4,6-Dimethyl-2H-pyran-2-one

Base Information

• Chemical Name: 4,6-Dimethyl-2H-pyran-2-one
• CAS No.: 675-09-2
• Molecular Formula: C7H8 O2
• Molecular Weight: 124.139
• Hs Code.: 2932999099
• European Community (EC) Number: 211-618-7
• NSC Number: 402790
• UNII: G2MA4KIQ1B
• DSSTox Substance ID: DTXSID6060973
• Nikkaji Number: J51.181A
• Wikidata: Q72471933
• Metabolomics Workbench ID: 133050
• ChEMBL ID: CHEMBL372284
• Mol file: 675-09-2.mol

Synonyms:4,6-Dimethyl-2H-pyran-2-one;4,6-Dimethyl-2-pyrone;675-09-2;Mesitene lactone;4,6-dimethylpyran-2-one;2H-PYRAN-2-ONE, 4,6-DIMETHYL-;4,6-Dimethylcoumalin;4,6-Dimethyl-alpha-pyrone;2,4-Dimethyl-alpha-pyrone;4,6-Dimethyl-pyran-2-one;2,4-Dimethyl-.alpha.-pyrone;4,6-Dimethyl-.alpha.-pyrone;EINECS 211-618-7;G2MA4KIQ1B;NSC 402790;BRN 0002468;CHEMBL372284;Sorbic acid, 5-hydroxy-3-methyl-, .delta.-lactone;NSC-402790;5-17-09-00409 (Beilstein Handbook Reference);MFCD00075555;NSC402790;UNII-G2MA4KIQ1B;4,6-dimethyl-2-pyranone;SCHEMBL981128;WLN: T6OVJ D1 F1;4,6-Dimethyl- alpha -pyrone;2H-Pyran-2-one,6-dimethyl-;DTXSID6060973;4,6-Dimethyl-alpha-pyrone, 98%;BDBM50167999;AKOS015967436;LS-127441;FT-0617265;4,6 - dimethyl - 2H - pyran - 2 - one;A835775

Chemical Property of 4,6-Dimethyl-2H-pyran-2-one

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 0.0294mmHg at 25°C
• Melting Point: 48-50 ºC
• Refractive Index: 1.3810 (estimate)
• Boiling Point: 245 ºC
• Flash Point: 90.1 ºC
• PSA: 30.21000
• Density: 1.065 g/cm³
• LogP: 1.25660
• Water Solubility.: 242.4g/L(59.7 oC)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 124.052429494
• Heavy Atom Count: 9
• Complexity: 199

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,6-Dimethyl-α-pyrone 98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC(=C1)C
• Uses: 4,6-Dimethyl-α-pyrone (Me21) has been used in the preparation of G4C{Me21} via reacting with tetra-p-sulfocalix[4]arene (C) and guanidine hydrochloride (GCl). It may be used in the preparation of host-guest complex G4C{Me21} by reacting with crystalline guanidinium-sulfonate-calixarene (G4C). This complex on UV irradiation afforded 1,3-dimethylcyclobutadiene (Me2CBD).

Technology Process of 4,6-Dimethyl-2H-pyran-2-one

There total 28 articles about 4,6-Dimethyl-2H-pyran-2-one 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: 85.0%

(Z)-3-iodobut-2-enoic acid (34450-60-7) + allenyltributylstannane (53915-69-8) → 4,6-Dimethyl-2-pyron (675-09-2)

Guidance literature:

(Z)-3-iodobut-2-enoic acid; With tetrabutylammomium bromide; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

allenyltributylstannane; In N,N-dimethyl-formamide; for 4h;

DOI:10.1021/jo050638z

Reference yield: 79.0%

methylmagnesium chloride (676-58-4) + 6-methyl-2-pyrone-4-trifluoromethanesulfonate (488788-59-6) → 3,5-dimethyl-2,4-hexadienoic acid (83612-61-7,83612-62-8,87252-17-3) + 4,6-Dimethyl-2-pyron (675-09-2)

Guidance literature:

With iron(III)-acetylacetonate; In tetrahydrofuran; diethyl ether; at -78 ℃; Inert atmosphere;

DOI:10.1002/anie.201307028

Reference yield: 78.0%

4-acetoxy-6-methyl-2H-2-pyranone (22073-80-9) + methylmagnesium bromide (75-16-1) → 4,6-Dimethyl-2-pyron (675-09-2)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; iron(II) chloride; In tetrahydrofuran; at 0 ℃; for 1h; Schlenk technique; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201504524

upstream raw materials:

isodehydracetic acid

(4-methyl-6-oxo-6H-pyran-2-yl)-acetic acid

3-acetyl-4-methyl-2H-pyran-2,6(3H)-dione

acetic acid tert-butyl ester

Downstream raw materials:

6-Hydroxy-2,4-lutidin

4,6-dimethyl-2-phenyl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one

3,5-dimethyl-2,4-hexadienoic acid

3-bromo-4,6-dimethyl-2H-pyran-2-one

Refernces

• 1、 Legrand, Yves-Marie,Gilles, Arnaud,Petit, Eddy,Van Der Lee, Arie,Barboiu, Mihail. "Unprecedented synthesis of 1,3-dimethylcyclobutadiene in the solid state and aqueous solution". . p. 10021 - 10028. Retrieved 2011.
• 2、 G?rtner, Dominik,Stein, André Luiz,Grupe, Sabine,Arp, Johannes,Von Wangelin, Axel Jacobi. "Iron-Catalyzed Cross-Coupling of Alkenyl Acetates". . p. 10545 - 10549. Retrieved 2015/09/02.
• 3、 Sun, Chang-Liang,Fuerstner, Alois. "Formal ring-opening/cross-coupling reactions of 2-pyrones: Iron-catalyzed entry into stereodefined dienyl carboxylates". supporting information. p. 13071 - 13075. Retrieved 2014/01/06.