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Acetone, oxime

Also known as N-propan-2-ylidenehydroxylamine, Acetone oxime, Acetoxime, 2-Propanone, oxime

Acetone oxime, also called acetoxime or N-propan-2-ylidenehydroxylamine, is an oxime intermediate used in chemical synthesis, analytical studies, and selected industrial formulation research.

Organic chemicals Oximes and nitrogen-containing intermediates
C₃H₇NO
C₃H₇NO

Product identity

CAS number
127-06-0
Molecular formula
C3H7NO
Molecular weight
73.09 g/mol
Category
Organic chemicals
Subcategory
Oximes and nitrogen-containing intermediates
Common aliases
N-propan-2-ylidenehydroxylamine, Acetone oxime, Acetoxime

Product overview

What is Acetone, oxime?

Acetone oxime is an organic oxime identified by CAS number 127-06-0 and the IUPAC name N-propan-2-ylidenehydroxylamine. Its molecular formula is C3H7NO, corresponding to a molecular weight of 73.09. The molecule contains a carbon–nitrogen double bond associated with an oxime functional group, formed from acetone and hydroxylamine. Acetoxime, acetone oxime, 2-propanone oxime, and acetonoxime are recognized names for the same compound.

Acetone oxime is a small, nitrogen-containing molecular reagent whose behaviour reflects both the oxime group and its compact carbon framework. Oximes can participate in condensation chemistry, coordination interactions, and transformations involving the carbon–nitrogen bond. Practical behaviour depends on solvent, concentration, temperature, impurities, and formulation conditions. These variables can influence dissolution, reaction rate, phase behaviour, and compatibility with other ingredients during laboratory or manufacturing work.

In established chemical practice, acetone oxime is chiefly encountered as a research reagent, synthesis intermediate, and subject of analytical or mechanistic study. Oxime chemistry is relevant to derivatization, reduction, rearrangement, and coordination investigations, while related compounds appear in industrial formulations and corrosion-control research. A particular application should be assessed against the intended process, applicable regulations, and the documented characteristics of the selected material.

Selection of acetone oxime should focus on identity, composition, physical form, water content, impurity profile, and compatibility with the proposed reaction or formulation. The most suitable material depends on whether the objective is synthesis, analytical comparison, process development, or educational experimentation. Users should establish their own handling controls, exposure assessment, reaction parameters, and end-use suitability rather than infer performance from the chemical name alone.

Technical profile

Product properties

Review the product identity and general physical profile before specifying the grade required for your operation.

IUPAC name
N-propan-2-ylidenehydroxylamine
Category
Organic chemicals
Subcategory
Oximes and nitrogen-containing intermediates
Molecular formula
C3H7NO
Molecular weight
73.09 g/mol

Uses and markets

Applications and industries

The correct product specification depends on the intended process, grade requirements and operating conditions.

Detailed product information

Detailed Acetone, oxime product information

Molecular identity and oxime functionality

Acetone oxime is the compact oxime derived from acetone, with formula C3H7NO and CAS number 127-06-0. Its hydroxylamine-derived nitrogen–oxygen functionality gives the molecule a distinctive combination of hydrogen-bonding capacity and carbon–nitrogen unsaturation. This structure makes acetone oxime useful for examining how oximes behave in synthesis, analysis, coordination chemistry, and controlled transformation studies. Identity should be confirmed against the intended specification before technical use.

The carbon–nitrogen double bond is central to the chemistry of acetone oxime. Depending on reaction conditions, oximes may undergo hydrolysis, reduction, rearrangement, or conversion into other nitrogen-containing products. Acetone oxime therefore functions not only as a named compound but also as a model substrate for studying reaction selectivity. Solvent choice, acidity, temperature, and water content can substantially affect observed behaviour and should be evaluated experimentally.

Reaction behaviour in synthesis and analysis

Acetone oxime can participate in synthetic investigations in which the oxime group is retained, transformed, or used to probe reaction mechanisms. Its relatively small structure can simplify interpretation of reaction mixtures compared with larger substituted oximes. Researchers may examine conversion under reducing, hydrolytic, or rearrangement conditions, but the outcome depends on the complete reagent system rather than on the compound name alone. Controlled screening is appropriate before scale-up.

In analytical work, acetone oxime may function as a comparison material, reaction substrate, or reference point for methods addressing volatile or polar nitrogen-containing compounds. Method development should consider extraction efficiency, chromatographic response, derivatization requirements, and possible interference from structurally related oximes. A procedure validated for another oxime should not automatically be assumed to provide equivalent recovery or selectivity for acetone oxime.

Acetone oxime compared with related oximes

Acetone oxime differs from aldoximes because its oxime carbon is bonded to two carbon substituents rather than to hydrogen. This ketoxime structure can influence hydrolysis behaviour, rearrangement pathways, steric environment, and analytical response. Compared with larger ketoximes, acetone oxime offers a less substituted framework that may be useful for mechanistic comparison. These distinctions matter when transferring reaction conditions or interpreting data across an oxime series.

