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Acetanilide, also known as Nphenylacetamide, acetanil, or acetanilide is a white to gray solid with molecular formula CH3CONHC6H5.
Acetanilide is an odorless colorless, glossy, crystalline powder or flakes. Acetanilide was the first aniline derivative found to possess analgesic as well as antipyretic properties and was quickly introduced into medical practice.
Acetanilide was established that in the human body it is mostly metabolized to paracetamol, this compound being responsible for the analgesic and antipyretic properties of acetanilide.
CAS Number: 103-84-4
Molecular Formula: C8H9NO
Molecular Weight: 135.16
EINECS Number: 203-150-7
Synonyms: acetanilide, N-Phenylacetamide, 103-84-4, Antifebrin, N-Acetylaniline, Acetanilid, Acetamidobenzene, Acetanil, Acetylaniline, Phenalgene, Acetamide, N-phenyl-, Acetylaminobenzene, Acetic acid anilide, Acetoanilide, Phenalgin, Aniline, N-acetyl-, USAF EK-3, Benzenamine, N-acetyl-, Acetanilidum, Antifebrinum, NSC-7636, SP86R356CC, NSC-203231, CHEBI:28884, RefChem:6369, 203-150-7, 695-031-5, N-acetylarylamine, N-Acetylaminobenzene, AN [Analgesic], NSC 7636, MFCD00008674, Ethananilide, N-Phenyl-acetamide, DTXSID2022543, Acetanilide (Antifebrin), Acetanilide (Acetylaniline), NSC7636, N-Phenylacetamide;N-Phenylacetamide, NCGC00091326-01, ACETYLAMINOBENZENE;ACETANILIDE;AKOS BBS-00004291;'LGC' (4002);'LGC' (2605);'LGC' (2404);PHENYL ACETYLAMINE;Phenalgene
Acetanilide was discovered that it has unacceptable toxic effects, so that acetanilide is no longer used as a drug.
Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and to stabilize cellulose ester varnishes.
Acetanilide is also used in the intermediation of rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis.
Acetanilide is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the sulfa drugs.
Acetanilide is also a precursor in the synthesis of penicillin and other pharmaceuticals.
In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers.
Acetanilide is an organic compound belonging to the aromatic amide family.
It consists of an aniline-derived benzene ring attached to an acetamide group.
Acetanilide is an important laboratory and industrial chemical that has historically been used in pharmaceutical research, dye chemistry, and organic synthesis.
Acetanilide has the molecular formula C₈H₉NO.
Its molecular weight is approximately 135.16 g/mol.
Its CAS Registry Number is 103-84-4.
Acetanilide is also known as N-phenylacetamide.
The name describes the structure in which an acetyl group is attached to the nitrogen atom of aniline.
Other names include acetanilide, acetanil, and N-phenylacetamide.
Acetanilide contains an amide functional group.
The nitrogen is directly bonded to a carbonyl carbon, giving the molecule the characteristic properties of an aromatic amide.
This amide functionality also makes acetanilide less basic than aniline.
Acetanilide contains one benzene ring.
The aromatic ring contributes to its relatively rigid and planar molecular structure.
Acetanilide aromatic character also influences its solubility, melting point, and spectroscopic properties.
Acetanilide is normally a white to colorless crystalline solid.
Acetanilide has a characteristic crystalline appearance when sufficiently pure.
The solid form makes it convenient for laboratory purification and characterization experiments.
Acetanilide has a melting point of approximately 114 °C.
Acetanilide well-defined melting behavior makes it a classic compound for recrystallization experiments.
A narrow melting range can also be used as an indication of sample purity.
Acetanilide has relatively low solubility in cold water.
Acetanilide solubility increases significantly when the temperature is raised.
This difference in solubility is the basis of its common use in recrystallization demonstrations.
Acetanilide is moderately soluble in several organic solvents.
Acetanilide solubility depends strongly on solvent polarity and temperature.
This behavior makes it useful for demonstrating solvent selection in organic purification.
Acetanilide can be synthesized by acetylation of aniline.
In this reaction, the amino group of aniline reacts with an acetylating reagent to form the amide.
Common acetylating reagents include acetic anhydride and acetyl chloride.
