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Diethyl oxalate

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Identification
Molecular formula
C6H10O4
CAS number
95-92-1
IUPAC name
diethyl oxalate
State
State

Diethyl oxalate is a liquid at room temperature but can solidify upon cooling. It is typically handled in its liquid form in industrial and laboratory settings.

Melting point (Celsius)
-31.50
Melting point (Kelvin)
241.65
Boiling point (Celsius)
184.00
Boiling point (Kelvin)
457.15
General information
Molecular weight
146.14g/mol
Molar mass
146.1410g/mol
Density
1.0783g/cm3
Appearence

Diethyl oxalate is a colorless to pale yellow liquid. It has a mild, pleasant odor and can form crystals upon cooling below its melting point. It is often used in organic synthesis and has a greasy texture when in liquid form.

Comment on solubility

Solubility of Diethyl Oxalate

Diethyl oxalate, with the chemical formula C6H10O4, presents interesting solubility characteristics that are of significant interest in various chemical applications. Understanding its solubility can be summarized as follows:

  • Solvent Interaction: Diethyl oxalate is soluble in organic solvents such as ethanol, ether, and chloroform, making it versatile for reactions in organic synthesis.
  • Water Solubility: It exhibits limited solubility in water, primarily due to its non-polar nature stemming from the ethyl groups that hinder substantial hydrogen bonding with water molecules.
  • Temperature Dependency: The solubility may change with temperature; generally, higher temperatures can increase solubility in organic solvents due to enhanced kinetic energy of molecules.

These characteristics highlight the importance of solvent choice when working with diethyl oxalate in laboratory settings. Remember that while it is relatively non-polar, it’s crucial to consider the nature of solvents to ensure effective dissolution and reactivity in chemical processes.


Interesting facts

Interesting Facts about Diethyl Oxalate

Diethyl oxalate is a fascinating compound with a variety of unique properties and applications. As an ester derived from oxalic acid, its structure and reactivity give rise to interesting chemical behaviors.

Key Features

  • Versatile Reagent: Diethyl oxalate is commonly used in organic synthesis, particularly in the preparation of various esters. Its reactivity makes it a valuable building block in the synthesis of complex molecules.
  • Intermediary Compound: This compound serves as an intermediary in the production of many pharmaceuticals, agricultural chemicals, and dyes, showcasing its wide-reaching utility in the chemical industry.
  • Decarboxylation: Upon heating, diethyl oxalate can undergo decarboxylation—a process where carbon dioxide is released—resulting in a range of substituted compounds that are of great interest in synthetic chemistry.

Applications and Uses

Diethyl oxalate finds a myriad of applications in different fields:

  • Pharmaceuticals: It plays a role in the synthesis of active ingredients for medications.
  • Agricultural Chemicals: Used in creating pesticides and herbicides that are essential for modern agriculture.
  • Laboratory Research: Often used in chemical education and research as a reagent in various experiments.

Safety and Handling

While diethyl oxalate is a powerful tool in the lab, it is important to note that proper safety precautions should be observed when handling it. This means using gloves, goggles, and working in a well-ventilated area to avoid exposure to vapors.

In conclusion, diethyl oxalate exemplifies the intersection of utility and complexity in organic chemistry. The processes involved in its reactions lead to exciting developments in both theoretical and applied chemistry, making it a compound worth knowing for any serious chemistry student or scientist!

Synonyms
DIETHYL OXALATE
95-92-1
Ethyl oxalate
diethyloxalate
Ethanedioic acid, diethyl ester
Diethyl ethanedioate
Oxalic ether
Oxalic acid, diethyl ester
Oxalic Acid Diethyl Ester
Ethyl oxalate (VAN)
NSC 8851
Diethylester kyseliny stavelove
HSDB 2131
EINECS 202-464-1
UNII-860M3ZWF6J
Diethyl ester of oxalic acid
MFCD00009119
UN2525
Diethylester kyseliny stavelove [Czech]
BRN 0606350
860M3ZWF6J
DTXSID2044472
ETHYL OXOLATE
NSC-8851
C2H5OCOCOOC2H5
Ethanedioic acid, 1,2-diethyl ester
DIETHYL OXALATE [MI]
DIETHYL OXALATE [HSDB]
DTXCID0024472
EC 202-464-1
4-02-00-01848 (Beilstein Handbook Reference)
ETHANEDIOC ACID, DIETHYL ESTER
UN 2525
diethyl ethane-dioate
oxalic acid diethylester
1,2-diethyl ethanedioate
Diethyl oxalate, >=99%
SCHEMBL7262
WLN: 2OVVO2
DIETHYL OXALATE [INCI]
CHEMBL3183226
NSC8851
Diethyl oxalate, analytical standard
Tox21_302109
BBL011413
STL146519
Ethyl oxalate [for Spectrophotometry]
AKOS000120214
Ethyl oxalate [UN2525] [Poison]
FD03598
CAS-95-92-1
NCGC00255767-01
AS-14315
BP-13324
Diethyl oxalate, purum, >=99.0% (GC)
NS00009607
O0078
O0120
EN300-19207
F87445
Q904612
ETHANEDIOIC ACID,DIETHYL ESTER (DIETHYLOXALATE)
5-pentyl-5-tetrahydropyran-2-yl-imidazolidine-2,4-dione
ETHANEDIOIC ACID,DIETHYL ESTER (DIETHYLOXALATE)
F1908-0115
Z104473164
202-464-1
Ethanedioic Acid 1,2-Diethyl Ester; Oxalic Acid Diethyl Ester; Diethyl Ethanedioate; Ethyl Oxalate; NSC 8851