Also known as Ethyl oxalate, Oxalic ether, Ethyl oxalate (VAN), Diethylester kyseliny stavelove
Diethyl Oxalate, also called Ethyl oxalate, is an oxalic acid diester used chiefly as an organic synthesis intermediate, analytical reagent and specialty formulation component.
Organic chemicalsOxalic acid esters
C₆H₁₀O₄
Product identity
CAS number
95-92-1
Molecular formula
C6H10O4
Molecular weight
146.14 g/mol
Category
Organic chemicals
Subcategory
Oxalic acid esters
Common aliases
Ethyl oxalate, Oxalic ether, Ethyl oxalate (VAN)
Product overview
What is Diethyl Oxalate?
Diethyl Oxalate, also known as Ethyl oxalate or Oxalic ether, is the diethyl ester of oxalic acid. Its chemical identity is represented by CAS number 95-92-1, IUPAC name diethyl oxalate, molecular formula C6H10O4 and molecular weight 146.14. The molecule contains two ester groups joined through an oxalyl unit, giving it a compact, oxygen-rich structure suited to controlled organic transformations and laboratory investigations.
Diethyl Oxalate is a neutral ester that behaves as a combustible organic liquid or solid depending on temperature and product condition, with physical behaviour influenced by purity and handling environment. Its paired ester groups provide useful electrophilic centres in reactions with suitable nucleophiles, while the ethyl substituents affect volatility, solubility and reaction compatibility. It should be evaluated with solvents, catalysts and reactants for each intended process.
In established chemical practice, Diethyl Oxalate is used mainly as a reagent or intermediate in organic synthesis, including routes involving carbon–carbon bond formation and preparation of substituted oxalate-related compounds. It may also support analytical and educational work where an oxalate ester is required. These applications describe recognised chemical roles; suitability for a particular process depends on the formulation, reaction design, equipment and specification selected.
Selection of Diethyl Oxalate should consider the intended reaction mechanism, water sensitivity, solvent system, temperature profile and compatibility with catalysts or bases. Buyers comparing it with dimethyl oxalate should account for the longer ethyl groups, which can alter solubility, volatility and crystallisation behaviour. Practical evaluation should also consider the required impurity profile, physical state at the operating temperature and applicable workplace controls before use.
Technical profile
Product properties
Review the product identity and general physical profile before specifying the grade required for your operation.
Category
Organic chemicals
Subcategory
Oxalic acid esters
IUPAC name
diethyl oxalate
Molecular formula
C6H10O4
Molecular weight
146.14 g/mol
Uses and markets
Applications and industries
The correct product specification depends on the intended process, grade requirements and operating conditions.
Diethyl Oxalate is a symmetrical diester containing two carbonyl groups and two ethoxy groups. This arrangement gives the molecule two ester-derived reaction sites and supports its use in carbon–carbon bond-forming chemistry under appropriate conditions. Compared with simpler monoesters, its adjacent carbonyl architecture creates distinctive reactivity that can be useful when designing oxalate-derived intermediates, screening reaction pathways or studying nucleophilic transformations in controlled laboratory systems.
The ester groups in Diethyl Oxalate can participate in reactions with suitable bases, nucleophiles and reducing systems. Reaction outcome depends strongly on solvent, temperature, stoichiometry, catalyst choice and moisture control. Because related pathways may produce transesterification, cleavage or condensation products, the compound should not be treated as interchangeable with a generic ester. A method-specific assessment is important when selecting Diethyl Oxalate for synthesis or analytical work.
Physical behaviour and handling concepts
Diethyl Oxalate presents physical properties that reflect both its compact oxalate core and ethyl groups. Its appearance, flow behaviour and phase can vary with temperature and composition, so users should consult the applicable product documentation rather than assume a single presentation. The compound is an organic combustible material, and process design should account for ignition sources, ventilation, contact control and compatibility with the surrounding solvent or formulation system.
Solubility and crystallisation behaviour can influence charging, mixing and sampling. Diethyl Oxalate may behave differently from dimethyl oxalate because the ethyl groups increase molecular size and alter intermolecular interactions. That distinction can affect dissolution rates, isolation behaviour and reaction concentration. Small-scale compatibility checks are therefore useful before adopting a solvent system, cooling profile or separation method for a particular synthesis.
Established synthesis roles
Diethyl Oxalate is commonly valued as a carbonyl-rich building block in organic synthesis. Its two ester groups can support transformations that introduce oxalate-derived carbon frameworks or enable subsequent conversion into more complex molecules. Researchers may select it when the ethyl ester form offers useful solubility or reaction behaviour. The exact role depends on the target structure, reagent sequence and conditions established by the process developer.