Acetanilide synthesis is a classic example of nucleophilic acyl substitution.
The nitrogen atom of aniline attacks the electrophilic carbonyl carbon of the acetylating reagent.
After elimination and proton-transfer steps, the amide product acetanilide is formed.
Acetanilide is commonly used in undergraduate organic chemistry laboratories.
Students can prepare it from aniline and then purify it by recrystallization.
The experiment demonstrates amide formation, purification, melting-point determination, and yield calculation.
Acetanilide is used as a model compound in organic synthesis.
Its amide group can undergo hydrolysis and other chemical transformations under appropriate conditions.
This makes it useful for studying the reactivity of aromatic amides.
Acetanilide can undergo hydrolysis to produce aniline and acetic acid.
The amide bond can be cleaved under sufficiently strong acidic or basic conditions.
Acetanilide is useful for demonstrating the relative stability of amide functional groups.
Acetanilide can undergo electrophilic aromatic substitution.
The acetamido group influences the electronic properties of the benzene ring and directs substitution predominantly toward the para position under suitable conditions.
This behavior makes acetanilide useful in aromatic substitution studies.
Acetanilide can be used as a protected form of aniline in organic synthesis.
Acetylation reduces the strong reactivity and basicity of the free amino group.
The protecting group can later be removed through hydrolysis to regenerate aniline.
Acetanilide is therefore useful for demonstrating amine protection chemistry.
The conversion of aniline to acetanilide temporarily modifies the reactivity of the amino group.
Subsequent deacetylation restores the original amine functionality.
Acetanilide has historical pharmaceutical importance.
It was introduced in the nineteenth century as an analgesic and antipyretic compound.
However, its use as a therapeutic drug declined because safer alternatives became available.
Acetanilide was historically used to reduce pain and fever.
Its pharmacological activity led to its early use as an analgesic and antipyretic.
Its medical use is now primarily of historical significance rather than routine modern therapy.
Acetanilide is chemically related to several important pharmaceutical compounds.
The acetanilide structure provided a foundation for the development and study of other anilide-type analgesics.
Examples include phenacetyl-related compounds and other substituted acetanilides.
Acetanilide is used as an intermediate in chemical synthesis.
Its aromatic amide structure can be modified through substitution, hydrolysis, reduction, and other reactions.
Acetanilide makes it useful for preparing substituted aromatic compounds in research.
Acetanilide has been used in dye and pigment chemistry.
Acetanilide can serve as an intermediate for preparing substituted aromatic compounds used in color chemistry.
Its predictable aromatic substitution behavior makes it useful in synthetic routes.
Acetanilide is used in analytical chemistry as a reference compound.
Acetanilide known melting point, molecular mass, and spectroscopic properties make it suitable for identification and method development.
It can be analyzed by techniques such as HPLC, GC-MS, FTIR, and NMR.
Acetanilide is commonly characterized by infrared spectroscopy.
The spectrum contains characteristic absorptions associated with the amide carbonyl and N–H bond.
These signals help distinguish acetanilide from aniline and other aromatic compounds.
Acetanilide is commonly characterized by nuclear magnetic resonance spectroscopy.
Acetanilide aromatic protons and acetyl methyl group produce characteristic signals in the proton NMR spectrum.
NMR can therefore provide useful confirmation of its molecular structure and purity.
Acetanilide is used in recrystallization experiments because of its temperature-dependent solubility.
It dissolves more readily in hot water than in cold water under appropriate conditions.
Slow cooling can therefore allow relatively pure acetanilide crystals to form while some impurities remain dissolved.
Acetanilide is a useful model for studying intermolecular interactions in crystals.
Acetanilide amide group can participate in hydrogen bonding between molecules.
These interactions contribute to its crystalline structure and physical properties.
Acetanilide is not highly volatile under normal laboratory conditions.
Acetanilide solid crystalline form and relatively high melting point limit evaporation at room temperature.
However, dust exposure can occur when the solid is powdered or handled mechanically.
Acetanilide is an important reference compound in organic chemistry.
Its simple structure combines an aromatic ring with a well-defined amide functionality.
