Also known as N-(propan-2-ylideneamino)aniline, Acetone phenylhydrazone, 2-Propanone, phenylhydrazone, 0PV0413LW9
2-Propanone, 2-phenylhydrazone (CAS 103-02-6; C9H12N2) is an organic hydrazone used primarily in chemical research, synthesis and analytical investigations.
Organic chemicalsHydrazones and nitrogen-containing intermediates
2-Propanone, 2-phenylhydrazone is an organic hydrazone with the molecular formula C9H12N2 and molecular weight 148.20. It is also known as acetone phenylhydrazone, 2-propanone phenylhydrazone and N-(propan-2-ylideneamino)aniline. The molecule contains a phenyl group connected through a nitrogen–nitrogen linkage to an isopropylidene unit, giving it a defined nitrogen-rich structure for laboratory and synthetic chemistry work.
As a condensation product of acetone and phenylhydrazine, 2-Propanone, 2-phenylhydrazone belongs to a class whose behaviour is influenced by the hydrazone functional group. Its nitrogen atoms can affect polarity, hydrogen-bonding patterns and reactivity toward selected reagents. The conjugated aromatic portion may contribute to spectroscopic response, while the overall neutral organic structure is generally considered through its solubility, crystallinity and compatibility with the intended solvent system.
2-Propanone, 2-phenylhydrazone is encountered principally in organic chemistry, reaction studies and analytical or educational settings involving carbonyl-derived hydrazones. Such compounds can serve as isolable derivatives in investigations of carbonyl chemistry or as reference materials for method development. A particular use depends on the required purity, physical form, analytical method and applicable laboratory controls; the presence of this compound does not by itself establish suitability for food, pharmaceutical or diagnostic use.
Selection should begin with the intended reaction or measurement rather than with the name alone. Users may need to consider identity confirmation, residual starting materials, water content, solvent compatibility, concentration range and the stability of the hydrazone under the planned conditions. Comparisons with related phenylhydrazones should account for the carbonyl precursor and substitution pattern, because small structural changes can alter chromatographic retention, crystallisation, spectral response and reaction behaviour.
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-ylideneamino)aniline
Category
Organic chemicals
Subcategory
Hydrazones and nitrogen-containing intermediates
Molecular formula
C9H12N2
Molecular weight
148.20 g/mol
Uses and markets
Applications and industries
The correct product specification depends on the intended process, grade requirements and operating conditions.
Detailed 2-Propanone, 2-phenylhydrazone product information
Molecular structure and reactivity
2-Propanone, 2-phenylhydrazone contains a carbon–nitrogen double-bond system formed from acetone and phenylhydrazine, alongside an N–N bond and an aromatic ring. This arrangement distinguishes it from simple amines and from uncondensed carbonyl compounds. The hydrazone nitrogen atoms can participate in protonation, hydrogen bonding and reagent-dependent transformations, while the phenyl substituent can influence electronic distribution and spectroscopic behaviour.
Compared with acetone phenylhydrazone, the name 2-Propanone, 2-phenylhydrazone describes the same core compound rather than a different structural family. In contrast, 2,4-dinitrophenylhydrazones contain strongly electron-withdrawing nitro groups that substantially change polarity, colour and analytical response. These distinctions matter when selecting a derivative for separation, identification or reaction studies, because analogue behaviour cannot be assumed from the shared hydrazone functionality.
Analytical and formulation considerations
For 2-Propanone, 2-phenylhydrazone, analytical method development commonly considers chromatographic retention, ultraviolet response, sample dissolution and possible interference from phenylhydrazine or acetone-derived materials. A practical method may require comparison against an authenticated identity reference, attention to injection-solvent compatibility and assessment of response across the working concentration range. The most suitable technique depends on the purpose, matrix and required selectivity.
In formulation or reaction design, 2-Propanone, 2-phenylhydrazone should be evaluated as a neutral organic compound whose behaviour can change with solvent polarity, acidity, temperature and water exposure. Strongly acidic conditions may promote protonation or hydrolytic changes, while incompatible oxidising or reducing environments may affect the nitrogen-containing structure. These possibilities should be examined experimentally rather than inferred from a related hydrazone.
Role in organic chemistry studies
2-Propanone, 2-phenylhydrazone can provide a convenient defined substrate for examining condensation chemistry, hydrazone formation and transformations of nitrogen–nitrogen-containing molecules. Its use may support teaching demonstrations, reaction screening or preparation of comparative samples. The compound is not interchangeable with a free carbonyl reagent: its carbonyl group has already been converted into a hydrazone, so reaction pathways and reactivity expectations differ.
Relative to acetone itself, 2-Propanone, 2-phenylhydrazone is less representative of a freely available ketone carbonyl and may be selected when an isolable derivative is useful for study. Relative to substituted arylhydrazones, it has no additional ring substituents to provide a deliberate electronic or chromophoric effect. This makes structural comparison valuable when interpreting reaction rates, spectra, melting behaviour or chromatographic separation.
