Acrolein diethyl acetal

Base Information

• Chemical Name: Acrolein diethyl acetal
• CAS No.: 3054-95-3
• Molecular Formula: C7H14O2
• Molecular Weight: 130.187
• Hs Code.: 29110000
• European Community (EC) Number: 221-276-0
• NSC Number: 60135
• UN Number: 2374
• UNII: 33XN703369
• DSSTox Substance ID: DTXSID0020024
• Nikkaji Number: J83.950G
• Wikidata: Q27256306
• ChEMBL ID: CHEMBL3182978
• Mol file: 3054-95-3.mol

Synonyms:acrolein diethyl acetal;acrolein diethylacetal

Chemical Property of Acrolein diethyl acetal

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 16mmHg at 25°C
• Melting Point: 120-125°C
• Refractive Index: n20/D 1.398(lit.)
• Boiling Point: 123.5 °C at 760 mmHg
• Flash Point: 22.3 °C
• PSA: 18.46000
• Density: 0.854 g/cm³
• LogP: 1.57150
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 130.099379685
• Heavy Atom Count: 9
• Complexity: 65.3
• Transport DOT Label: Flammable Liquid

Purity/Quality:

98%, ^*data from raw suppliers

Acrolein Diethyl Acetal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36
• Safety Statements: 9-16-26-33-29-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Acetals
• Canonical SMILES: CCOC(C=C)OCC
• Uses: Acrolein diethyl acetal is a reagent used for the synthesis of a variety of compounds, including cinnamaldehydes. Acrolein diethyl acetal is widely used to carry out chemoselective Heck arylation to synthesize either 3-arylpropanoate esters or cinnamaldehyde derivatives.It can also be used as one of the precursors to synthesize natural products like (?)-(Z)-Deoxypukalide, (?)-Laulimalide, botryodiplodin, neolaulimalide and isolaulimalide.

Technology Process of Acrolein diethyl acetal

There total 27 articles about Acrolein diethyl acetal 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: 83.0%

aminopropane diethyl acetal (41365-75-7) → acrylaldehyde diethyl acetal (3054-95-3)

Guidance literature:

With 2-hydroxynitrobenzene; strontium chloride; sodium sulfite; In acetonitrile; at 135 ℃; for 9h; Temperature; Time;

Reference yield: 74.0%

orthoformic acid triethyl ester (122-51-0) + acrolein (107-02-8,25068-14-8) → acrylaldehyde diethyl acetal (3054-95-3)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1002/hlca.200800446

Reference yield: 11.0%

phenylmagnesium bromide → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + acrylaldehyde diethyl acetal (3054-95-3) + α-phenylallyl ethyl ether (14093-65-3)

Guidance literature:

1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1246/cl.1985.351

upstream raw materials:

3-chloro-1,1-diethoxy-propane

3-butoxy-propionaldehyde diethylacetal

orthoformic acid triethyl ester

acrolein

Downstream raw materials:

1-ethoxy-1-pentene

3-Triaethylsilyl-propionsaeure-aethylester

ethyl 2-ethoxyethanoate

methyl 2-carbomethoxy-2,5-diethoxy-(E)-4-pentenoate

Refernces

Reductive Lithiation in the Absence of Aromatic Electron Carriers. A Steric Effect Manifested on the Surface of Lithium Metal Leads to a Difference in Relative Reactivity Depending on Whether the Aromatic Electron Carrier Is Present or Absent

10.1021/acs.joc.5b01136

The research focuses on reductive lithiation, a method for preparing organolithium compounds, typically involving the use of aromatic radical-anions or lithium metal in the presence of an aromatic electron transfer catalyst. The study explores the reductive lithiation of alkyl phenyl thioethers, alkyl chlorides, acrolein diethyl acetal, and isochroman using lithium dispersion as a source of lithium metal, absent of an electron transfer agent. The experiments involved various substrates with different alkyl group sizes to investigate the steric effect on the reaction's efficiency and selectivity. The analyses included DFT calculations to understand the bond dissociation energies and adsorption geometries on the lithium surface, as well as traditional organic chemistry techniques such as NMR spectroscopy and mass spectrometry to characterize the products and monitor the progress of the reactions. The results showed that lithium dispersion could achieve reductive lithiation efficiently and that the reactivity order was reversed when comparing the presence or absence of an electron transfer agent, with smaller alkyl groups exhibiting greater reactivity. This discovery challenges the prevailing understanding of reductive lithiation and highlights the significance of steric effects in these reactions.