This makes it useful for teaching synthesis, purification, spectroscopy, reaction mechanisms, and functional-group chemistry.
Acetanilide is best described as an aromatic amide with major importance in organic chemistry.
Acetanilide is used as a laboratory model compound, synthetic intermediate, analytical reference material, and historically important pharmaceutical compound.
Its combination of simple structure, characteristic melting point, and predictable chemical reactivity makes it one of the classic compounds encountered in organic chemistry.
Melting point: 113-115 °C (lit.)
Boiling point: 304 °C (lit.)
Density: 1.121 g/cm3
Bulk density: 370 kg/m3
Vapor density: 4.65 (vs air)
Vapor pressure: 1 mm Hg (114 °C)
Refractive index: 1.5700 (estimate)
Flash point: 173 °C
Storage temp.: Store below +30 °C
Solubility: Slightly soluble in water; very soluble in ethanol and acetone; soluble in ethyl ether
Form: Powder
pKa: 0.5 (25 °C)
Color: Off-white to beige to grayish-blue
pH: 5-7 (10 g/L, H2O, 25 °C)
Water solubility: 5 g/L (25 °C)
Merck: 14,50
BRN: 606468
Henry's Law Constant: 4.7×10² mol/(m³Pa) at 25 °C, Yaws (2003)
Dielectric constant: 2.9 (22.0 °C)
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, caustics, and alkalies.
Cosmetics Ingredients Functions: FRAGRANCE; PERFUMING
InChI: InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
InChIKey: FZERHIULMFGESH-UHFFFAOYSA-N
SMILES: CC(=O)Nc1ccccc1
LogP: 1.160
Acetanilide is a member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.
Acetanilide has a role as an analgesic.
It is a member of acetamides and an anilide.
Acetanilide is functionally related to an acetic acid.
Acetanilide is mainly used as an intermediates in the synthesis of pharmaceuticals and dyes, as an additive for hydrogen peroxide and cellulose ester varnishes, and as a plasticizer in polymer industry as well as accelerator in the rubber industry.
Acetanilide is prepared from aniline by acetylating it with acetic anhydride in presence of glacial acetic acid.
Aniline reacts with acetic anhydride to form Acetanilide by nucleophilic substitution reaction and the reaction is called acetylation.
Acetanilide has a relatively planar molecular structure.
The amide group is conjugated with the benzene ring, allowing electron density to be delocalized across part of the molecule.
This conjugation contributes to the restricted rotation and characteristic electronic properties of acetanilide.
Acetanilide exhibits resonance within its amide group.
The nitrogen lone pair can interact with the carbonyl group, giving the C–N bond partial double-bond character.
Acetanilide resonance contributes to the relatively low basicity and chemical stability of the amide nitrogen.
Acetanilide is considerably less basic than aniline.
In acetanilide, the nitrogen lone pair is delocalized toward the carbonyl group rather than being freely available for protonation.
Acetanilide is important when comparing the chemical behavior of aniline and acetanilide.
Acetanilide has a relatively strong amide bond.
The resonance stabilization of the amide group makes the molecule more resistant to many reactions than simple amines.
More vigorous acidic or basic conditions are generally required for efficient hydrolysis.
Acetanilide can be hydrolyzed under acidic conditions.
Acid-catalyzed hydrolysis ultimately produces aniline and acetic acid.
This reaction is commonly used to demonstrate conversion between an amide and its corresponding amine.
Acetanilide can also undergo alkaline hydrolysis.
Strong bases can promote cleavage of the amide bond to produce aniline and acetate-containing products.
Heating is often required because amides are relatively resistant to hydrolysis.
Acetanilide can be reduced to other nitrogen-containing compounds.
Suitable reducing systems can alter the carbonyl-containing amide functionality.
The exact products depend on the reducing reagent and reaction conditions.
Acetanilide can undergo nitration on its aromatic ring.
The acetamido group is an ortho/para-directing substituent in electrophilic aromatic substitution.
Under controlled nitration conditions, the para-substituted product is generally favored because of steric effects.
Acetanilide can therefore serve as a precursor to p-nitroacetanilide.
This reaction is a classic example of electrophilic aromatic substitution in organic chemistry.
The product can subsequently be transformed into other aromatic compounds through additional reactions.
