Diethyl oxalate

Base Information

• Chemical Name: Diethyl oxalate
• CAS No.: 95-92-1
• Molecular Formula: C6H10O4
• Molecular Weight: 146.143
• Hs Code.: 29171900
• European Community (EC) Number: 202-464-1
• NSC Number: 8851
• UN Number: 2525
• UNII: 860M3ZWF6J
• DSSTox Substance ID: DTXSID2044472
• Nikkaji Number: J43.379I
• Wikidata: Q904612
• Metabolomics Workbench ID: 130606
• ChEMBL ID: CHEMBL3183226
• Mol file: 95-92-1.mol

Synonyms:DIETHYL OXALATE;95-92-1;Ethyl oxalate;diethyloxalate;Ethanedioic acid, diethyl ester;Diethyl ethanedioate;Oxalic acid, diethyl ester;Oxalic ether;Oxalic Acid Diethyl Ester;Ethyl oxalate (VAN);NSC 8851;Diethylester kyseliny stavelove;HSDB 2131;EINECS 202-464-1;UN2525;Diethylester kyseliny stavelove [Czech];BRN 0606350;Diethyl ester of oxalic acid;UNII-860M3ZWF6J;860M3ZWF6J;DTXSID2044472;NSC-8851;Ethanedioic acid, 1,2-diethyl ester;EC 202-464-1;4-02-00-01848 (Beilstein Handbook Reference);MFCD00009119;diethyl ethaneioate;Diethyl ethanidioate;Oxalic acid diethyl;diethyl ethane-dioate;ETHYL OXOLATE;oxalic acid diethylester;1,2-diethyl ethanedioate;C2H5OCOCOOC2H5;Diethyl oxalate, >=99%;SCHEMBL7262;WLN: 2OVVO2;DIETHYL OXALATE [MI];DIETHYL OXALATE [HSDB];DIETHYL OXALATE [INCI];CHEMBL3183226;DTXCID0024472;NSC8851;AMY37179;Ethanedioic acid 1,2-diethyl ester;Diethyl oxalate, analytical standard;Tox21_302109;BBL011413;Ethyl oxalate [UN2525] [Poison];NA2525;STL146519;ETHANEDIOC ACID, DIETHYL ESTER;AKOS000120214;Ethyl oxalate [UN2525] [Poison];UN 2525;CAS-95-92-1;NCGC00255767-01;AS-14315;BP-13324;LS-99427;Diethyl oxalate, purum, >=99.0% (GC);FT-0645510;O0078;O0120;EN300-19207;F87445;Q904612;J-802189;Q-200981;5-pentyl-5-tetrahydropyran-2-yl-imidazolidine-2,4-dione;ETHANEDIOIC ACID,DIETHYL ESTER (DIETHYLOXALATE);F1908-0115;Z104473164

Chemical Property of Diethyl oxalate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 1 mm Hg ( 47 °C)
• Melting Point: -41 °C(lit.)
• Refractive Index: n20/D 1.410(lit.)
• Boiling Point: 185.4 °C at 760 mmHg
• Flash Point: 75.6 °C
• PSA: 52.60000
• Density: 1.086 g/cm³
• LogP: 0.11260
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with alcohols, ether and other common organic solvents.
• Water Solubility.: MAY DECOMPOSE
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 146.05790880
• Heavy Atom Count: 10
• Complexity: 114
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Diethyl Oxalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T
• Statements: 22-36-68/21-48/25-35-61-60
• Safety Statements: 23-45-36/37/39-28-26-25-24-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)C(=O)OCC
• Uses: manufacture of phenobarbital, ethylbenzyl malonate, triethylamine, and similar chemicals, plastics, dyestuff intermediates. Solvent for cellulose esters, perfumes. Diethyl oxalate is used to prepare active pharmaceutical ingredients (API), plastics and dyestuff intermediates. It is also used as a solvent for cellulose esters, ethers, resins, perfumes and lacquers for electronics. It is involved in the transesterification reaction with phenol to get dipheny oxalate. It is also involved in the Claisen condensation ketosteroids to prepare glyoxalyl derivatives. Further, it is used to prepare sym-1,4-diphenyl-1,4-dihydro-1,2,4,5-polytetrazine. In addition to this, it is utilized in the microemulsion synthesis of zinc oxide nanoparticles.

