3385-34-0

Basic information

• Product Name: 5-Carbethoxy-4,6-dimethyl-2-pyrone
• Synonyms: isodehydroacetic acid ethyl ester;2H-Pyran-5-carboxylic acid, 4,6-dimethyl-2-oxo-, ethyl ester;Ethyl isodehydroacetate,95%;Ethyl isodehydracetate,97%;Ethyl isodehydracetate 99%;Ethyl 4,6-dimethyl-2-pyrone-5-carboxylate;Ethyl 4,6-dimethyl-5-coumalate;ETHYL ISODEHYDRACETATE
• CAS NO: 3385-34-0
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.2
• EINECS: 222-195-3
• Product Categories: Acetics acid and esters
• Mol File: 3385-34-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 17-18 °C(lit.)
• Boiling Point: 290-295 °C(lit.)
• Flash Point: >230 °F
• Appearance: Colorless or pale yellow liquid
• Density: 1.167 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00153mmHg at 25°C
• Refractive Index: n20/D 1.515(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• Water Solubility: Insoluble
• BRN: 145951
• CAS DataBase Reference: 5-Carbethoxy-4,6-dimethyl-2-pyrone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Carbethoxy-4,6-dimethyl-2-pyrone(3385-34-0)
• EPA Substance Registry System: 5-Carbethoxy-4,6-dimethyl-2-pyrone(3385-34-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 3385-34-0(Hazardous Substances Data)

Usage

Description

5-Carbethoxy-4,6-dimethyl-2-pyrone is a chemical compound that belongs to the class of pyrones. It is characterized by the presence of a carbonyl group and two methyl groups at the 4 and 6 positions, as well as a carbethoxy group at the 5 position. 5-Carbethoxy-4,6-dimethyl-2-pyrone has potential applications in various fields due to its unique chemical properties.

Uses

Used in Organic Synthesis:
5-Carbethoxy-4,6-dimethyl-2-pyrone is used as an intermediate in organic synthesis for the preparation of various compounds. Its unique structure allows it to be a versatile building block for the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
5-Carbethoxy-4,6-dimethyl-2-pyrone is used as a raw material in the pharmaceutical industry for the development of new drugs. Its chemical properties make it a promising candidate for the synthesis of novel therapeutic agents.
Used in Agrochemicals:
5-Carbethoxy-4,6-dimethyl-2-pyrone is used in the preparation of insect growth regulators with juvenile hormone activity. This application is particularly useful in the development of environmentally friendly pest control solutions.
Used in Bidentate Ligand Synthesis:
5-Carbethoxy-4,6-dimethyl-2-pyrone is used in the synthesis of bidentate ligands, which are important in coordination chemistry and catalysis. These ligands can be used to create new catalysts for various chemical reactions.

InChI:InChI=1/C10H12O4/c1-4-13-10(12)9-6(2)5-8(11)14-7(9)3/h5H,4H2,1-3H3

Upstream product

• 141-97-9 ethyl acetoacetate 
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• 75-03-6 ethyl iodide 
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• 14369-81-4 ethyl 2,3-butadienoate 
• 7732-18-5 water 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 6127-92-0 E-Ethyl β-chlorocrotonate 
• 71-43-2 benzene 

Downstream Products

• 89193-18-0 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester 
• 7470-42-0 3-acetyl-6-hydroxy-4-methyl-2H-pyran-2-one 
• 32013-63-1 2-acetylemodin 
• 18713-45-6 1,8-diacetoxy-3-methyl-anthraquinone 
• 518-80-9 helminthosporin 
• 481-74-3 Chrysophanol 
• 67116-19-2 3-methyl-pentenedioic acid anhydride 
• 139542-31-7 6-(1'-hydroxy-2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)-4-methylpyran-2-one 
• 139542-29-3 4-methyl-6-(4',6',6'-trimethyl-2'-oxocyclohex-3'-enyl)pyran-2-one 
• 139542-30-6 4-methyl-6-(2',6',6'-trimethyl-4'-oxocyclohex-2'-enyl)pyran-2-one 
• 20110-02-5 (2Z,4E)-5-(1,4-Dihydroxy-2,6,6-trimethyl-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoic acid 
• 21293-29-8 (2Z,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienoic acid 
• 1204-38-2 4,7-dimethylpyrano<4,3-b>pyran-2,5-dione 
• 41264-06-6 methyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate 

Relevant articles and documents

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Catalytic asymmetric tamura cycloadditions

In the presence of a novel, tert-butyl-substituted squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products of significant synthetic interest with excellent enantio- and diastereocontrol. The methodology is of wide scope and encompasses both homophthalic and glutaconic anhydride derivatives, which lead to structurally diverse products. Glutaconic acid-derived anhydrides undergo a clean post-cyclization decarboxylation process which is not a feature of reactions involving homophthalic acid-derived anhydrides. The unusual influence of reaction temperature on diastereocontrol has been probed, with reactions occurring at 30 °C and -30 °C delivering products epimeric at one stereocenter only, in near optical purity. Squared away: The first strategy for bringing about enantioselective Tamura reactions is reported. In the presence of a squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products with excellent enantio- and diastereocontrol. The methodology is of wide scope and leads to structurally diverse products.

MECANISMO DE LA REACCION DE COMPUESTOS 1,3-DICARBONILICOS CON ANHIDRIDO TRIFLICO. CICLACION ANOMALA DEL ESTER ACETILACETICO A 3-ETOXICARBONIL-2,6-DIMETIL-4-PIRONA.

The reaction of ethyl acetoacetate (1) with triflic anhydride (Tf2O) in excess, in the presence of nitriles (3) affords 3-ethoxycarbonyl-2,6-dimethyl-4-pyrone (10), instead of 5-ethoxycarbonyl-4,6-dimethyl-2-pyrone (5), which is the usual product formed in the cyclization of 1 catalyzed by protic or Lewis acids.Palabras clave: 2-pirona, 4-pirona, anhidrido triflico, ester acetylacetico.