Acetanilide can undergo bromination of the aromatic ring.
The electron-donating resonance effect of the acetamido group activates the ring toward electrophilic substitution relative to strongly deactivating groups.
Controlled conditions can favor substitution at the para position.
Acetanilide can be used to demonstrate regioselectivity.
The acetamido substituent influences where electrophilic substitution occurs on the benzene ring.
Acetanilide makes the compound useful for teaching the relationship between substituent electronic effects and product distribution.
Acetanilide can be used as a protected aniline derivative in multistep synthesis.
Protection of the amino group reduces its nucleophilicity and changes its behavior during subsequent reactions.
The acetyl group can later be removed to regenerate the free amine.
Acetanilide is useful when selective aromatic substitution is required.
Direct reactions of aniline can sometimes be complicated by the strong activating and basic nature of the amino group.
Converting aniline into acetanilide provides greater control over certain synthetic transformations.
Acetanilide can be deacetylated to regenerate aniline.
Hydrolysis removes the acetyl group from the nitrogen atom.
This reversible protection strategy is widely used in synthetic organic chemistry.
Acetanilide can be used as a precursor for substituted aniline derivatives.
Aromatic substitution can first be performed on the protected compound before the amide group is hydrolyzed.
This provides a practical route to certain substituted aromatic amines.
Acetanilide has useful crystal-forming properties.
Its molecules can organize into an ordered crystalline lattice through intermolecular interactions.
Acetanilide contributes to the formation of well-defined crystals during recrystallization.
Acetanilide is sensitive to the choice of recrystallization solvent.
A suitable solvent should dissolve the compound efficiently when hot but poorly when cold.
Water is commonly used in teaching laboratories because acetanilide shows a useful temperature-dependent solubility profile.
Acetanilide recrystallization can demonstrate impurity removal.
When a hot saturated solution is cooled slowly, acetanilide crystallizes while some soluble impurities remain in the liquid phase.
Filtration then separates the purified crystals from the remaining mother liquor.
Acetanilide is frequently used to demonstrate percent recovery.
The mass of purified crystals can be compared with the initial amount of material used.
This provides a simple way to evaluate losses during dissolution, filtration, washing, and drying.
Acetanilide is frequently used to demonstrate melting-point analysis.
A purified sample should exhibit a relatively narrow melting range close to the expected value.
Impurities generally depress and broaden the observed melting range.
Acetanilide can be used for mixed-melting-point experiments.
A sample can be mixed with an authentic reference compound to determine whether the two substances are identical.
A significant depression or broadening of the melting range can indicate that the compounds are different.
Acetanilide has characteristic infrared absorption bands.
Its amide carbonyl produces a strong absorption in the carbonyl region of the IR spectrum.
The N–H stretching vibration provides an additional diagnostic feature.
Acetanilide has characteristic proton NMR signals.
The acetyl methyl group appears as a distinct signal, while the aromatic protons occur in the aromatic region.
The amide N–H proton can also provide a characteristic downfield signal depending on the solvent and conditions.
Acetanilide has characteristic carbon NMR signals.
The carbonyl carbon produces a signal in the downfield region associated with amide carbonyls.
The aromatic carbons and methyl carbon provide additional structural information.
Acetanilide can be analyzed by mass spectrometry.
Acetanilide molecular ion and characteristic fragmentation pattern can support identification.
Mass spectrometry is particularly useful when acetanilide is present in complex mixtures.
Acetanilide can be separated using chromatographic techniques.
Thin-layer chromatography can be used for rapid qualitative monitoring of reactions involving acetanilide.
HPLC can provide more precise separation and quantitative analysis.
Acetanilide has been used as a model compound in environmental chemistry.
Researchers can investigate its degradation, transformation, adsorption, and transport behavior.
Acetanilide relatively simple structure makes it useful for studying the environmental fate of aromatic amides.
Acetanilide can undergo biodegradation under suitable environmental conditions.
Microorganisms can transform the compound through enzymatic pathways involving the aromatic ring and amide functionality.
The rate and extent of degradation depend strongly on environmental conditions.
Acetanilide can undergo photochemical transformation.
