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N-Phenylglycine consists of a phenyl group attached to the nitrogen atom of glycine.
N-Phenylglycine can be represented as C₆H₅NHCH₂COOH, giving it both an aromatic amine functionality and a carboxylic acid group.
N-Phenylglycine combination gives the molecule useful reactivity for organic synthesis and industrial chemical transformations.
CAS Number: 103-01-5
Molecular Formula: C8H9NO2
Molecular Weight: 151.16
EINECS Number: 203-070-2
Synonyms: N-Phenylglycine, 103-01-5, Anilinoacetic acid, CHEBI:55477, 37YJW036TP, DTXSID2047016, RefChem:830994, DTXCID0027016, 203-070-2, 2-(phenylamino)acetic acid, 2-anilinoacetic acid, Glycine, phenyl-, (Phenylamino)acetic acid, Glycine, N-phenyl-, N-phenyl glycine, N-Phenylaminoacetic acid, MFCD00014009, n-phenyl-glycine, BIDD:GT0243, AI3-09070, P0180, Q22668730, Ph-Gly-OH, UNII-37YJW036TP, Anilinoaceticacid, (Phenylamino)acetic Acid; 2-(Phenylamino)acetic Acid; Anilinoacetic Acid; N-(Phenylamino)acetic Acid; NPG; NSC 83567, EINECS 203-070-2, racemic phenylglycine, AM81798, acetic acid, anilino-, A1JJC, N-Phenylglycine, 97%, FT-0695168, Epitope ID:122700, SCHEMBL41828, N-PHENYLGLYCINE [MI], SCHEMBL3117243, SCHEMBL4269014, SCHEMBL6756218, CHEMBL3306206, SCHEMBL16294303, SCHEMBL25383632, ALBB-000236, N-Phenylglycine; LC-tDDA; CE40, BBL012003, SBB028637, STK397549, AKOS000101581, CS-W016312, NCGC00338448-01, AC-13995, AS-31233, SY011199, N-Phenylglycine, purum, >=97.0% (T), NS00023200, ST50632573, EN300-21411, AB01331192-02, AC-907/25014383, F011837, W-108859, N-|A inverted exclamation mark-Aminophenylacetic acid, Z104496210, AURORA KA-3653;ANILINOACETIC ACID;H-PHENYLGLY-OH;N-PHENYLGLYCIN;N-PHENYL-GLY-OH;N-PHENYLAMINOACETIC ACID;N-ALPHA-AMINOPHENYLACETIC ACID;PH-GLY-OH
N-Phenylglycine is generally described as a white crystalline solid.
Reported melting-point values are approximately 121–128 °C, with the exact value depending on the source and material characteristics.
N-Phenylglycine has a relatively low vapor pressure and is normally handled as a solid rather than a volatile liquid.
N-Phenylglycine is a non-proteinogenic amino-acid derivative.
Unlike naturally occurring glycine, its nitrogen is substituted with a phenyl group.
This structural modification gives it chemical properties that differ significantly from ordinary glycine.
One of the most important historical uses of N-Phenylglycine is as an industrial precursor to indigo dye.
N-Phenylglycines chemistry allows it to undergo transformations that ultimately produce indigo and related indigo colorants.
This connection made N-Phenylglycine an important intermediate in the development of industrial indigo synthesis.
N-Phenylglycine became particularly significant in the synthetic dye industry because indigo is an important blue colorant with extensive historical use in textiles.
Industrial synthesis of indigo reduced dependence on natural sources of the dye.
N-Phenylglycine chemistry played a role in establishing practical synthetic routes to indigo.
N-Phenylglycine can undergo cyclization and oxidative transformations that are relevant to indigo synthesis.
The combination of the phenylamine and carboxylic-acid portions of the molecule provides the structural framework required for subsequent reactions.
Industrial processes have historically exploited this chemistry to obtain indigo-related products.
N-Phenylglycine can be produced through organic synthesis involving aniline-derived intermediates.
