides with allyltrimethylsilane

An efficient and mild iron-catalyzed direct allylation of benzyl alcohols and benzyl halides with allyltrimethylsilane has been developed. The present reaction would provide an excellent alternative to published methods because of its excellent yields, sustainable catalyst, and mild conditions. Copyright Taylor & Francis Group, LLC.

Designed electron-deficient gold nanoparticles for a room-temperature Csp3-Csp3coupling reaction

Stille cross-coupling reactions catalysed by an ideal catalyst combining the high activity of homogeneous catalysts and the reusability of heterogeneous catalysts are of great interest for C-C bond formation, which is a widely used reaction in fine chemistry. Despite great effort to increase the utilization ratio of surface metal atoms, the activity of heterogeneous catalysts under mild conditions remains unsatisfactory. Herein, we design a proof-of-concept strategy to trigger the room-temperature activity of heterogeneous Au catalysts by decreasing the electron density at the interface of a rationally designed Schottky heterojunction of Au metals and boron-doped carbons. The electron-deficient Au nanoparticles formed as a result of the rectifying contact with boron-doped carbons facilitate the autocleavage of C-Br bonds for highly efficient C-C coupling reactions of alkylbromides and allylstannanes with a TOF value of 5199 h-1 at room temperature, surpassing that of the state-of-the-art homogeneous catalyst. This journal is

Visible-Light Controlled Divergent Catalysis Using a Bench-Stable Cobalt(I) Hydride Complex

While the use of visible light in conjunction with transition metal catalysis offers powerful opportunities to switch between on/-off states of catalytic activity, the next frontier would be the ability to switch the actual function of the catalyst and resulting products. Here we report such an example of multi-dimensional catalysis. Featuring an easily prepared, bench-stable cobalt(I) hydride complex in conjunction with pinacolborane, we can switch the reaction outcome between two widely employed transformations, olefin migration and hydroboration, with visible light as the trigger.

In Situ Generated Gold Nanoparticles on Active Carbon as Reusable Highly Efficient Catalysts for a Csp3 ?Csp3 Stille Coupling

Gold nanoparticle catalysts are important in many industrial production processes. Nevertheless, for traditional Csp2-Csp2 cross-coupling reactions they have been rarely used and Pd catalysts usually give a superior performance. Herein we report that in situ formed gold metal nanoparticles are highly active catalysts for the cross coupling of allylstannanes and activated alkylbromides to form Csp3-Csp3 bonds. Turnover numbers up to 29 000 could be achieved in the presence of active carbon as solid support, which allowed for convenient catalyst recovery and reuse. The present study is a rare case where a gold metal catalyst is superior to Pd catalysts in a cross-coupling reaction of an organic halide and an organometallic reagent.

(CDC)-Rhodium-catalyzed hydroallylation of vinylarenes and 1,3-dienes with allyltrifluoroborates

Catalytic site-selective hydroallylation of vinyl arenes and 1,3-dienes is reported. Transformations are promoted by a readily accessible bidentate carbodicarbene-rhodium complex and involve commercially available allyltrifluoroborates and an alcohol. The reaction is applicable to vinyl arenes and aryl-or alkyl-substituted 1,3-dienes (30 examples). Allyl addition products are generated in 40-78% yield and in up to >98:2 site selectivity. Reaction outcomes are consistent with the intermediacy of a Rh(III)-hydride generated by protonation of Rh(I) by an acid. A number of key mechanistic details of the reaction are presented: (1) Deuterium scrambling into the product and starting alkene indicates reversible Rh(III)-H migratory insertion. (2) A large primary kinetic isotope effect is observed. (3) With substituted allyltrifluoroborates (e.g., crotyl-BF3K) mixtures of site isomers are generated as a result of transmetalation followed by Rh-(allyl) complex equilibration, consequently disproving outer-sphere addition of the allyl nucleophile to Rh(III)-(η3-allyl). (4) Stereochemical analysis of a cyclohexadiene allyl addition product supports a syn Rh(III)-hydride addition. (5) A Hammett plot shows a negative slope. Finally, utility is highlighted by a iodocyclization and cross metathesis.