Selection factors for laboratory use
When selecting 2-Propanone, 2-phenylhydrazone, users should align the material with the intended analytical or synthetic objective. Identity testing can include spectroscopic examination, chromatographic assessment and comparison of relevant physical observations. Solvent selection should be checked at the planned concentration, because a solvent that dissolves a small analytical portion may not support a larger reaction charge or prolonged contact.
The compound should also be distinguished from phenylhydrazine, acetone phenylhydrazone analogues and 2,4-dinitrophenylhydrazine derivatives. Those materials differ in functional-group state, substitution and likely analytical response. For 2-Propanone, 2-phenylhydrazone, suitability is therefore grade- and method-dependent, with attention to impurities that could influence derivatisation, reaction conversion, detector response or interpretation of comparative experiments.
Frequently asked questions
Questions about 2-Propanone, 2-phenylhydrazone
What type of compound is 2-Propanone, 2-phenylhydrazone?
2-Propanone, 2-phenylhydrazone is an organic hydrazone formed from acetone and phenylhydrazine. Its structure includes an aromatic phenyl group, an N–N linkage and a carbon–nitrogen double bond associated with the former ketone carbonyl. This places it within nitrogen-containing condensation products rather than simple ketones or primary amines. The compound is commonly considered in organic synthesis, analytical chemistry and research contexts where an isolable carbonyl derivative is useful. Its exact behaviour depends on solvent, acidity, temperature, water content and the presence of other reagents. Structural identity should be confirmed using an appropriate analytical method for the intended work.
How does 2-Propanone, 2-phenylhydrazone differ from acetone?
Acetone is a small ketone with a reactive carbonyl group, whereas 2-Propanone, 2-phenylhydrazone is the corresponding phenylhydrazone derivative. During hydrazone formation, the carbonyl oxygen is replaced within a C=N–N framework connected to a phenyl group. Consequently, the two substances differ in molecular weight, polarity, solubility, spectral response and reaction pathways. Acetone can participate directly in many carbonyl reactions; the hydrazone generally behaves as a more structurally defined nitrogen-containing derivative. A laboratory method designed for acetone should therefore not be assumed suitable for this compound without checking calibration, separation, detection and chemical compatibility.
What is the relationship between this compound and 2,4-dinitrophenylhydrazine derivatives?
Both 2-Propanone, 2-phenylhydrazone and 2,4-dinitrophenylhydrazine-derived products belong to the broad hydrazone family, but they are not interchangeable. The 2,4-dinitrophenyl group contains two nitro substituents that strongly influence electron distribution, polarity, colour and analytical response. 2-Propanone, 2-phenylhydrazone has an unsubstituted phenyl group and already represents the acetone-derived hydrazone product. These structural differences can affect crystallisation, chromatography, spectroscopy and reactivity. A procedure developed for a dinitrophenylhydrazone should therefore be reviewed before adaptation, including reagent proportions, solvent system, detection wavelength and interpretation of any derivative-specific response. The final decision should consider the supplied 2-Propanone, 2-phenylhydrazone specification, intended process and applicable requirements rather than the chemical name alone.
Which analytical approaches may be considered for 2-Propanone, 2-phenylhydrazone?
Analytical evaluation of 2-Propanone, 2-phenylhydrazone may involve chromatography, infrared spectroscopy, nuclear magnetic resonance, mass spectrometry or other suitable identity and purity techniques. The choice depends on whether the objective is confirmation of structure, assessment of related substances, reaction monitoring or measurement in a formulated sample. Chromatographic work should consider dissolution, injection-solvent compatibility, retention and possible phenylhydrazine or acetone-derived impurities. Spectroscopic interpretation should account for the aromatic ring, hydrazone linkage and nitrogen atoms. Method performance must be established for the actual matrix and purpose rather than transferred automatically from a related hydrazone.
Can 2-Propanone, 2-phenylhydrazone be used in organic synthesis?
2-Propanone, 2-phenylhydrazone can be considered for selected organic synthesis studies involving hydrazone chemistry or nitrogen-containing intermediates. Its usefulness depends on the desired transformation, reagent compatibility and the need to preserve or modify the C=N–N framework. It should not be treated as a universal substitute for acetone, phenylhydrazine or another carbonyl derivative, because each has different functional reactivity. Reaction planning should examine acidity, temperature, solvent, water exposure and potential oxidation or reduction pathways. Small-scale compatibility studies are appropriate when the intended transformation has not previously been established for this specific compound.
What factors influence the behaviour of this hydrazone in solution?
The solution behaviour of 2-Propanone, 2-phenylhydrazone can be influenced by solvent polarity, concentration, temperature, acidity and water content. These factors may affect dissolution, protonation state, aggregation, chromatographic response or the balance between intact hydrazone and hydrolysis-related species. Strongly acidic environments may alter nitrogen protonation and can promote changes that are not observed under neutral conditions. Solvent compatibility should therefore be checked at the actual working concentration and contact time. Results from a related phenylhydrazone may provide context, but substitution differences can produce meaningful changes in solubility, stability and analytical response.
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