4619-66-3

Basic information

• Product Name: Methyl diacetoacetate
• Synonyms: Methyl diacetoacetate;methyl 2-acetylacetoacetate;Butanoic acid, 2-acetyl-3-oxo-, methyl ester;2-Acetyl-3-oxobutanoic acid methyl;2-Acetyl-3-oxobutyric acid methyl;Methyl=diacetylacetate;2-acetyl-3-oxo-butyric acid Methyl ester;Methyl 2-acetyl-3-oxobutanoate
• CAS NO: 4619-66-3
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.1519
• EINECS: 225-031-9
• Mol File: 4619-66-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 203.22°C (rough estimate)
• Flash Point: 82.4°C
• Appearance: /
• Density: 1.1229 (rough estimate)
• Vapor Pressure: 0.208mmHg at 25°C
• Refractive Index: 1.4610 (estimate)
• PKA: 6.91±0.46(Predicted)
• CAS DataBase Reference: Methyl diacetoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl diacetoacetate(4619-66-3)
• EPA Substance Registry System: Methyl diacetoacetate(4619-66-3)

Safety Data

• Hazardous Substances Data: 4619-66-3(Hazardous Substances Data)

Usage

General Description

Methyl diacetoacetate is a chemical compound with the molecular formula C7H10O4. It is a colorless liquid with a slightly fruity odor, commonly used as a pharmaceutical intermediate and as a reagent in organic synthesis. Methyl diacetoacetate is known for its versatile reactivity, serving as a building block for the synthesis of various compounds, including pharmaceuticals, agrochemicals, and materials. It is also used in the production of flavoring and fragrance compounds, as well as in the manufacture of certain polymers and resins. Methyl diacetoacetate is considered a valuable chemical for its role in the production of a wide range of useful and important products.

InChI:InChI=1/C7H10O4/c1-4(8)6(5(2)9)7(10)11-3/h6H,1-3H3

Upstream product

• 463-51-4 Ketene 
• 105-45-3 acetoacetic acid methyl ester 
• 124-38-9 carbon dioxide 
• 123-54-6 acetylacetone 
• 74-88-4 methyl iodide 
• 75-36-5 acetyl chloride 
• 67-56-1 methanol 
• 60700-15-4 3-acetyl-(3H,5H)-tetrahydrothiophene-2,4-dione 
• 34284-28-1 sodium methyl acetoacetate 
• 4525-27-3 β-acetoxy-crotonic acid methyl ester 

Downstream Products

• 123-54-6 acetylacetone 
• 1255639-37-2 Methoxycarbonyl-curcumin 
• 1041464-57-6 methyl 3,5-dimethyl-1(4-sulfamoylphenyl)-1H-pyrazole-4-carboxylate 
• 73773-25-8 methyl 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carboxylate 

Relevant articles and documents

Ambient carboxylation on a supported reversible CO2 carrier: Ketone to β-keto ester

A reversible CO2 carrier (RCC) has been developed to perform carboxylation of ketone to β-ketoester under ambient CO2 pressure and temperature. RCC has been synthesized by immobilizing 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) on methylhydrosiloxane support and reacting with CO2 with 100% degree of functionalisation. RCC is found to be recyclable and shows retention of activity in 5 recycles. CO2 absorption under ambient temperature and desorption at 120°C renders the material suitable for carrying out carboxylation reactions at 25°C with excellent yields. The yield of the reaction can reach up to 100% with TON 200 in 4 h. The extent of the reaction primarily depends upon enol content of the substrate. β-Ketoacid produced during the reaction can be isolated and converted to its corresponding methyl ester derivative by reacting with methyl iodide.

Improved synthesis of alkyl diacetylacetates

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Cycloaddition of cross-conjugated trienes to halogenated quinones

The chemoselectivity of [4+2] cycloadditions involving electron-rich cross-conjugated trienes and halogenated quinones has been examined. The approach provides improved preparations of 6-acetyl-2,3,7-trihydroxyjuglone, solorinic and norsolorinic acids, and averythrin. It also confirms the structure proposed for haematommone and 3,8-dihydroxy-4-methoxy-2-methoxycarbonyl-1-methylanthraquinone but invalidates that of sopheranin.