4043-71-4

Basic information

• Product Name: 5-[(E)-prop-1-enyl]benzo[1,3]dioxole
• Synonyms: 5-[(E)-prop-1-enyl]benzo[1,3]dioxole;TRANS-ISOSAFROLE;(E)-ISOSAFROLE;(E)-1-(1,3-Benzodioxole-5-yl)-1-propene;(E)-1-[3,4-(Methylenebisoxy)phenyl]propene;5-[(E)-1-Propenyl]-1,3-benzodioxole;(E)-5-(prop-1-en-1-yl)benzo[d][1,3]dioxole
• CAS NO: 4043-71-4
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 131.153
• Mol File: 4043-71-4.mol
• Article Data: 20

Chemical Properties

• Melting Point: 6.8°C
• Boiling Point: 253°C (estimate)
• Flash Point: 77.6°C
• Appearance: /
• Density: 1.1224
• Vapor Pressure: 0.26mmHg at 25°C
• Refractive Index: 1.5782 (estimate)
• CAS DataBase Reference: 5-[(E)-prop-1-enyl]benzo[1,3]dioxole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(E)-prop-1-enyl]benzo[1,3]dioxole(4043-71-4)
• EPA Substance Registry System: 5-[(E)-prop-1-enyl]benzo[1,3]dioxole(4043-71-4)

Safety Data

• Hazardous Substances Data: 4043-71-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H5NO2S/c1-5-2-3(6)8-4(5)7/h2H2,1H3

Upstream product

• 94-58-6 dihydrosafrole 
• 1135821-12-3 ethyl-(2-methoxy-phenyl)-diphenyl-phosphonium; iodide 
• 120-57-0 piperonal 
• 1135820-79-9 C₂₁H₂₂OP⁽¹⁺⁾*I^(1-) 
• 1135820-52-8 C₂₀H₂₀OP⁽¹⁺⁾*I^(1-) 
• 4736-60-1 ethyltriphenylphosphonium iodide 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 201230-82-2 carbon monoxide 
• 75-03-6 ethyl iodide 
• 67911-75-5 (E)-5-(3-bromoprop-1-en-1-yl)benzo[d][1,3]dioxole 
• 58095-76-4 (E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol 
• 24393-66-6 ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate 
• 64-19-7 acetic acid 
• 67-56-1 methanol 

Downstream Products

• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 821775-38-6 3-(3′,4′-methylenedioxophenyl)propenal 
• 16386-34-8 methyl 3-(3,4-dioxymethylenephenyl)propenoate 
• 1316653-57-2 1-(4-fluorophenyl)-5-(3,4-dimethoxymethylenephenyl)penta-2,4-dien-1-one 
• 1316653-51-6 1-(4-bromophenyl)-5-(3,4-dimethoxymethylenephenyl)penta-2,4-dien-1-one 
• 1316653-55-0 1-(4-chlorophenyl)-5-(3,4-dimethoxymethylenephenyl)penta-2,4-dien-1-one 
• 1316653-56-1 1-(3,4-dichlorophenyl)-5-(3,4-dimethoxymethylenephenyl)penta-2,4-dien-1-one 
• 14731-78-3 ethyl 3,4-methylenedioxycinnamate 
• 40918-96-5 methyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate 
• 58095-77-5 (E)-3,4-methylenedioxycinnamaldehyde 
• 4483-47-0 1β-ethyl-5,6-dimethoxy-3α-(3',4'-dimethoxyphenyl)-2β-methylindane 
• 28281-49-4 3,4-methylenedioxypropiophenone 

Relevant articles and documents

Iron Catalyzed Double Bond Isomerization: Evidence for an FeI/FeIII Catalytic Cycle

Iron-catalyzed isomerization of alkenes is reported using an iron(II) β-diketiminate pre-catalyst. The reaction proceeds with a catalytic amount of a hydride source, such as pinacol borane (HBpin) or ammonia borane (H3N?BH3). Reactivity with both allyl arenes and aliphatic alkenes has been studied. The catalytic mechanism was investigated by a variety of means, including deuteration studies, Density Functional Theory (DFT) and Electron Paramagnetic Resonance (EPR) spectroscopy. The data obtained support a pre-catalyst activation step that gives access to an η2-coordinated alkene FeI complex, followed by oxidative addition of the alkene to give an FeIII intermediate, which then undergoes reductive elimination to allow release of the isomerization product.

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.

Biphilic organophosphorus catalysis: Regioselective reductive transposition of allylic bromides via PIII/PV redox cycling

We report that a regioselective reductive transposition of primary allylic bromides is catalyzed by a biphilic organophosphorus (phosphetane) catalyst. Spectroscopic evidence supports the formation of a pentacoordinate (σ5-P) hydridophosphorane as a key reactive intermediate. Kinetics experiments and computational modeling are consistent with a unimolecular decomposition of the σ5-P hydridophosphorane via a concerted cyclic transition structure that delivers the observed allylic transposition and completes a novel PIII/PV redox catalytic cycle. These results broaden the growing repertoire of reactions catalyzed within the PIII/PV redox couple and suggest additional opportunities for organophosphorus catalysis in a biphilic mode.