3,4-Dihydro-2H-pyran-2-carbaldehyde

Base Information

• Chemical Name: 3,4-Dihydro-2H-pyran-2-carbaldehyde
• CAS No.: 100-73-2
• Deprecated CAS: 77890-80-3,102265-26-9
• Molecular Formula: C6H8O2
• Molecular Weight: 112.128
• European Community (EC) Number: 202-884-5
• NSC Number: 95413
• UN Number: 2607
• UNII: 49SA3RBS5H
• DSSTox Substance ID: DTXSID30274151
• Nikkaji Number: J21.552J
• Wikidata: Q18018102
• Mol file: 100-73-2.mol

Synonyms:100-73-2;3,4-Dihydro-2H-pyran-2-carbaldehyde;Acrolein dimer;2-Formyl-3,4-dihydro-2H-pyran;Pyran aldehyde;2-Propenal dimer;3,4-Dihydro-2H-pyran-2-carboxaldehyde;2H-PYRAN-2-CARBOXALDEHYDE, 3,4-DIHYDRO-;5-Hexenal, 2,6-epoxy-;NSC 95413;Pyrancarboxaldehyde, dihydro-;2,3-Dihydro-1,4-pyran-2-karboxaldehyd;EINECS 202-884-5;UN2607;BRN 0107244;49SA3RBS5H;2,3-Dihydro-1,4-pyran-2-karboxaldehyd [Czech];NSC-95413;5-17-09-00131 (Beilstein Handbook Reference);2,6-epoxy-5-hexenal;5-Hexenal,6-epoxy-;Acrolein dimer, stabilized;UNII-49SA3RBS5H;WLN: T6O BUTJ FVH;2-Formyl-3,4-dihydropyran;UN 2607 (Salt/Mix);SCHEMBL259004;Pyran aldehyde (Acrolein dimer);DTXSID30274151;3,4-Dihydro-2-formyl-2H-pyran;NSC95413;MFCD00059170;NA2607;AKOS009156968;2H-Pyran-2-carboxaldehyde,4-dihydro-;3,4-dihydro-2H-pyran-2-carboxaldeyde;PB24581;3,4-Dihydro-2-carboxaldehyde-2H-pyran;3,4-Dihydro-2H-pyran-2-carbaldehyde #;AS-33162;LS-127272;FT-0718602;EN300-50137;A934015;J-000206;Q18018102;Acrolein dimer, stabilized [UN2607] [Flammable liquid];Z600389890;Acrolein dimer, stabilized [UN2607] [Flammable liquid]

Chemical Property of 3,4-Dihydro-2H-pyran-2-carbaldehyde

Chemical Property:

• Appearance/Colour: colorless or yellow liquid with a pungent disagreeable odor
• Vapor Pressure: 3.28mmHg at 25°C
• Melting Point: -99.9°C
• Refractive Index: n20/D 1.466(lit.)
• Boiling Point: 185.1 °C at 760 mmHg
• Flash Point: 73.4 °C
• PSA: 26.30000
• Density: 1.151 g/cm³
• LogP: 0.87800
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 107
• Transport DOT Label: Flammable Liquid

Purity/Quality:

96%, ^*data from raw suppliers

3,4-Dihydro-2H-pyran-2-carbaldehyde 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-20/21/22-36/37/38-41
• Safety Statements: 16-26-33-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1CC(OC=C1)C=O
• General Description: 2-Formyl-3,4-dihydro-2H-pyran, also known as acrolein dimer, is a versatile intermediate in organic synthesis. It serves as a key precursor in Lewis acid-catalyzed reactions for constructing benzofurans and tetrahydrobenzofurans, as well as in lipase-mediated enantioselective synthesis of levoglucosenone, a valuable chiral building block. Its reactivity enables applications in pharmaceutical chemistry and the production of optically active compounds.

Technology Process of 3,4-Dihydro-2H-pyran-2-carbaldehyde

There total 8 articles about 3,4-Dihydro-2H-pyran-2-carbaldehyde 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: 91.0%

acrolein (107-02-8,25068-14-8) → acrolein dimer (100-73-2)

Guidance literature:

With Sodium tripolyphosphate; acetaldehyde; hydroquinone; for 0.0833333h; Irradiation;

DOI:10.1002/jccs.199700092

Reference yield:

methyl vinyl ketone (78-94-4,25038-87-3) + acrolein (107-02-8,25068-14-8) → acrolein dimer (100-73-2) + acetyl-2 dihydro-2,3 4H-pyranne (3749-34-6) + 6-methyl-3,4-dihydro-2H-pyran-2-carbaldehyde (64881-26-1) + 2-acetyl-6-methyl-2,3-dihydropyran (28450-02-4)

Guidance literature:

In 1,2-dimethoxyethane; benzene; Temperature; Kinetics; Mechanism;

DOI:10.1002/anie.200903293

Reference yield:

2-hydroxymethyl-3,4-dihydro-2H-pyran (3749-36-8) → acrolein dimer (100-73-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Multistep reaction; -70 deg C;

upstream raw materials:

acrolein

2-hydroxymethyl-3,4-dihydro-2H-pyran

-butyl vinyl ether

acrylic acid methyl ester

Downstream raw materials:

benzoyloxy-(3,4-dihydro-2H-pyran-2-yl)-acetonitrile

opt.-inakt. Phenyl-<3,4-dihydro-2H-pyranyl-(2)>-methanol

3,4-dihydro-2H-pyran-2-carbaldehyde-methallylimine

Tetrahydropyran-2-methanol

Refernces

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds

10.1021/acs.joc.9b00270

The study presents a novel Lewis acid-catalyzed approach for the synthesis of benzofurans and 4,5,6,7-tetrahydrobenzofurans from acrolein dimer and 1,3-dicarbonyl compounds. The method employs N-bromosuccinimide (NBS) as an oxidizing agent and utilizes a combination of Lewis acid catalysts to achieve high yields of 2,3-disubstituted benzofurans. The researchers successfully synthesized two commercial drug molecules, benzbromarone and amiodarone, using this method. The study also explores the substrate scope and optimizes the reaction conditions. Additionally, the authors propose a mechanism involving NBS-assisted auto-tandem catalysis and provide evidence by isolating an intermediate that can be further converted to tetrahydrobenzofurans. This work offers an efficient and practical route to synthesize benzofuran derivatives with potential applications in pharmaceutical chemistry.

Lipase-Mediated Synthesis of Both Enantiomers of Levoglucosenone from Acrolein Dimer

10.1002/1615-4169(200108)343:6/7<618::AID-ADSC618>3.0.CO;2-E

The research focuses on the synthesis of both enantiomers of levoglucosenone from acrolein dimer using lipase-mediated kinetic hydrolysis. The purpose of this study was to develop an efficient method for the synthesis of levoglucosenone, a chiral building block with high chemical potential, which is utilized in the construction of various optically active compounds. The researchers concluded that they had successfully developed a new route to racemic levoglucosenone and its resolution into both enantiomers of enantiopure levoglucosenone. Key chemicals used in the process included acrolein dimer, sodium borohydride, vinyl acetate, p-toluenesulfonic acid, m-chloroperbenzoic acid, o-iodoxybenzoic acid, and various lipases for the enzymatic resolution steps. The synthesis involved several steps, including reduction, oxidative acetalization, Swern oxidation, and dehydrogenation, ultimately leading to the desired enantiomers of levoglucosenone.