In comparison with dimethyl oxalate, Diethyl Oxalate can provide a different balance of volatility, solubility and ester cleavage behaviour. Those differences may influence reaction rate, phase separation and work-up, even when the compounds appear structurally similar. A method transferred between the two esters should therefore be re-evaluated rather than assumed equivalent. Diethyl Oxalate is best regarded as a specific reagent with its own process response.
Analytical and formulation considerations
Diethyl Oxalate can be relevant to analytical investigations that examine ester identity, oxalate-related chemistry or reactions with selected amines and other nucleophiles. Interpretation depends on the method, sample matrix and reaction conditions, so an observed response should be linked to a validated procedure rather than a generalised chemical test. Appropriate blanks, controls and instrument suitability help distinguish genuine reaction behaviour from matrix effects or contamination.
For formulation or process development, Diethyl Oxalate should be assessed for compatibility with containers, solvents, catalysts, bases and downstream separation steps. Water content may influence hydrolysis or other competing reactions, while excessive heat can change reaction pathways and handling risk. The required product profile should match the intended use, because an analytical investigation, synthesis route and industrial formulation can impose different impurity and physical-property requirements.
Frequently asked questions
Questions about Diethyl Oxalate
What is Diethyl Oxalate used for in organic synthesis?
Diethyl Oxalate is used primarily as a carbonyl-rich organic intermediate and reagent. Its two ester groups can participate in reactions that build carbon–carbon bonds, introduce oxalate-derived fragments or generate compounds for further transformation. Chemists may choose it when the ethyl ester form provides a useful balance of solubility, reactivity and isolation behaviour. The actual outcome depends on the base, nucleophile, catalyst, solvent, temperature and work-up. It should not be assumed that every reaction reported for dimethyl oxalate will transfer directly. Process developers normally evaluate stoichiometry, moisture sensitivity and competing pathways before selecting Diethyl Oxalate for a particular synthesis.
How does Diethyl Oxalate differ from Dimethyl Oxalate?
Both compounds are oxalic acid diesters, but Diethyl Oxalate contains ethyl groups whereas dimethyl oxalate contains methyl groups. That apparently small structural change can influence molecular weight, volatility, solubility, crystallisation, phase behaviour and reaction work-up. Diethyl Oxalate may offer different compatibility with organic solvents and may separate differently during isolation. Reaction rates and equilibrium behaviour can also change because steric and electronic environments are not identical. Consequently, the two materials should be treated as related but distinct reagents. A method substitution requires experimental confirmation, particularly when solvent concentration, temperature or purification performance is important.
Can Diethyl Oxalate react with amines?
Diethyl Oxalate can react with suitable amines under appropriate conditions because its ester groups are susceptible to nucleophilic attack. Depending on the amine, stoichiometry, solvent, temperature and catalysts, reactions may produce substituted oxamide, aminoester or other condensation products. The outcome is not determined by the name of the amine alone; steric hindrance, basicity, water content and competing pathways can be significant. A test involving Diethyl Oxalate should therefore use a defined procedure, suitable controls and analytical confirmation. Results from an informal screening reaction should not be generalised to every amine, concentration or operating condition.
What physical properties should be considered when using Diethyl Oxalate?
Users should consider Diethyl Oxalate’s phase behaviour, melting or solidification tendency, boiling behaviour, density, solvent compatibility and combustible organic nature. These properties affect transfer, dissolution, mixing, sampling and reaction concentration. Values can vary with temperature and product composition, so operating decisions should rely on the applicable technical and safety documentation for the material selected. Particular attention may be needed when cooling a solution, charging a vessel or changing solvents, because crystallisation or incomplete dissolution can alter effective concentration. Compatibility with equipment, seals and adjacent chemicals should also be assessed for the intended process.
How can Diethyl Oxalate support analytical or educational work?
Diethyl Oxalate can support analytical, teaching and research activities that demonstrate ester reactivity, condensation chemistry, functional-group behaviour or preparation of oxalate-related derivatives. It may also serve as a defined reactant in method development or comparative studies involving related esters. Such work should use a clearly specified procedure, suitable controls and an analytical technique appropriate to the expected products. Demonstrations must account for combustible organic material, chemical exposure and reaction heat. The compound is not a universal indicator or a substitute for a validated analytical reagent, and conclusions should remain limited to the conditions and sample system actually investigated.
What factors affect Diethyl Oxalate reaction performance?
Reaction performance with Diethyl Oxalate is influenced by nucleophile strength, base selection, solvent polarity, temperature, concentration, water content and the relative amounts of reactants. Catalyst choice and mixing can further affect conversion and selectivity, while work-up conditions may influence whether a desired product remains dissolved or crystallises. Because the molecule contains two ester groups, sequential or competing reactions may occur depending on the system. Developers should examine reaction progress with an appropriate analytical method and compare controls when changing materials. Results from one solvent or temperature should not be assumed to predict behaviour in another process.
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