1004-36-0

Basic information

• Product Name: 2,6-Dimethyl-4H-pyran-4-one
• Synonyms: 2,6-DIMETHYL-4H-PYRAN-4-ONE;2,6-DIMETHYL-4-PYRONE;2,6-DIMETHYL-GAMMA-PYRONE;2,6-DIMETHYL-G-PYRONE;AURORA KA-6632;2,6-dimethyl-4h-pyran-4-on;2,6-Dimethyl-4-pyranone;2,6-Dimethyl-pyran-4-one
• CAS NO: 1004-36-0
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.14
• EINECS: 213-719-1
• Product Categories: Electronic Chemicals;Ring Systems
• Mol File: 1004-36-0.mol

Chemical Properties

• Melting Point: 133-137 °C(lit.)
• Boiling Point: 248-250 °C(lit.)
• Flash Point: 248-250°C
• Appearance: White to beige/Crystalline Powder or Crystals
• Density: 0.9953
• Vapor Pressure: 0.0235mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Store below +30°C.
• Water Solubility: Slightly soluble in water.
• BRN: 107418
• CAS DataBase Reference: 2,6-Dimethyl-4H-pyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dimethyl-4H-pyran-4-one(1004-36-0)
• EPA Substance Registry System: 2,6-Dimethyl-4H-pyran-4-one(1004-36-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37
• WGK Germany: 3
• RTECS: UQ0780000
• Hazardous Substances Data: 1004-36-0(Hazardous Substances Data)

Usage

Chemical Properties

2,6-Dimethyl-4H-pyran-4-one is white to beige crystalline powder or crystals

Uses

Different sources of media describe the Uses of 1004-36-0 differently. You can refer to the following data:
1. 2,6-Dimethyl-4H-pyran-4-one is used as a fragrance ingredient.
2. 2,6-Dimethyl-4-pyrone is used as a chemical and organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 300, 1951 DOI: 10.1021/ja01145a098

InChI:InChI=1/C7H8O2/c1-5-3-7(8)4-6(2)9-5/h3-4H,1-2H3

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 123-54-6 acetylacetone 
• 3265-58-5 2,6-dimethyl-4-oxopyran-3-carboxylic acid 
• 34793-66-3 hepta-2,5-diyn-4-one 
• 5456-14-4 3,5-diethoxy-carbonyl-2,6-dimethyl-4H-pyran-4-one 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 520-45-6 Dehydracetic acid 
• 626-53-9 1,3-diacetyl acetone 
• 6814-64-8 methylenedimethyl sulfurane 
• 457-23-8 2,6-Dimethyl-4-ethoxypyrylium tetrafluoroborate 
• 93304-66-6 isopropenyl acetoacetate 
• 28884-53-9 hepta-1,5-diyn-4-ol 
• 74628-12-9 (2Z,5E)-2-Hydroxy-6-methoxy-hepta-2,5-dien-4-one 

Downstream Products

• 100915-10-4 2-(2,6-dimethyl-4-oxo-4H-pyran-3-carbonyl)-benzoic acid 
• 773-01-3 2,4,6-trimethylpyrylium tetrafluoroborate 
• 102592-02-9 2,6-dimethyl-3,5-di-p-toluoyl-pyran-4-one 
• 100537-86-8 3-(3,5-dinitro-benzoyl)-2,6-dimethyl-pyran-4-one 
• 28286-88-6 4-dicyanomethylene-2,6-dimethyl-4H-pyran 
• 19396-77-1 3,5-Diacetyl-2,6-dimethyl-4H-pyran-4-one 
• 14258-47-0 2-(2-chloro-styryl)-6-methyl-pyran-4-one 
• 106473-39-6 3-(α-hydroxy-3-nitro-benzyl)-2,6-dimethyl-pyran-4-one 
• 14006-22-5 2-[(E)-2-(3-nitrophenyl)ethenyl]-6-methyl-4H-pyran-4-one 
• 17173-83-0 2,6-di-styryl-pyran-4-one 
• 57961-14-5 2,6-bis-(4-methoxy-styryl)-pyran-4-one 
• 100886-68-8 3-(2,α-dihydroxy-benzyl)-2,6-dimethyl-pyran-4-one 
• 13838-60-3 3-benzoyl-2,6-dimethyl-4-pyrone 
• 72562-99-3 3,5-Dibenzoyl-2,6-dimethyl-4-pyrone 

Relevant articles and documents

Two Unusual Trimers of Diketene

Formation of two unknown, tricyclic trimers of diketene, 3 and 4, was observed in diketene solutions containing (CH3)3SiCl/NaI or TsOH.

