632-56-4

Basic information

• Product Name: TETRAETHYL 1,1,2,2-ETHANETETRACARBOXYLATE
• Synonyms: ETHYL ETHANETETRACARBOXYLATE;1,1,2,2-Ethanetetracarboxylic acid, tetraethyl ester;1,1,2,2-Tetracarbethoxyethane;ethane-1,1,2,2-tetracarboxylicacidtetraethylester;Tetrakis(ethoxycarbonyl)ethane;TETRAETHYL 1,1,2,2-ETHANETETRACARBOXYLATE;tetraethyl ethane-1,1,2,2-tetracarboxylate;Tetraethyl-1,1,2,2-ethanetetracarboxylate 97%
• CAS NO: 632-56-4
• Molecular Formula: C₁₄H₂₂O₈
• Molecular Weight: 318.32
• EINECS: 211-180-7
• Product Categories: C12 to C63;Carbonyl Compounds;Esters;Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 632-56-4.mol
• Article Data: 27

Chemical Properties

• Melting Point: 73-75 °C(lit.)
• Boiling Point: 377.49°C (rough estimate)
• Flash Point: 162.552°C
• Appearance: /
• Density: 1.0640
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4105 (estimate)
• PKA: 10.58±0.59(Predicted)
• BRN: 1805842
• CAS DataBase Reference: TETRAETHYL 1,1,2,2-ETHANETETRACARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAETHYL 1,1,2,2-ETHANETETRACARBOXYLATE(632-56-4)
• EPA Substance Registry System: TETRAETHYL 1,1,2,2-ETHANETETRACARBOXYLATE(632-56-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 632-56-4(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE NEEDLES

Uses

Tetraethyl 1,1,2,2-ethanetetracarboxylate was used in the synthesis of double-ring molecules. It was also used in the preparation of tapt and tapt·4HCl·EtOH·0.5H2O.

Purification Methods

Recrystallise the ester twice from EtOH by cooling to 0o. [Mochizuki et al. Bull Chem Soc Jpn 64 1750 1991, Weinges et al. Angew Chem 93 1008 1981, Beilstein 2 IV 2415.]

InChI:InChI=1/C14H22O8/c1-5-19-10(15)9-14(11(16)20-6-2,12(17)21-7-3)13(18)22-8-4/h5-9H2,1-4H3

Upstream product

• 14064-10-9 diethyl 2-chloromalonate 
• 996-82-7 sodium diethylmalonate 
• 60-29-7 diethyl ether 
• 2303-76-6 sodium diethyl phosphite 
• 854747-47-0 bromo-methanetricarboxylic acid triethyl ester 
• 996-82-7 sodium diethylmalonate 
• 5464-22-2 tetramethyl ethane-1,1,2,2-tetracarboxylate 
• 141-52-6 sodium ethanolate 
• 6174-95-4 1,1,2,2-tetracarboethoxy-ethylene 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 64-17-5 ethanol 
• 685-87-0 Diethyl 2-bromomalonate 
• 100-63-0 phenylhydrazine 
• 5256-74-6 1,3-diethyl 2-diazopropanedioate 

Downstream Products

• 6174-95-4 1,1,2,2-tetracarboethoxy-ethylene 
• 113563-35-2 tetraethyl ester of 1-ethoxyethane-1,1,2,2-tetracarboxylic acid 
• 87497-77-6 2,5-dibenzyl-3a,6a-diethoxycarbonyl-1,4-dioxo-octahydropyrrolo<3,4-c>pyrrole 
• 1372139-11-1 C₃₂H₃₄O₉ 
• 1372138-95-8 C₃₂H₃₄O₈ 
• 5464-22-2 tetramethyl ethane-1,1,2,2-tetracarboxylate 
• 147425-52-3 1-benzoyl-tetraethyl-1,1,2,2-ethane tetracarboxylate 
• 50708-52-6 1,1,2,2-Tetrakis(methansulfonyloxymethyl)cyclohexan 
• 50708-50-4 1,1,2,2-Tetrakis(hydroxymethyl)cyclohexan 
• 51865-33-9 4,5-Bis-hydroxymethyl-cyclohex-4-ene-1,1,2,2-tetracarbonitrile 
• 51865-34-0 4,5-Bis-hydroxymethyl-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester 
• 33013-92-2 2,3-bis-benzoyloxymethyl-buta-1,3-diene 
• 91766-36-8 2,3-Bisacetoxymethyl-3-butenylacetat 
• 134433-54-8 N,N'-bis-(4-phenylbutyl)-2,3-bis-(4-phenylbutylaminomethyl)-butane-1,4-diamine tetrahydrochloride 

Relevant articles and documents

Atom-economic thiophosphoroselenenylations of C–H acid esters and amides

Three improved thiophosphoroselenenylation procedures of CH-acids, including derivatives of malonic and acetyl-, phosphono-, 4-nitrophenyl- and 3-pyridylacetic acids, have been described and compared to previously reported thiophosphoroselenylation of diethyl malonate using bis(disopropoxyphosphinothioyl)diselenide alone or with the aid of methyl iodide. The use of iodine makes it possible to utilize both equivalents of the selenenylating agent. The procedures work well for the majority of nucleophiles in a pKa range between more acidic malononitrile or Meldrum acid and less acidic phenylacetates. The reaction carried out on diethyl malonate in boiling rectified ethanol yields selenoacetate, which cannot be obtained by direct phosphoroselenenylation. Crystal structure of one of the selenomalonamides confirms the stabilization effects of both carbonyl oxygens on selenium atom. The P-Se bond splitting, using TBAF in 3-molar excess in the presence of alkylating agent yields the respective C,Se-dialkyl derivatives.

Reaction of N-chloroamines with carbanions derived from ethyl acetoacetate and diethyl malonate

Carbanions derived from ethyl 3-oxobutanoate and diethyl malonate reacted with an equimolar amount of N-chloro-N-ethylethanamine, N-chloromorpholine, or N-chloropiperidine to give diethyl 2,3-diacetylbutanedioate and tetraethyl ethane-1,1,2,2-tetracarboxylate in 68–83% yield. The possibility of heterocoupling of ethyl 3-oxobutanoate and diethyl malonate carbanions by the action of N-chloro-N-ethylethanamine and the effect of the molar reactant ratio on the selectivity of oxidative homo- and heterocoupling were studied.

Sequential fullerenylation of bis-malonates-efficient access to oligoclusters with different fullerene building blocks

A method for the sequential fullerenylation of bis-malonates with parent C60 and C2v-symmetric pentakis-adducts is reported. This approach relies on the finding that (a) chloromalonates can be used for the nucleophilic cyclopropanation of [6,6] double bonds of C60, and (b) chloromalonates, in contrast to bromomalonates, do not undergo base-catalyzed halogen exchange reactions. For the proof of concept, we synthesized a heptafullerene by using a divergent approach based on a fullerene hexakis-adduct with six bis-malonate addends in octahedral positions, each of which is suitable for an additional cyclopropanation of a fullerene building block. A sequence for the selective fullerenylation of bis-malonates with C60 and its exohedral C2v-symmetric pentakis-adducts has been developed. This method enables the straightforward synthesis of highly functional fullerene derivatives such as the heptafullerene 1.