Exposure to light in the presence of suitable reactive species can promote chemical changes.
Such processes are relevant to studies of organic contaminants in surface waters.
Acetanilide is relevant to studies of pharmaceutical metabolites and aromatic amides.
Its relatively simple structure provides a model for investigating how aromatic amide compounds are transformed biologically.
These studies can involve hydrolysis, oxidation, and conjugation pathways.
Acetanilide has historical significance in medicinal chemistry.
Its early analgesic use demonstrated that aromatic amides could possess pharmacological activity.
Subsequent research helped establish relationships between chemical structure and therapeutic effects.
Acetanilide contributed to the development of safer analgesic compounds.
Its therapeutic limitations encouraged researchers to investigate structurally related molecules with improved safety profiles.
This work contributed to the broader development of modern analgesic and antipyretic chemistry.
Acetanilide remains valuable despite its limited modern therapeutic use.
Its importance today is largely associated with organic synthesis, teaching, analytical chemistry, and chemical research.
Acetanilide simple structure and predictable reactions make it particularly useful as a model aromatic amide.
Uses:
Acetanilide is used as an intermediate in the synthesis of rubber accelerator, dyes and camphor.
Acetanilide is also used in the synthesis of penicillin and other pharmaceutical products.
Acetanilide is involved in the preparation of 4-acetamidobenzenesulfonyl chloride, which is an intermediate during the synthesis of sulfa drugs.
Further, it is employed as a experimental photographic developer.
In addition to this, it is used to stabilize cellulose ester varnishes.
Acetanilide is widely used as a laboratory model compound in organic chemistry.
Acetanilides well-defined structure makes it suitable for demonstrating amide chemistry, aromatic substitution, and functional-group transformations.
It is especially common in undergraduate laboratory experiments.
Acetanilide is used in recrystallization experiments.
Its solubility changes significantly with temperature, allowing students to dissolve it in hot solvent and recover crystals during cooling.
This makes it a classic example for demonstrating purification by recrystallization.
Acetanilide is used for melting-point determination.
Its relatively sharp melting range provides a convenient reference for evaluating the identity and purity of a synthesized sample.
A depressed or broadened melting range can indicate the presence of impurities.
Acetanilide is used in the synthesis of aromatic amides.
Acetanilide serves as a simple example of how an amine can be converted into an amide through acetylation.
The reaction is useful for teaching nucleophilic acyl substitution.
Acetanilide is used as a protected form of aniline in organic synthesis.
Acetylation temporarily reduces the reactivity and basicity of the amino group.
The protecting group can subsequently be removed by hydrolysis to regenerate aniline.
Acetanilide is used to control the reactivity of aniline during aromatic substitution.
Protection of the amino group makes certain electrophilic aromatic substitution reactions easier to control.
This strategy is particularly useful when selective ortho or para substitution is desired.
Acetanilide is used in the preparation of p-nitroacetanilide.
Controlled nitration of acetanilide provides an important example of electrophilic aromatic substitution.
The product can subsequently be converted into other substituted aromatic compounds.
Acetanilide is used in the preparation of substituted aniline derivatives.
Aromatic substitution can be performed while the amino group remains protected as an acetamide.
Subsequent deacetylation provides the corresponding substituted aniline.
Acetanilide is used in bromination studies.
Acetanilide activated aromatic ring provides a useful system for examining electrophilic bromination and regioselectivity.
The reaction demonstrates how substituents influence the position of aromatic substitution.
Acetanilide is used in organic reaction-mechanism studies.
Acetanilide provides examples of amide resonance, nucleophilic acyl substitution, electrophilic aromatic substitution, and hydrolysis.
These reactions make it useful for demonstrating several fundamental concepts using one compound.
Acetanilide is used as an intermediate in chemical synthesis.
Its aromatic amide structure can be transformed into different substituted aromatic compounds.
The compound therefore serves as a useful starting material in laboratory-scale synthetic routes.
Acetanilide is used in pharmaceutical research.
Acetanilide is not a common modern therapeutic drug, its structure has historical and chemical relevance to anilide-type pharmaceuticals.
Researchers can use it as a reference structure when studying related analgesic compounds.
Acetanilide was historically used as an analgesic.
