40516-46-9

Basic information

• Product Name: diethyl (ethoxymethyl)malonate
• Synonyms: diethyl (ethoxymethyl)malonate;(Ethoxymethyl)malonic acid diethyl ester;2-(Ethoxymethyl)malonic acid diethyl ester;Ethoxymethylmalonic acid diethyl ester;Propanedioic acid, (ethoxyMethyl)-, diethyl ester;diethyl 2-(ethoxymethyl)malonate
• CAS NO: 40516-46-9
• Molecular Formula: C₁₀H₁₈O₅
• Molecular Weight: 218.24692
• EINECS: 254-950-8
• Mol File: 40516-46-9.mol

Chemical Properties

• Boiling Point: 278.4°Cat760mmHg
• Flash Point: 116.8°C
• Appearance: /
• Density: 1.052g/cm³
• Vapor Pressure: 0.00428mmHg at 25°C
• Refractive Index: 1.43
• PKA: 11.74±0.59(Predicted)
• CAS DataBase Reference: diethyl (ethoxymethyl)malonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (ethoxymethyl)malonate(40516-46-9)
• EPA Substance Registry System: diethyl (ethoxymethyl)malonate(40516-46-9)

Safety Data

• Hazardous Substances Data: 40516-46-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl (ethoxymethyl)malonate is utilized as a key intermediate in the synthesis of pharmaceuticals for its ability to participate in multiple chemical reactions, facilitating the development of new drug molecules.
Used in Agrochemical Industry:
In the agrochemical sector, diethyl (ethoxymethyl)malonate is employed as a precursor in the production of various agrochemicals, contributing to the creation of effective solutions for agricultural applications.
Used in Organic Synthesis:
Diethyl (ethoxymethyl)malonate is used as a versatile reagent in organic synthesis for its capacity to undergo esterification, alkylation, and condensation, enabling the construction of complex organic molecules for a wide range of applications.
Used in Fine Chemicals Production:
diethyl (ethoxymethyl)malonate is also used as a building block in the production of fine chemicals, where its ability to form more complex molecules is crucial for developing high-quality specialty products.

InChI:InChI=1/C10H18O5/c1-4-13-7-8(9(11)14-5-2)10(12)15-6-3/h8H,4-7H2,1-3H3

Upstream product

• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 105-53-3 diethyl malonate 
• 3188-13-4 ethyl chloromethyl ether 

Downstream Products

• 3377-20-6 diethyl methylenemalonate 
• 75907-56-1 2-[(3-Phenyl-isothiazol-5-ylamino)-methylene]-malonic acid diethyl ester 
• 72798-17-5 2-phenylsulfanylmethylene-malonic acid diethyl ester 
• 139172-28-4 6-ethoxycarbonyl-2-(2,4-dichlorophenyl)-5H-1,3,4-thiadiazolo(3,2-a)pyrimidin-5-one 
• 13388-74-4 ethyl 1H-benzo[g]quinoline-4,5,10-trione-3-carboxylate 
• 321162-53-2 1H-benzo[g]quinoline-4,5,10-trione 
• 680859-85-2 ethyl 10-benzyloxy-5-hydroxybenzo[g]quinolin-4(1H)-one-3-carboxylate 
• 51592-69-9 1,5-Dicarbethoxy-3,3-dimethylcyclohexen 
• 51593-44-3 cis-5,5-Dimethylcyclohexan-1,3-dicarbonsaeurediethylester 
• 51592-66-6 6-Dimethylamino-5.5-dimethyl-cyclohexan-1.1.3.3-tetracarbonsaeure-tetraethylester 
• 802916-50-3 C₁₅H₁₇N₃O₃ 
• 16600-22-9 7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester 
• 19499-19-5 4,7-dichloroquinoline-3-carboxylic acid ethyl ester 
• 206258-97-1 ethyl 4-chloro-8-bromo-3-quinolinecarboxylate 

Relevant articles and documents

Selective reduction of mono- and disubstituted olefins by NaBH4 and catalytic RuCl3

Direct use of the relatively inexpensive reagent, RuCl3 × H2O, as a catalyst for the reductions of olefins in the presence of water is reported. The combination of cheap and readily available sodium borohydride and a catalytic amount of RuCl3 × H2O selectively reduces mono- and disubstituted olefins, whereas trisubstituted olefins, unless activated, and benzyl ethers remain inert.

Synthesis of 2,3-disubstituted indoles by radical cyclization with hypophosphorous acid and its application to total synthesis of (±)-catharanthine

Radical cyclization of o-alkenylthioanilides using hypophosphorous acid and AIBN in the presence of Et3N proceeded smoothly to furnish the corresponding 2,3-disubstituted indoles in high yields. Utilizing the newly developed cyciization condition, a stereocontrolled total synthesis of (±)-catharanthine has been completed.

Structural studies on dioxan-2-ylium ions: intramolecular attack of an oxygen atom on a carbenium ion centre

As models for the ionization of orthoesters, a series of 1,3-dioxan-2-ylium salts have been prepared and characterized.The properties of 1,3-dioxan-2-ylium hexachloroantimonate 1, 5-ethoxymethyl-1,3-dioxan-2-ylium hexachloroantimonate 2, 2-methyl-5-ethoxymethyl-1,3-dioxan-2-ylium hexachloroantimonate 3, and 2-phenyl-5-ethoxymethyl-1,3-dioxan-2-ylium hexachloroantimonate 4, have been studied by 1H and 13C NMR spectroscopy.The structures of 3 and 4 have been determined using X-ray crystallography.Salts 3 and 4 both crystallize in monoclinic crystal systems.For 3, the space group is C2/c, with a=30.192(4) Angstroem, b=9.613(2) Angstroem, c=12.742(2) Angstroem, β=109.71(1) deg, V=3482(1) Angstroem3, and Z=8.Complex 4 crystallizes in the space group P21/n, with a=10.638(2) Angstroem, b=11.849(2) Angstroem, c=16.970(3) Angstroem, β=106.84(1) deg, V=2047(1) Angstroem3, and Z=4.The geometries of 3 and 4 are similar with the ether oxygen disposed over the dioxan-2-ylium ring.However, the interaction between the ether oxygen and the cationic centre is not significant due to the large internuclear distance observed.The cation 5, in which the carbon chain length between the ether oxygen and C(5) was increased, was prepared.This ion was found to undergo a reversible, intramolecular rearrangement resulting in the formation of 1-methyl-4-acetoxymethyl-tetrahydroguranyl oxonium hexachloroantimonate 11.

Method of preparing alkoxymethylenemalonic acid esters

Preparation of alkoxymethylene malonic acid ester of formula: STR1 wherein R and each R' is an alkyl group, by reaction of malonic acid diester and ortho formic acid triester. The reaction is performed in the presence of a carboxylic acid or a carboxylic acid anhydride and a Lewis acid. The ortho ester is initially present in amount of at least 1,4 mols per mole of the malonic acid ester starting material. Alcohol formed during the reaction is removed during the reaction.