Synthesis and Enantioselective Baeyer-Villiger Oxidation of Prochiral Perhydro-pyranones with Recombinant E. coli Producing Cyclohexanone Monooxygenase

Recombinant whole cells of Escherichia coli overexpressing Adnetobacter sp. NCIMB 9871 cyclohexanone monooxygenase (E.C. 1.14.13.22) have been utilized for the Baeyer-Villiger oxidation of prochiral perhydro-pyranones. The spatial limitations of the enzym

Diastereoselective synthesis of cis-2,6-disubstituted perhydro-4-pyranones using elevated pressure hydrogenation

A diastereoselective strategy for the synthesis of γ-pyrons was developed, starting from the Mg diacetonedicarboxylate complex. Initial cyclization with suitable anhydrides or acid chlorides, followed by hydrolytic decarboxylation leads to 2,6-disubstitut

Unusual aluminum chloride-assisted conversion of isopropenyl acetate into 3-acetyl- and 3,5-diacetyl-2,6-dimethyl-4H-pyran-4-ones

Reflux of isopropenyl acetate with an excess of AlCl3 in 1,2-dichloroethane affords 3,5-diacetyl-2,6-dimethyl-4H-pyran-4-one in 17% yield. The mild acidic cleavage of the latter (2% HCl, 20°C, 16 h) gives 3-acetyl-2,6-dimethyl-4H-pyran-4-one in 87% yield, whereas this reaction under more drastic conditions (17% HCl, reflux, 3 h) gives 2,6-dimethyl-4H-pyran-4-one in 61% yield.

HAPPY Dyes as Light Amplification Media in Thin Films

A series of 1H amorphous tri-phenyl pyridine (HAPPY) dyes have been synthesized from luminescent triphenyl-group-containing 2-methyl-6-styryl-substituted-4H-pyran-4-ylidene derivatives in reactions with benzylamine and investigated for suitability as solution-processable light-emitting medium components in thin films for amplified spontaneous emission (ASE). Conversion of a 4H-pyrane ring into a 1H-pyridine fragment enables aggregation-induced emission enhancement (AIEE) behavior in the target products and slightly increases thermal stability, glass transition temperatures, and ASE efficiency with PLQY up to 15% and ASE thresholds as low as 46 μJ/cm2 in neat spin-cast films, although thermal and photophysical properties are mostly dominated by the incorporated electron acceptors. Continued lasing parameter efficiency parameter improvement experiments revealed that no further optimization of HAPPY dyes by doping in polymer matrixes is required as the amplified spontaneous emission thresholds were lowest in pure neat films due to the AIEE phenomenon.

A convenient synthesis of di- and trisubstituted γ-pyrones

Treatment of ketodiynes or allenynones with hot aqueous acid results in the facile formation of di- or tri-substituted γ-pyrrones. The mechanism of this new process was established.

The Generation of a Library of Bromodomain-Containing Protein Modulators Expedited by Continuous Flow Synthesis

A continuous flow process delivering key building blocks for a series of BCP modulator libraries is reported. A dynamically mixed flow reactor emerged as a pivotal technology in both synthesis and isolation phases enabling the processing of slurries and suspensions while maintaining high productivity and reliability. Accordingly, the synthesis of common intermediates in flow were employed to further build a pyridazone-based library (36 compounds) aimed at improving lead compound potency and selectivity while further enabling structure-activity relationship studies of a new BCP modulator family.

Interaction of acetonitrile with trifluoromethanesulfonic acid: Unexpected formation of a wide variety of structures

Interaction of acetonitrile with trifluoromethanesulfonic acid has been studied by multinuclear NMR and ESI-MS. It has been found that the interaction results in formation of a great variety of different cations and neutral compounds which is controlled by the ratio of CH3CN to TfOH. In the presence of an excess of the acid (molar ratio 1:8-14) diprotonated N-acetylacetamidine 1 is formed as the major product, which eventually transforms into protonated acetamidine 3 and acetic acid 4. At molar ratio of (1:1-2) diprotonated 2,4-dimethyl-6-methylidene-3H-1,3,5-triazine 12, tautomer of the diprotonated trimethyl-s-triazine 11, becomes the main product at an early stage of the reaction and diprotonated 1-(dimethyl-1,3,5-triazin-2-yl) prop-1-en-2-ol 15 at a later stage. In the case of a large excess of acetonitrile (4-20:1) trication 17 is formed as a result of the interaction between 11 and 12 along with some oligomers [(CH3CN) 3]n (n = 4-12). The Royal Society of Chemistry 2012.

New pyran dyes for dye-sensitized solar cells

Although ruthenium-based dyes have been extensively used in dye-sensitized solar cells (DSSCs) as photosensitizers, they have several shortcomings such as high costs and potential environmental toxicities. This has stimulated the development of highly efficient organic dyes as photosensitizers. We report the synthesis and photophysical, electrochemical and theoretical properties of novel pyran-based organic dyes (D1, D2, and D3) as well as their applications in DSSCs for the first time. The designed dyes possess a cyanoacrylic acid group as an acceptor and arylamine group as a donor group in a D-π-A configuration. The introduction of varying donor groups resulted in correspondingly different photophysical and electrochemical properties. The DSSCs fabricated using dye D1 showed the highest photovoltaic performance: a maximum incident photon-to-current conversion efficiency (IPCE) of 42%, a short-circuit current density (Jsc) of 4.76 mA cm-2, an open circuit voltage (Voc) of 0.68 V, and a fill factor (FF) of 0.67, corresponding to an overall conversion efficiency of 2.17% under 100 mW cm-2 irradiation. The synthesized dyes with a pyran chromophore and arylamine donor groups showed potentials for applications in DSSCs.

Introduction of adjacent oxygen-functionalities in dimethyl heptalenedicarboxylates

The bromination of dimethyl 8-methoxy-1,6,10-trimethylheptalene-4,5- dicarboxylate (6; Scheme 2) with N-bromosuccinimide (NBS) in N,N-dimethylformamide (DMF) leads in acceptable yields to the corresponding 9-bromoheptalenedicarboxylate 10 (Table 1). Ether