5468-23-5

Basic information

• Product Name: DIETHYL ACETOXYMALONATE
• Synonyms: DIETHYL ACETOXYMALONATE;ACETOXYMALONIC ACID DIETHYL ESTER;2-(Acetyloxy)propanedioic acid diethyl ester;Acetyloxymalonic acid diethyl ester;2-acetoxymalonic acid diethyl ester;diethyl 2-acetyloxypropanedioate;Diethyl (acetyloxy)malonate
• CAS NO: 5468-23-5
• Molecular Formula: C₉H₁₄O₆
• Molecular Weight: 218.2
• EINECS: 226-786-7
• Mol File: 5468-23-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 272.4°Cat760mmHg
• Flash Point: 114.7°C
• Appearance: /
• Density: 1.13 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00609mmHg at 25°C
• Refractive Index: 1.434
• CAS DataBase Reference: DIETHYL ACETOXYMALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL ACETOXYMALONATE(5468-23-5)
• EPA Substance Registry System: DIETHYL ACETOXYMALONATE(5468-23-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5468-23-5(Hazardous Substances Data)

Usage

General Description

Diethyl acetoxy malonate is a chemical compound with the molecular formula C10H16O5 and a molecular weight of 216.23 g/mol. It is a derivative of malonic acid and is used in organic synthesis as a reagent for the creation of carboxylic ester and ketone compounds. Diethyl acetoxy malonate is commonly used in the preparation of polyfunctionalized compounds and in the synthesis of various pharmaceuticals and agrochemicals. It serves as a versatile intermediate in the production of many organic compounds and is an important building block in the field of organic chemistry.

InChI:InChI=1/C9H14O6/c1-4-13-8(11)7(15-6(3)10)9(12)14-5-2/h7H,4-5H2,1-3H3

Upstream product

• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 105-53-3 diethyl malonate 
• 64-17-5 ethanol 
• 127-08-2 potassium acetate 
• 685-87-0 Diethyl 2-bromomalonate 
• 70603-86-0 1-Thiochromanio-bis-(aethoxycarbonyl)-methanid 
• 2216-69-5 1-Methoxynaphthalene 
• 5256-74-6 1,3-diethyl 2-diazopropanedioate 

Downstream Products

• 609-09-6 Diethyl ketomalonate 

Relevant articles and documents

Rh2(esp)2: An Efficient Catalyst for O-H Insertion Reactions of Carboxylic Acids into Acceptor/Acceptor Diazo Compounds

Rh2(esp)2 has been identified as a highly efficient catalyst for O-H insertion of carboxylic acids into acceptor/acceptor diazo compounds. The insertion reaction proceeds in CH2Cl2 within minutes at room temperature in excellent yields and accommodates carboxylic acids having varying functionalities including amino acids, free alcoholic and phenolic O-H, indole N-H, alkenes, alkynes, and substituted aromatics. In addition, the reaction tolerates a broad range of stable diazo compounds carrying diverse functional groups. Diazo-Acid Insertion: A novel Rh2(esp)2-catalyzed O-H insertion reaction of carboxylic acids into acceptor/acceptor diazo compounds has been developed. The reaction is highly chemoselective and accommodates carboxylic acids having varying functionalities including amino acids, free alcoholic and phenolic O-H, indole N-H, alkenes, alkynes, and substituted aromatics.

Oxidation of Malonic Acid Derivatives by Manganese(III) Acetate. Aromatic Malonylation Reaction. Scope and Limitations

The oxidation of malonic acid derivatives RCH(COOR1)COOR2 (R1 = or R2 = H, Me, Et; R = H, Me, Et, n-Bu, i-Pr, C6H5, 4-OMeC6H4) by anhydrous or dihydrated manganese(III) acetate was studied in acetic acid in the presence of aromatic substrates at 20-80 deg C, generally with stoichiometric amounts of reagents.Electron-rich aromatics (IP 7.5 eV) underwent nuclear acetoxylation or quinone formation, the process being exclusive with anthracene and competitive with nuclear malonylation for 1- and 2-methoxynaphthalene.With other less electron-rich substrates (IP 8.5 eV) only the products coming from the oxidation of the malonic acid derivatives (aryl malonates, tartronates, etc., or dimerization and disproportionation products) were observed.The selectivity and the yield of aromatic substitution by the malonyl group was found to be affected by the electron density of the aromatic ring, the steric inhibition of substituents in the Mn(III) oxidation of the malonic acid derivative, the oxidizability of malonyl radical by Mn(III), the base (acetate ions or water) eventually present in the medium, and the further easy oxidation of the primary aryl malonate product, when unsubstituted dialkylmalonates or malonic acid were used.A mechanism is suggested in which inner-sphere electron transfer from Mn(III)-malonate complex affords Mn(II) malonyl radicals that are partitioned between oxidation, dimerization (or disproportionation), and reversible addition to the aromatics.

THE DEGRADATION OF CARBOXYLIC ACIDS INTO ALDEHYDES. REGIOSELECTIVE α-ACETOXYLATION OF 1,2,4-TRIAZOLIUM SALTS WITH DIACETOXYIODATE(1)ANION

A novel method was developed for degradation of carboxylic acid into aldehydes containing one C atom less whose key step consists in α-acetoxylation of 5-alkyl-3-methylthio-1,4-diphenyl-1,2,4-triazolium iodides by (diacetoxyiodo)benzene.The mechanism of the regioselective α-acetoxylation was studied and the diacetoxy-iodate(1)anion was shown to be the actual oxidising agent.Further oxidation reactions of tetraethylammonium diacetoxyiodate(1) were investigated.A novel method was developed for the oxidation of primary alkyl amines into aldehydes by the novel heterocyclic reagent 5-bromo-3-methylthio-1,4-diphenyl-1,2,4-triazolium bromide and diethyl azodicarboxylate.