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

• 495-76-1 piperonol 
• 3112-88-7 Benzyl phenyl sulfone 
• 957768-42-2 (3,4-methylenedioxy-phenyl)phenylacetylene 
• 100-42-5 styrene 
• 7228-38-8 5-chloro-1,3-benzodioxole 
• 120-57-0 piperonal 
• 1589-82-8 phenylmagnesium bromide 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 7016-55-9 benzyl-triethylphosphonium bromide 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 7315-32-4 5-vinyl-1,3-benzodioxole 
• 591-50-4 iodobenzene 
• 76306-61-1 N-(2-benzo[1,3]dioxol-5-yl-1-phenyl-ethyl)-acetamide 
• 130014-33-4 Benzyl-(2-hydroxy-ethyl)-diphenyl-arsonium; bromide 

Downstream Products

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

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.

Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.

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.