(E)-4-(1,3-Benzodioxol-4-yl)-3-butenoic acid

Base Information

• Chemical Name: (E)-4-(1,3-Benzodioxol-4-yl)-3-butenoic acid
• CAS No.: 184360-97-2
• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.198
• DSSTox Substance ID: DTXSID801250692
• Nikkaji Number: J772.894H
• Mol file: 184360-97-2.mol

Synonyms:DTXSID801250692;(E)-4-(1,3-Benzodioxol-4-yl)-3-butenoic acid;(3E)-4-(1,3-Benzodioxol-4-yl)-3-butenoic acid

Chemical Property of (E)-4-(1,3-Benzodioxol-4-yl)-3-butenoic acid

Chemical Property:

• Vapor Pressure: 0.0103mmHg at 25°C
• Melting Point: 34-36 °C (lit.)
• Refractive Index: 1.614
• Boiling Point: 263.4 °C at 760 mmHg
• Flash Point: 103.7 °C
• PSA: 35.53000
• Density: 1.337 g/cm³
• LogP: 1.22780
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 206.05790880
• Heavy Atom Count: 15
• Complexity: 261

Purity/Quality:

98%min ^*data from raw suppliers

3-BUTENOIC ACID, 4-(1,3-BENZODIOXOL-4-YL)-, (3E)- 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=CC=CC(=C2O1)C=CCC(=O)O
• Isomeric SMILES: C1OC2=CC=CC(=C2O1)/C=C/CC(=O)O

Technology Process of (E)-4-(1,3-Benzodioxol-4-yl)-3-butenoic acid

There total 3 articles about (E)-4-(1,3-Benzodioxol-4-yl)-3-butenoic acid 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: 55.0%

4-bromo-benzo[1,3]dioxole (6698-13-1) + (C4H9)3SnCO2CH2CHCHSn(C4H9)3 → (E)-4-((2',3'-methylenedioxy)phenyl)but-3-enoic acid (184360-97-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 100 ℃; for 12h;

DOI:10.1016/S0040-4020(03)00616-1

Reference yield:

C23H36O4Sn → (E)-4-((2',3'-methylenedioxy)phenyl)but-3-enoic acid (184360-97-2) + (Z)-4-[(2,3-methylenedioxy)phenyl]but-3-enoic acid

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 0.25h;

DOI:10.1081/SCC-200032474

Reference yield:

4-bromo-benzo[1,3]dioxole (6698-13-1) + tributylstannyl 4-(tributylstannyl)but-3-enoate → (E)-4-((2',3'-methylenedioxy)phenyl)but-3-enoic acid (184360-97-2)

Guidance literature:

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Yield given. Multistep reaction; 1.) toluene, 100 degC, 12 h; 2.) water, rt, 15 min;

DOI:10.1016/0040-4039(96)01725-X

upstream raw materials:

4-bromo-benzo[1,3]dioxole

Downstream raw materials:

5,6-methylenedioxy-3,4-dihydro-1(2H)-naphthalenone

Refernces

• 1、 Thibonnet, Jér?me,Abarbri, Mohamed,Parrain, Jean-Luc,Duchêne, Alain. "Stereoselective access to functionalized β-γ unsaturated acids". . p. 4433 - 4441. Retrieved 2007/10/03.