It was introduced as a pain-relieving medicine during the nineteenth century.
Acetanilide clinical use subsequently declined because of toxicity concerns and the availability of safer alternatives.
Acetanilide was historically used as an antipyretic.
Its ability to reduce fever contributed to its early pharmaceutical importance.
Acetanilide application is mainly of historical interest rather than routine medical use.
Acetanilide is used as a reference compound in analytical chemistry.
Its known physical and spectroscopic properties make it useful for identification and method development.
Acetanilide can be characterized using HPLC, GC-MS, FTIR, NMR, and other analytical techniques.
Acetanilide is used as a reference material for spectroscopic studies.
Its characteristic IR and NMR signals provide recognizable features for structural analysis.
This makes it useful for teaching and validating analytical measurements.
Acetanilide is used in chromatography experiments.
Acetanilide can be separated and identified using techniques such as thin-layer chromatography and HPLC.
These applications help demonstrate retention, separation, and compound identification.
Acetanilide is used in environmental chemistry research.
Researchers use it as a model aromatic amide when investigating degradation, adsorption, and transformation processes.
Its relatively simple molecular structure makes environmental reaction pathways easier to study.
Acetanilide is used in biodegradation studies.
Acetanilide transformation by microorganisms can be investigated under different environmental conditions.
These studies provide information about the fate of aromatic amide compounds in natural and engineered systems.
Acetanilide is used in photochemical degradation studies.
Researchers can investigate how light-driven reactions transform the molecule in aqueous or other environmental systems.
This can provide insight into the behavior of aromatic organic compounds exposed to sunlight.
Acetanilide is used as a model compound in chemical kinetics experiments.
Acetanilide reactions can be monitored over time to investigate reaction rates and mechanisms.
This makes it useful for demonstrating how temperature, concentration, and catalysts influence chemical reactions.
Acetanilide is used in studies of amide hydrolysis.
Its conversion into aniline and acetic-acid-derived products provides a straightforward example of amide bond cleavage.
This reaction can be investigated under acidic or alkaline conditions.
Acetanilide is used in educational demonstrations of functional-group protection.
Students can compare the chemical behavior of aniline before and after acetylation.
This demonstrates how temporary modification of a functional group can improve selectivity in multistep synthesis.
Acetanilide is used in purity-analysis experiments.
Recrystallized samples can be evaluated through melting point, chromatography, and spectroscopic measurements.
These techniques allow students and researchers to compare crude and purified materials.
Acetanilide is used in pharmaceutical and chemical reference collections.
Its historical significance and well-characterized properties make it useful as a reference substance.
Acetanilide can be maintained as a standard for identification and educational purposes.
Acetanilide is used in research involving aromatic amide chemistry.
Its simple molecular structure provides a convenient starting point for studying the behavior of aromatic amides.
Researchers can modify the phenyl ring or amide functionality to investigate structure–property relationships.
Acetanilide is used mainly for research, education, and chemical synthesis today.
Its historical pharmaceutical applications are no longer its principal role because safer therapeutic alternatives are available.
Its greatest current value comes from its predictable chemistry, characteristic physical properties, and usefulness as a reference compound.
Acetanilide is used as a starting material for preparing substituted aromatic compounds.
The benzene ring can undergo controlled electrophilic substitution while the amino group remains protected as an acetamide.
This makes acetanilide useful in multistep organic synthesis.
Acetanilide is used in the preparation of p-aminoacetanilide derivatives.
Aromatic substitution followed by appropriate reduction or deprotection can provide useful substituted anilines.
These transformations are relevant to laboratory synthesis and medicinal chemistry research.
Acetanilide is used in studies of nitration selectivity.
Its acetamido group directs electrophilic substitution toward the ortho and para positions.
The preferential formation of para-substituted products makes it a useful teaching example of steric and electronic effects.
Acetanilide is used in studies of aromatic reduction chemistry.
Nitro-substituted derivatives of acetanilide can be reduced to corresponding amino derivatives.
This provides a convenient route for demonstrating sequential functional-group transformations.
Acetanilide is used in multistep synthesis experiments.
Students can perform acetylation, aromatic substitution, reduction, and hydrolysis as interconnected reactions.
