51003-16-8

Basic information

• Product Name: 5-[(Z)-2-phenylethenyl]-1,3-benzodioxole
• CAS NO: 51003-16-8
• Molecular Formula: C₁₅H₁₂O₂
• Molecular Weight: 224.2546
• Mol File: 51003-16-8.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 353°C at 760 mmHg
• Flash Point: 172.3°C
• Density: 1.219g/cm³
• Vapor Pressure: 7.54E-05mmHg at 25°C
• Refractive Index: 1.684
• CAS DataBase Reference: 5-[(Z)-2-phenylethenyl]-1,3-benzodioxole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(Z)-2-phenylethenyl]-1,3-benzodioxole(51003-16-8)
• EPA Substance Registry System: 5-[(Z)-2-phenylethenyl]-1,3-benzodioxole(51003-16-8)

Safety Data

• Hazardous Substances Data: 51003-16-8(Hazardous Substances Data)

Upstream product

• 103-82-2 phenylacetic acid 
• 120-57-0 piperonal 
• 100-42-5 styrene 
• 7228-38-8 5-chloro-1,3-benzodioxole 
• 957768-42-2 (3,4-methylenedioxy-phenyl)phenylacetylene 
• 495-76-1 piperonol 
• 140-29-4 phenylacetonitrile 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 42599-24-6 E-styryl iodide 
• 3112-88-7 Benzyl phenyl sulfone 
• 7016-55-9 benzyl-triethylphosphonium bromide 
• 1266707-81-6 C₂₁H₁₈O₂S 
• 591-50-4 iodobenzene 
• 2065-66-9 methyl-triphenylphosphonium iodide 

Downstream Products

• 54225-86-4 (3,4-methylenedioxyphenyl) phenyl methanone 
• 100461-31-2 5-(α,β-dibromo-phenethyl)-benzo[1,3]dioxole 
• 40804-81-7 2-(benzo[d][1,3]dioxol-5-yl)-1-phenylethan-1-one 
• 179397-86-5 2-(3,4-methylenedioxyphenyl)-1-phenylethanamine 

Relevant articles and documents

Dinuclear cobalt complex-catalyzed stereodivergent semireduction of alkynes: Switchable selectivities controlled by H2O

Catalytic semireduction of internal alkynes to alkenes is very important for organic synthesis. Although great success has been achieved in this area, switchable Z/E stereoselectivity based on a single catalyst for the semireduction of internal alkynes is a longstanding challenge due to the multichemo- and stereoselectivity, especially based on less-expensive earth-abundant metals. Herein, we describe a switchable semireduction of alkynes to (Z)- or (E)-alkenes catalyzed by a dinuclear cobalt complex supported by a macrocyclic bis pyridyl diimine (PDI) ligand. It was found that cis-reduction of the alkyne occurs first and the Z-E alkene stereoisomerization process is formally controlled by the amount of H2O, since the concentration of H2O may influence the catalytic activity of the catalyst for isomerization. Therefore, this protocol provides a facile way to switch to either the (Z)- or (E)-olefin isomer in a single transformation by adjusting the amount of water.

Stereospecific Iron-Catalyzed Carbon (sp2)-Carbon (sp2) Cross-Coupling of Aryllithium with Vinyl Halides

We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed.

Wittig Reactions of Trialkylphosphine-derived Ylides: New Directions and Applications in Organic Synthesis

The development of semi-stabilized, stabilized, and functionalized ylides derived from short-chain trialkylphosphines in the Wittig-type olefination reactions toward the synthesis of alkenes, including stilbenes, styrenes, and 1,3-dienes, as well as reagents for homologation reactions, are described. The methods allow easy access to alkenes with high (E)-stereoselectivity in good yield. These reactions are conducted with weak bases in aqueous media, which allows easy separation of water-soluble phosphine oxides. The development of a mild organocatalytic process for the Wittig reaction and extension toward the preparation of reporter stilbenes under biological conditions are also described. Applications toward the preparation of biologically active natural products and derivatives are discussed.