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
• Article Data: 60

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

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 16958-42-2 but-3-en-1-yltriphenylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 107-05-1 3-chloroprop-1-ene 
• 201852-49-5 potassium (E)-trifluoro(styryl)borate 
• 7214-53-1 (E)-[2-(phenylsulfanyl)vinyl]benzene 
• 82934-96-1 Allylzinc chloride 
• 124447-29-6 4-nitrophenyl 2-phenylethenyl sulfide 
• 28557-00-8 phenylzinc chloride 
• 119441-89-3 (E)-(2-bromoethenyl)diisopropoxyborane 
• 106-95-6 allyl bromide 
• 24850-33-7 allyltributylstanane 
• 1826-67-1 vinyl magnesium bromide 

Downstream Products

• 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 

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.

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.

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.