This allows several fundamental organic chemistry concepts to be demonstrated using related compounds.
Acetanilide is used to demonstrate reaction selectivity in organic chemistry.
The acetamido group modifies the electronic density of the aromatic ring and influences where reactions occur.
Acetanilide makes the compound particularly useful for studying substituent effects.
Acetanilide is used in studies of protecting-group strategies.
The amino group can be temporarily protected before reactions are performed elsewhere on the molecule.
The acetyl group can then be removed when the free amine is required.
Acetanilide is used to compare protected and unprotected amines.
Aniline and acetanilide have different basicity, nucleophilicity, and aromatic substitution behavior.
Comparing the two compounds helps illustrate how functional-group protection changes molecular reactivity.
Acetanilide is used in solvent-selection experiments.
Its different solubilities in water and organic solvents allow researchers to investigate solvent polarity and temperature effects.
These properties are particularly useful when designing recrystallization procedures.
Acetanilide is used in fractional crystallization studies.
Differences in solubility between acetanilide and selected impurities can be exploited to obtain purified crystals.
This provides an example of how physical-property differences can be used for chemical separation.
Acetanilide is used in studies of crystal growth.
Controlled cooling of a saturated solution can produce well-defined acetanilide crystals.
The resulting crystals can be examined for morphology, purity, and crystal structure.
Acetanilide is used in X-ray diffraction studies.
Its crystalline nature makes it suitable for investigating molecular arrangement in the solid state.
X-ray diffraction can provide information about unit-cell dimensions and molecular packing.
Acetanilide is used as a solid-state chemistry reference compound.
Its known crystal structure and physical properties make it useful when studying intermolecular interactions.
Hydrogen bonding involving the amide group is particularly relevant to its crystal packing.
Acetanilide is used in calibration and method-development studies.
A known quantity of acetanilide can be used to evaluate the response of analytical instruments.
This is particularly useful when developing chromatographic or spectroscopic methods.
Acetanilide is used in HPLC method-development experiments.
Its chromatographic behavior can be investigated under different mobile-phase conditions.
This helps demonstrate the relationship between molecular properties and chromatographic retention.
Acetanilide is used in GC-MS research and analytical demonstrations.
Its molecular mass and characteristic fragmentation pattern provide recognizable analytical signals.
These features make it useful for teaching mass-spectrometric identification.
Acetanilide is used in quantitative analytical chemistry.
Safety Profile:
Acetanilide can be harmful if swallowed in significant quantities.
Ingestion may cause systemic effects because the compound can be absorbed through the gastrointestinal tract.
Accidental ingestion should therefore be avoided, and contaminated hands should never be used to handle food or beverages.
Acetanilide can cause irritation following direct contact.
The solid or its dust can irritate the eyes, skin, and respiratory tract in susceptible individuals.
Appropriate laboratory hygiene and personal protective equipment should be used during handling.
Acetanilide dust can irritate the respiratory system.
Weighing, grinding, transferring, or otherwise disturbing the solid can generate airborne particles.
Operations that produce dust should therefore be performed with effective local ventilation.
Acetanilide can cause eye irritation.
Contact with the solid or airborne particles may result in redness, discomfort, watering, or inflammation.
Safety glasses or chemical splash goggles should be worn when handling the material.
Acetanilide can cause skin irritation in some individuals.
Repeated or prolonged contact may produce dryness, redness, or discomfort.
Protective gloves should therefore be worn when there is a possibility of direct contact.
Acetanilide can be absorbed through the body after exposure.
Although its dermal absorption is not generally the primary exposure route, prolonged contact should still be avoided.
Good laboratory practice should be used to prevent unnecessary exposure.
Acetanilide can cause systemic toxicity at sufficiently high exposure levels.
Historically, excessive exposure was associated with adverse effects involving the blood and other organs.
Laboratory personnel should therefore avoid treating the substance as harmless simply because it is a common teaching compound.
Acetanilide can affect the blood at sufficiently high doses.
Acetanilide metabolism can produce compounds capable of interfering with normal hemoglobin function.
High exposure may therefore contribute to effects associated with reduced oxygen-carrying capacity.
