Tetraethyl ethylenetetracarboxylate

Base Information

• Chemical Name: Tetraethyl ethylenetetracarboxylate
• CAS No.: 6174-95-4
• Molecular Formula: C14H20 O8
• Molecular Weight: 316.308
• Hs Code.: 2917190090
• European Community (EC) Number: 228-218-3
• NSC Number: 16084
• UNII: Z4Q32RG79L
• DSSTox Substance ID: DTXSID00210743
• Nikkaji Number: J211.438K
• Wikidata: Q83085508
• Mol file: 6174-95-4.mol

Synonyms:Tetraethyl ethylenetetracarboxylate;6174-95-4;Tetracarbethoxyethylene;Tetraethyl ethenetetracarboxylate;tetraethyl ethene-1,1,2,2-tetracarboxylate;Ethenetetracarboxylic acid, tetraethyl ester;Tetrakis(ethoxycarbonyl)ethylene;Z4Q32RG79L;EINECS 228-218-3;NSC-16084;AI3-28218;C14H20O8;TETRAETHYLETHYLENETETRACARBOXYLATE;1,1,2,2-tetraethyl eth-1-ene-1,1,2,2-tetracarboxylate;UNII-Z4Q32RG79L;SCHEMBL3672314;Tetaethylethylene tetracarboxylate;DTXSID00210743;NSC16084;MFCD00015161;NSC 16084;STK324836;AKOS003211212;NCGC00323655-01;Ethenetetracarboxylic acid tetraethyl ester;FT-0626338;AB01318433-02;2,3-BIS-ETHOXYCARBONYL-BUT-2-ENEDIOIC ACID DIETHYL ESTER;1,1,2,2-ETHENETETRACARBOXYLIC ACID, 1,1,2,2-TETRAETHYL ESTER

Chemical Property of Tetraethyl ethylenetetracarboxylate

Chemical Property:

• Vapor Pressure: 0.000274mmHg at 25°C
• Melting Point: 54-56°C
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 322.7°C at 760 mmHg
• Flash Point: 135°C
• PSA: 105.20000
• Density: 1.185g/cm³
• LogP: 0.53540
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 316.11581759
• Heavy Atom Count: 22
• Complexity: 382

Purity/Quality:

99% ^*data from raw suppliers

TETRAETHYL ETHENETETRACARBOXYLATE Aldrich ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(=C(C(=O)OCC)C(=O)OCC)C(=O)OCC

Technology Process of Tetraethyl ethylenetetracarboxylate

There total 107 articles about Tetraethyl ethylenetetracarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

hydroxy-ethane-1,1,2,2-tetracarboxylic acid tetraethyl ester (266339-39-3) → 1,1,2,2-tetracarboethoxy-ethylene (6174-95-4)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1002/(SICI)1521-3773(20000303)39:5<902::AID-ANIE902>3.0.CO;2-5

Reference yield: 86.0%

diethyl malonate (105-53-3) → 1,1,2,2-tetracarboethoxy-ethylene (6174-95-4)

Guidance literature:

With aluminum oxide; potassium fluoride; iodine; In acetonitrile; for 16h; Ambient temperature; Irradiation;

DOI:10.1080/00397919208021130

Reference yield: 86.0%

Diethyl 2-bromomalonate (685-87-0) → 1,1,2,2-tetracarboethoxy-ethylene (6174-95-4)

Guidance literature:

With sodium hydroxide; for 0.25h; high-speed vibration milling;

DOI:10.1081/SCC-120030320

upstream raw materials:

diethyl 2-chloromalonate

α,α'-dibromo-2,2'-dinitro-bibenzyl

sodium ethanolate

sodium diethylmalonate

Downstream raw materials:

4,5-dimethyl-cyclohex-4-ene-1,1,2,2-tetracarboxylic acid tetraethyl ester

3-Methyl-1-phenyl-2-pyrazolin-4,4,5,5-tetracarbonsaeure-tetraethylester

tetraethyl ethane-1,1,2,2-tetracarboxylate

bromine

Refernces

• 1、 Asahara, Haruyasu,Kawakami, Shu,Yoshioka, Kotaro,Tani, Shinki,Umezu, Kazuto,Nishiwaki, Nagatoshi. "Unsymmetrical tetra-Acceptor-Substituted alkenes as polyfunctionalized building blocks: A divergent synthesis of densely functionalized pyrrolizines". . p. 1715 - 1723. Retrieved 2018.
• 2、 Krapcho,Huyffer. "". . p. 2904. Retrieved 1963.
• 3、 Majewski, Arkadiusz,Przychodzeń, Witold. "Atom-economic thiophosphoroselenenylations of C–H acid esters and amides". . p. 3390 - 3402. Retrieved 2021/11/17.
• 4、 Zhang, Ya-Lin,Guo, Rui-Ting,Luo, Heng,Liang, Xin-Shen,Wang, Xiao-Chen. "Convergent Synthesis of Dihydropyrans from Catalytic Three-Component Reactions of Vinylcyclopropanes, Diazoesters, and Diphenyl Sulfoxide". supporting information. p. 5627 - 5632. Retrieved 2020/07/14.