Ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate

Base Information

• Chemical Name: Ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate
• CAS No.: 24393-66-6
• Molecular Formula: C12H12 O4
• Molecular Weight: 220.225
• Hs Code.: 2932999099
• European Community (EC) Number: 246-220-2
• NSC Number: 162322
• DSSTox Substance ID: DTXSID201030725
• Nikkaji Number: J287.235H,J672.961D
• Wikidata: Q76305762
• ChEMBL ID: CHEMBL2299422
• Mol file: 24393-66-6.mol

Synonyms:24393-66-6;14731-78-3;Ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate;ethyl 3-(2H-1,3-benzodioxol-5-yl)prop-2-enoate;ethyl (2E)-3-(1,3-benzodioxol-5-yl)acrylate;ethyl (E)-3-(1,3-benzodioxol-5-yl)prop-2-enoate;3-(1,3-Benzodioxol-5-yl)-2-propenoic acid ethyl ester;AI3-02256;EINECS 246-220-2;2-Propenoic acid, 3-(1,3-benzodioxol-5-yl)-, ethyl ester;Ethyl 3-(benzo[d][1,3]dioxol-5-yl)acrylate;(E)-Ethyl 3-(benzo[d][1,3]dioxol-5-yl)acrylate;ETHYL (2E)-3-(2H-1,3-BENZODIOXOL-5-YL)PROP-2-ENOATE;Ethyl piperonylideneacetate;SCHEMBL3565699;CHEMBL2299422;PTMOFMXIIKUMTA-GQCTYLIASA-N;DTXSID201030725;MFCD01696332;NSC162322;AKOS015950754;NSC 162322;NSC-162322;Ethyl 3-(1,3-benzodioxol-5-yl)acrylate;LS-07483;LS-123562;CS-0530776;EN300-70542;Ethyl 3-(1,3-benzodioxol-5-yl)acrylic acid;EN300-364851;ethyl 3-(1,3-dioxaindan-5-yl)prop-2-enoate;(E)-1,3-Benzodioxole-5-acrylic acid ethyl ester;A808636;ethyl (2E)-3-(1,3-dioxaindan-5-yl)prop-2-enoate;Ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate;Z53837255;Ethyl (2E)-3-(1,3-benzodioxol-5-yl)-2-propenoate #;(E)-3-(1,3-benzodioxol-5-yl)-2-propenoic acid ethyl ester

Chemical Property of Ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate

Chemical Property:

• Vapor Pressure: 0.000106mmHg at 25°C
• Melting Point: 51-53 °C
• Boiling Point: 337.2°Cat760mmHg
• Flash Point: 149.2°C
• PSA: 44.76000
• Density: 1.236g/cm³
• LogP: 1.99160
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 220.07355886
• Heavy Atom Count: 16
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

ethyl(2E)-3-(1,3-benzodioxol-5-yl)acrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC2=C(C=C1)OCO2
• Isomeric SMILES: CCOC(=O)/C=C/C1=CC2=C(C=C1)OCO2

Technology Process of Ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate

There total 37 articles about Ethyl (E)-3-(1,3-benzodioxol-5-yl)acrylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

piperonal (120-57-0,30024-74-9) + hydrogen ethyl malonate (1071-46-1) → ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate (24393-66-6)

Guidance literature:

With poly{styrene-co-[4-(N-methyl-N-vinylbenzyl-amino)pyridine]-co-[1-phenyl-3-(4-vinylbenzyl)piperazine]}; In N,N-dimethyl-formamide; at 50 ℃; optical yield given as %de; stereoselective reaction;

DOI:10.1055/s-0030-1260808

Reference yield: 96.0%

piperonol (495-76-1) + (ethoxycarbonylmethyl)triphenylphosphonium chloride (17577-28-5) → ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate (24393-66-6)

Guidance literature:

With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydroxide; copper(ll) bromide; In formamide; acetonitrile; at 65 ℃; for 24h; diastereoselective reaction; Schlenk technique;

DOI:10.1055/s-0036-1590904

Reference yield: 96.0%

piperonal (120-57-0,30024-74-9) + ethyl bromoacetate (105-36-2) → ethyl (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylate (24393-66-6)

Guidance literature:

With N¹,N³,N⁵-tris(4-(diphenylarsino)phenyl)benzene-1,3,5-tricarboxamide; potassium carbonate; In neat (no solvent); at 80 ℃; for 1h; stereoselective reaction;

DOI:10.1080/00397911.2016.1186698

upstream raw materials:

piperonal

hydrogen ethyl malonate

diethoxyphosphoryl-acetic acid ethyl ester

ethanol

Downstream raw materials:

(2S,3S)-2-Benzo[1,3]dioxol-5-yl-5-(3,4-dimethoxy-phenyl)-2,3-dihydro-furan-3,4-dicarboxylic acid diethyl ester

(5-ethoxycarbonyl-4-hydroxy-c-2,t-6-bis(3,4-methylenedioxyphenyl)-t-3-phenylcyclohex-4-ene-r-1,3-carbolactone)

(E)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-ol

Refernces

• 1、 Ramavath, Vijayalakshmi,Rupanawar, Bapurao D.,More, Satish G.,Bansode, Ajay H.,Suryavanshi, Gurunath. "Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents". . p. 8806 - 8813. Retrieved 2021/05/26.
• 2、 Banerjee, Prabal,Kumar, Pankaj,Kumar, Rakesh. "Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine". supporting information. p. 6535 - 6550. Retrieved 2020/06/09.