14756-00-4

Basic information

• Product Name: 3-(1,3-benzodioxol-5-yl)acrylaldehyde
• Synonyms: 3-(1,3-benzodioxol-5-yl)acrylaldehyde;3,4-(METHYLENEDIOXY)CINNAMALDEHYDE;1,3-Benzodioxole-5-acrolein;1,3-Benzodioxole-5-acrylaldehyde;3-(1,3-Benzodioxol-5-yl)-2-propenal;3-(1,3-Benzodioxole-5-yl)acrylaldehyde;3-(3,4-Methylenedioxyphenyl)propenal;Nsc23868
• CAS NO: 14756-00-4
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.16872
• EINECS: 238-816-6
• Mol File: 14756-00-4.mol
• Article Data: 29

Chemical Properties

• Melting Point: 84-85 °C(Solv: ethanol (64-17-5))
• Boiling Point: 326.3°Cat760mmHg
• Flash Point: 142.2°C
• Appearance: /
• Density: 1.268g/cm³
• Vapor Pressure: 0.000218mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 3-(1,3-benzodioxol-5-yl)acrylaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1,3-benzodioxol-5-yl)acrylaldehyde(14756-00-4)
• EPA Substance Registry System: 3-(1,3-benzodioxol-5-yl)acrylaldehyde(14756-00-4)

Safety Data

• Hazardous Substances Data: 14756-00-4(Hazardous Substances Data)

Usage

General Description

3-(1,3-benzodioxol-5-yl)acrylaldehyde is a chemical compound with the molecular formula C10H8O3. It is a yellow-colored liquid with a fruity odor, and it is primarily used as an intermediate in the production of various pharmaceuticals and organic compounds. 3-(1,3-benzodioxol-5-yl)acrylaldehyde is also used in the synthesis of fine chemicals and as a reagent in organic chemical reactions. It is important to handle 3-(1,3-benzodioxol-5-yl)acrylaldehyde with caution, as it is considered toxic if ingested or inhaled. It is also a skin and eye irritant, and prolonged exposure should be avoided. Additionally, it is important to store this chemical in a cool, dry place away from incompatible materials and sources of ignition.

InChI:InChI=1/C10H8O3/c11-5-1-2-8-3-4-9-10(6-8)13-7-12-9/h1-6H,7H2/b2-1+

Upstream product

• 94-58-6 dihydrosafrole 
• 7031-03-0 3-(benzo[d][1,3]dioxol-5-yl)propan-1-ol 
• 495-76-1 piperonol 
• 120-57-0 piperonal 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 27064-04-6 S-(4-nitrophenyl) thioformate 
• 121-44-8 triethylamine 
• 5208-87-7 1'-hydroxysafrole 
• 2620-47-5 1-(benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol 
• 1612873-28-5 (E)-1-(benzo[d][1,3]dioxol-6-yl)-3-(dimethyl(phenyl)silyl)prop-2-en-1-ol 
• 4043-71-4 isosafrole 
• 123261-70-1 (E)-5-(3,3-diethoxy-1-propenyl)-1,3-benzodioxole 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 

Downstream Products

• 1339075-22-7 diethyl (1-(benzo[d][1,3]dioxol-5-yl)-3-(n-(benzyloxy)acetamido)propyl)phosphonate 
• 495-85-2 (+/-)-methysticin 
• 24393-66-6 ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate 

Relevant articles and documents

Three-component synthesis of (E)-α,β-unsaturated amides of the piperine family

Selective formation of (E)-α,β-unsaturated amides by intermolecular three-component reaction between aldehydes, amines (1° or 2°) and ketenylidenetriphenylphosphorane (Ph3P=C=C=O) is described. Natural amides such as fagaramide and piperines could be prepared from immediately available educts. The method is shown to be extendable to the preparation of thioesters from thiols and aldehydes.

Tandem oxidation-dehydrogenation of (hetero)arylated primary alcohols via perruthenate catalysis

Tandem oxidative-dehydrogenation of primary alcohols to give a,b-unsaturated aldehydes in one pot are rare transformations in organic synthesis, with only two methods currently available. Reported herein is a novel method using the bench-stable salt methyltriphenylphosphonium perruthenate (MTP3), and a new co-oxidant NEMO&middoPF6 (NEMO = N-ethyl-N-hydroxymorpholinium) which provides unsaturated aldehydes in low to moderate yields. The Ley-Griffith oxidation of (hetero)arylated primary alcohols with N-oxide co-oxidants NMO (NMO = N-methylmorpholine N-oxide)/NEMO, is expanded by addition of the N-oxide salt NEMO&middoPF6 to convert the intermediate saturated aldehyde into its unsaturated counterpart. The discovery, method development, reaction scope, and associated challenges of this method are highlighted. The conceptual value of late-stage dehydrogenation in natural product synthesis is demonstrated via the synthesis of a polyene scaffold related to auxarconjugatin B.

Design of novel monoamine oxidase-B inhibitors based on piperine scaffold: Structure-activity-toxicity, drug-likeness and efflux transport studies

Piperine has been associated with neuroprotective effects and monoamine oxidase (MAO) inhibition, thus being an attractive scaffold to develop new antiparkinsonian agents. Accordingly, we prepared a small library of piperine derivatives and screened the inhibitory activities towards human MAO isoforms (hMAO-A and hMAO-B). Structure-activity relationship (SAR) studies pointed out that the combination of α-cyano and benzyl ester groups increased both potency and selectivity towards hMAO-B. Kinetic experiments with compounds 7, 10 and 15 indicated a competitive hMAO-B inhibition mechanism. Compounds 15 and 16, at 10 μM, caused a small but significant decrease in P-gp efflux activity in Caco-2 cells. Compound 15 stands out as the most potent piperine-based hMAO-B inhibitor (IC50 = 47.4 nM), displaying favourable drug-like properties and a broad safety window. Compound 15 is thus a suitable candidate for lead optimization and the development of multitarget-directed ligands.