Acetone oxime should also be distinguished from acetone oxime methyl ether, in which the oxime hydroxyl hydrogen has been replaced by a methyl group. That structural change removes the oxime O–H donor and alters polarity, hydrogen bonding, and likely reaction behaviour. Data for the ether should therefore not be used as a direct substitute for acetone oxime in formulation, analysis, or synthetic planning without supporting evidence.

Formulation and technical selection considerations

When acetone oxime is incorporated into a reaction or formulation study, the relevant variables include concentration, solvent system, acidity, water activity, temperature, and contact with reactive metals or oxidizing materials. These factors can influence stability and conversion pathways. Compatibility should be assessed in the actual matrix, particularly where other nucleophiles, electrophiles, catalysts, or strong acids and bases are present. Small-scale evaluation can identify unexpected phase or reaction behaviour.

Technical selection should distinguish a material intended for exploratory synthesis from one used for quantitative analytical work. The latter generally requires closer attention to identity confirmation, impurity effects, moisture, and response reproducibility. Acetone oxime may be appropriate for a particular method or reaction, but suitability remains application-specific. Users should establish procedures for exposure control, waste treatment, and reaction quenching based on their own operating conditions and applicable requirements.

Frequently asked questions

Questions about Acetone, oxime

What is acetone oxime used for?

Acetone oxime is used mainly as an organic synthesis intermediate, research reagent, and analytical subject. Its oxime group supports studies involving reaction mechanisms, reduction, hydrolysis, rearrangement, derivatization, and coordination behaviour. It can also serve as a comparison compound when developing methods for nitrogen-containing organic substances. The exact use depends on the selected material, solvent system, reaction conditions, and required purity. A common laboratory use does not automatically establish suitability for manufacturing, formulation, or regulated applications. Users should evaluate the intended process experimentally and apply appropriate exposure controls, waste procedures, and technical review before introducing acetone oxime into a larger operation.

How does the oxime group affect acetone oxime chemistry?

The oxime group gives acetone oxime a carbon–nitrogen double bond together with an N–O linkage and an oxime hydroxyl hydrogen. These features influence polarity, hydrogen bonding, reactivity, and interaction with acids, bases, catalysts, and metal species. Under suitable conditions, oximes can undergo hydrolysis, reduction, rearrangement, or derivatization. The compact structure of acetone oxime makes it useful for observing these transformations without extensive substituent complexity. Reaction behaviour is not fixed solely by molecular identity; solvent, temperature, water content, concentration, and other reagents can change the outcome. Small-scale trials are advisable when developing unfamiliar reaction conditions.

How is acetone oxime different from acetone oxime methyl ether?

Acetone oxime contains an oxime O–H group, whereas acetone oxime methyl ether has that hydrogen replaced by a methyl group. This apparently small change alters hydrogen-bond donation, polarity, solvent interactions, and the compound’s response in analytical or synthetic systems. The ether may show different volatility, extraction behaviour, and reaction selectivity from acetone oxime. Consequently, data generated for the methyl ether should not be treated as interchangeable with data for the parent oxime. Selection between them should follow the specific reaction or analytical objective, supported by compatibility testing and method performance evidence.

Can acetone oxime be used in analytical methods?

Acetone oxime can be considered for analytical work as a reference compound, reaction substrate, or model analyte in studies of oxime chemistry. Method developers may need to examine sample preparation, solvent compatibility, extraction, chromatographic retention, detector response, and possible derivatization. Its behaviour can differ from that of larger or differently substituted oximes, so a method established for another compound may require adjustment. Quantitative use should be supported by appropriate calibration, selectivity, precision, and recovery studies. The compound’s analytical suitability depends on the complete method and matrix, not simply on its presence in a chemical catalogue.

What reactions can acetone oxime undergo?

Acetone oxime can participate in several classes of transformation associated with oxime chemistry. Depending on the reagent environment, researchers may investigate hydrolysis toward carbonyl-related products, reduction of the carbon–nitrogen functionality, rearrangement under suitable activating conditions, or derivatization at the oxime oxygen. Coordination interactions with some metal species may also be relevant in controlled studies. These pathways are highly condition-dependent and should not be assumed to proceed in the same way across solvents or catalysts. Reaction planning should address temperature, acidity, water content, reagent compatibility, heat release, and appropriate analytical monitoring before experimentation.

What factors should be considered when selecting acetone oxime for a formulation or process study?

Selection should begin with confirmation that the material is acetone oxime rather than a related oxime or an ether derivative. The intended work may then require review of composition, moisture, impurity profile, physical form, solvent compatibility, and analytical response. Process conditions such as pH, temperature, concentration, catalysts, oxidants, reducing agents, and contact materials can influence behaviour. Users should assess whether the proposed application needs research-grade characterization, quantitative analytical performance, or process-intermediate suitability. Exposure controls, reaction quenching, waste handling, and applicable local requirements should be established for the actual operating environment rather than inferred from general chemical descriptions.

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