Technology Process of Diethyl oxalate

There total 92 articles about Diethyl oxalate 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: 70.0%

cis-(ethyloxalyl)(ethoxycarbonyl)tetracarbonyliron → iron pentacarbonyl (13463-40-6,37220-42-1) + bis(ethoxycarbonyl)tetracarbonyliron + oxalic acid diethyl ester (95-92-1)

Guidance literature:

In dichloromethane-d2; byproducts: CO; introducing a soln. of Fe-complex in CD2Cl2 into NMR tube, maintaining temp. at 28°C under N2; monitoring by (13)C-NMR and gas chromatography;

DOI:10.1016/0022-328X(94)88044-1

Reference yield:

ethanol (64-17-5) + D-glucose (50-99-7) → ethyl 3-furancarboxylate (614-98-2) + malondialdehyde bis(diethyl acetal) (122-31-6) + ethyl 3,3-diethoxypropanoate (10601-80-6) + 4-oxopentanoic acid ethyl ester (539-88-8) + oxalic acid diethyl ester (95-92-1) + diethyl malonate (105-53-3) + diethyl Fumarate (623-91-6) + Ethyl diethoxyacetate (6065-82-3) + Diethyl maleate (141-05-9) + succinic acid diethyl ester (123-25-1)

Guidance literature:

With oxygen; O₄₀PW₁₂^(3-)*Cu⁽²⁺⁾*C₈H₁₅N₂O₃S⁽¹⁺⁾; at 170 ℃; for 4h; under 7500.75 Torr; Autoclave;

DOI:10.1039/d1gc03114g

Reference yield:

ethanol (64-17-5) + cellulose (9004-34-6) → ethyl 3-furancarboxylate (614-98-2) + malondialdehyde bis(diethyl acetal) (122-31-6) + ethyl 3-ethoxypropionate (763-69-9) + ethyl 3,3-diethoxypropanoate (10601-80-6) + 4-oxopentanoic acid ethyl ester (539-88-8) + oxalic acid diethyl ester (95-92-1) + diethyl malonate (105-53-3) + diethyl Fumarate (623-91-6) + Ethyl diethoxyacetate (6065-82-3) + Diethyl maleate (141-05-9) + succinic acid diethyl ester (123-25-1)

Guidance literature:

With oxygen; O₄₀PW₁₂^(3-)*Cu⁽²⁺⁾*C₈H₁₅N₂O₃S⁽¹⁺⁾; at 170 ℃; for 4h; under 7500.75 Torr; Autoclave;

DOI:10.1039/d1gc03114g

upstream raw materials:

Dimethyl oxalate

potassium ethoxide

oxalyl dichloride

ethanol

Downstream raw materials:

2-oxo-2-(piperidin-1-yl)acetic acid

ethyl 2-oxo-2-(piperidine-1-yl)acetate

oxo-(2-oxo-pyrrolidin-3-yl)-acetic acid ethyl ester

oxo-(2-oxotetrahydrofuran-3-yl)acetic acid ethyl ester

Refernces

Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity

10.3762/bjoc.12.159

The research focuses on the first total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity derived from a fungal metabolite. The purpose of the study was to design and execute a synthetic strategy for leopolic acid A, which could potentially lead to the development of new antimicrobial compounds given the growing concern over antibiotic resistance. The synthesis involved crucial steps such as a Dieckmann cyclization to form the 2,3-pyrrolidinedione ring and a Wittig olefination to introduce the polymethylene chain. Key chemicals used in the process included p-methoxybenzylamine, diethyl oxalate, BnBr, K2CO3, DIBAL-H, PPh3, CBr4, n-nonanal, LiHMDS, CAN, and 2-tert-butoxycarbonylamino-3-methylbutyric acid pentafluorophenyl ester, among others. The study concluded that leopolic acid A was successfully synthesized in an 11-step process, despite the instability of several intermediates containing the 2,3-pyrrolidinedione moiety. The synthesized compounds showed antibacterial activity, suggesting their potential as promising candidates for future development in the fight against antibiotic resistance. The research also paved the way for further synthesis of analogues to build a structure–activity relationship profile and optimize the activity.

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