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
• Uses: NSC 95413 is used as a reagent in chemical processes.

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:

(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2E)-3-[(2R)-6-hydroxytetrahydro-2H-pyran-2-yl]acrylate

10-benzyl 1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl] (2E,4R,8E)-4-hydroxydeca-2,8-dienedioate

10-benzyl 1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl] (2E,4R,8E)-4-[(diphenylphosphoryl)oxy]deca-2,8-dienedioate

Jasmin lactone

Refernces

• 1、 Potnis et al.. "-". . p. 78,80. Retrieved 1963.
• 2、 Karpyak,Makitra,Polyuzhin,Marshalok,Koval'Skii. "Substituents influences on the rate of α-alkylacroleins dimerization". . p. 2373 - 2376. Retrieved 2009.
• 3、 Huang, Wenbo,Xu, Jing,Liu, Changhui,Chen, Zhiyan,Gu, Yanlong. "Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds". . p. 2941 - 2950. Retrieved 2019/02/26.
• 4、 Mohideen, Mazlin,Zulkepli, Suraya,Nik-Salleh, Nik-Salmah,Zulkefeli, Mohd,Weber, Jean-Frédéric Faizal Abdullah,Rahman, A. F. M. Motiur. "Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs". . p. 812 - 831. Retrieved 2013/07/26.