55666-17-6

Basic information

• Product Name: Benzene, (1E)-1,4-pentadienyl-
• Synonyms: ((E)-Penta-1,4-dienyl)-benzene;(E)-penta-1,4-diene-1-ylbenzene;(E)-penta-1,4-dien-1-ylbenzene;trans-1-phenylpenta-1,4-diene;trans-1-phenyl-1,4-pentadiene;(1E)-penta-1,4-dienylbenzene;(E)-penta-1,4-dien-1-yl benzene
• CAS NO: 55666-17-6
• Molecular Formula: C11H12
• Molecular Weight: 144.216
• Mol File: 55666-17-6.mol

Chemical Properties

• Boiling Point: 96.5 - 97 °C (13 mmHg)
• Density: 0.909±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzene, (1E)-1,4-pentadienyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (1E)-1,4-pentadienyl-(55666-17-6)
• EPA Substance Registry System: Benzene, (1E)-1,4-pentadienyl-(55666-17-6)

Safety Data

• Hazardous Substances Data: 55666-17-6(Hazardous Substances Data)

Upstream product

• 30094-01-0 β-styrylmagnesium bromide 
• 106-95-6 allyl bromide 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 112176-14-4 CH₂CHTi(N(C₂H₅)2)3 
• 4392-24-9 Cinnamyl bromide 
• 556-56-9 allyl iodid 
• 103-64-0 bromostyrene 
• 2622-05-1 allylmagnesium bromide 
• 1826-67-1 vinyl magnesium bromide 
• 51498-40-9 trans-N,N-dimethyl-5-phenyl-4-penten-1-amine 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 24857-04-3 triethylallyltin 
• 17421-58-8 trans-(C₂H₅)3SnCHCHC₆H₅ 

Downstream Products

• 54985-34-1 trans-1-phenyl-1-penten-3-ol 
• 102632-99-5 1-phenyl-4-penten-1-ol 
• 198642-79-4 (2S)-1-phenylpentan-2-ol 
• 1610026-40-8 4-phenyl-1-((2E,4E)-5-phenylpenta-2,4-dienyl)-1H-1,2,3-triazole 
• 1613403-63-6 (2E,4E,6E)-methyl 2,7-diphenylhepta-2,4,6-trienoate 
• 3152-68-9 (1E)-1-phenylpent-1-en-3-one 
• 58506-33-5 5-phenyl-trans,trans-2,4-pentadien-1-ol 

Relevant articles and documents

Rhodium-catalyzed allylation of styrenes with allyl tosylate

Rhodium-catalyzed allylation of styrene with allyl tosylate gave 1-phenylpenta-1,4-diene, and various styrene derivatives were also allylated yielding 1,4-dienes or 1,5-dienes.

The Reactions of Copper(I) 1-Alkenyltrimethylborates with Allylic Bromides or 2-Propynyl Bromide

The reactions between copper(I) 1-alkenyltrimethylborates ( readily obtainable from 2-(1-alkenyl)-1,3,2-benzodioxaboroles and methyllithium) and allylic bromides or 2-propynyl bromide were found to give corresponding coupling products.These reactions provide new synthetic routes to 1,4-alkadienes or 1,2,7-alkatrien-5-ynes.

C–C Cross-Coupling Reactions of Organosilanes with Terminal Alkenes and Allylic Acetates Using PdII Catalyst Supported on Starch Coated Magnetic Nanoparticles

Starch coated magnetic nanoparticles supported palladium catalyst has been explored to perform C–C cross coupling reactions, such as oxidative Heck coupling and Tsuji–Trost allylic coupling using organosilicon compounds as one of the coupling partners. The biopolymer coated magnetic catalyst was very easy to recover magnetically and was efficiently recycled in the subsequent batches. All the reactions were performed in air and thus the necessity of air and moisture free reaction condition is avoided. The present protocols show wide substrate scope and good yields of the products.

Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C-O bond cleavage was performed. Reaction of (E)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (E)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted (E)-(prop-1-ene-1,3-diyl)dibenzenes or 3-aryl/alkenyl-substituted (E)-(but-1-enyl)benzene. Reaction of allyl alcohol with p-Me2NC6H4ZnCl resulted in a mixture of normal coupling product 4-allyl-N,N-dimethylaniline and its isomerized product N,N-dimethyl-4-(prop-1-en-1-yl)aniline.

Chemo- and regioselective reductive transposition of allylic alcohol derivatives via iridium or rhodium catalysis

We report highly chemo- and regioselective reductive transpositions of methyl carbonates to furnish olefin products with complementary regioselectivity to that of established Pd-catalysis. These Rh- and Ir-catalysed transformations proceed under mild conditions and enable selective deoxygenation in the presence of functional groups that are susceptible to reduction by metal hydrides.

Copper(I)-Catalyzed Allylic Substitutions with a Hydride Nucleophile

An easily accessible copper(I)/N-heterocyclic carbene (NHC) complex enables a regioselective hydride transfer to allylic bromides, an allylic reduction. The resulting aryl- and alkyl-substituted branched α-olefins, which are valuable building blocks for synthesis, are obtained in good yields and regioselectivity. A commercially available silane, (TMSO)2Si(Me)H, is employed as hydride source. This protocol offers a unified alternative to the established metal-catalyzed allylic substitutions with carbon nucleophiles, as no adaption of the catalyst to the nature of the nucleophile is required.

Ligand Control of E/Z Selectivity in Nickel-Catalyzed Transfer Hydrogenative Alkyne Semireduction

A nickel-catalyzed transfer hydrogenative alkyne semireduction protocol that can be applied to both internal and terminal alkynes using formic acid and Zn as the terminal reductants has been developed. In the case of internal alkynes, the (E)- or (Z)-olefin isomer can be accessed selectively under the same reaction conditions by judicious inclusion of a triphos ligand.

Direct conversion of allyl arenes to aryl ethylketones via a TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes

A TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes was developed. This methodology provides a new efficient and simple route for conversion of a range of allyl arenes directly into aryl ethylketones in good yields with high chemoselectivity.

Stereoretentive Pd-catalyzed kumada-corriu couplings of alkenyl halides at room temperature

Stereoselective palladium-catalyzed Kumada-Corriu reactions of functionalized alkenyl halides and a variety of Grignard reagents, including those bearing β-hydrogen atoms and sensitive functional groups, can be carried out at room temperature using a new combination of reagents.

Palladium-catalyzed regioselective azidation of allylic C-H bonds under atmospheric pressure of dioxygen

A palladium-catalyzed allylic azidation of alkenes with sodium azide under atmospheric pressure of dioxygen was developed. This methodology provides a new efficient and simple route for accessing allylic azides. Furthermore, the one-pot process consisting of Pd-catalyzed allylic azidation of alkenes and Cu-catalyzed 1,3-dipolar cycloaddition led directly to the 1,2,3-triazole from the alkene. The formed allylic azide can be also in situ reduced to the allylic amine or oxidized to the alkenyl nitrile. the Partner Organisations 2014.