One reported preparation involves formation of an amino-nitrile followed by hydrolysis to the corresponding carboxylic acid.
The precise manufacturing route depends on the required purity, scale, economics, and downstream application.
N-Phenylglycine is also relevant to specialty organic synthesis.
N-Phenylglycines carboxylic acid and secondary aromatic amine functionalities provide multiple sites for chemical modification.
Researchers can use these functional groups to prepare a variety of substituted derivatives.
N-Phenylglycine can participate in acid–base reactions because it contains a carboxylic acid group and an amine functionality.
N-Phenylglycines ionization behavior can therefore change depending on the pH of the surrounding medium.
This behavior is important when selecting solvents and purification conditions.
The carboxylic acid group allows N-Phenylglycine to participate in esterification and amide-forming reactions.
These transformations can be used to prepare derivatives with modified solubility, reactivity, or physical properties.
Such chemistry is useful in both research and industrial synthesis.
The secondary aromatic amine can also undergo N-functionalization.
Chemical modification of the nitrogen atom can generate substituted anilinoacetic acid derivatives.
This provides additional routes for producing specialty intermediates.
N-Phenylglycine can be investigated in heterocyclic chemistry because its molecular structure can undergo intramolecular transformations.
Cyclization reactions can generate more complex aromatic and nitrogen-containing structures.
This makes the compound useful as a building block in synthetic chemistry.
N-Phenylglycine can also be used in research involving indigoid compounds.
Chemists can modify reaction conditions and substituents to investigate the preparation of indigo derivatives and related conjugated molecules.
Such research is relevant to dyes, pigments, and functional organic materials.
N-Phenylglycine has relevance to dye and pigment manufacturing because its chemistry is connected with indigo-type colorants.
Indigo and related compounds are characterized by extended conjugated structures that produce intense coloration.
This makes the chemistry of N-Phenylglycine particularly important in historical and specialized colorant synthesis.
N-Phenylglycine can also be investigated in photochemical and materials research.
Indigo-derived molecules possess interesting optical and electronic properties because of their conjugated molecular structures.
N-Phenylglycine can therefore appear as an upstream intermediate in research involving such functional molecules.
N-Phenylglycine is useful in analytical chemistry as a defined organic compound that can be characterized using several instrumental techniques.
N-Phenylglycines molecular structure can be confirmed by spectroscopy and chromatography.
This makes it suitable for research, quality control, and chemical identification.
N-Phenylglycine spectroscopy can be used to characterize N-Phenylglycine.
N-Phenylglycine provides information about the aromatic protons, methylene group, and N–H environment, while ¹³C NMR provides information about the aromatic and carboxylic carbons.
These measurements can be useful for confirming identity and purity.
Infrared spectroscopy can also be used to identify the compound.
Characteristic absorptions associated with the carboxylic acid, N–H functionality, aromatic C–H bonds, and C–N bonding provide useful structural information.
FTIR can therefore be used for rapid identification of the material.
Mass spectrometry provides additional information about its molecular mass and fragmentation behavior.
The molecular ion and characteristic fragments can support identification in analytical samples.
N-Phenylglycine is included in established chemical databases with structural and mass-spectral information.
Chromatographic techniques can be used for purity determination and reaction monitoring.
HPLC is particularly useful when N-Phenylglycine must be separated from related aromatic compounds or synthesis impurities.
Analytical monitoring is important when the compound is produced as an intermediate for further processing.
N-Phenylglycine is also relevant to chemical quality control.
Manufacturers may need to monitor starting materials, reaction intermediates, residual impurities, and final purity.
Consistent analytical testing helps ensure reproducible performance in downstream synthesis.
N-Phenylglycine has been listed as having active commercial chemical activity in regulatory chemical inventories.
N-Phenylglycine is therefore encountered as an industrial and laboratory chemical rather than solely as an academic research compound.
Its commercial importance is closely connected to its role as a chemical intermediate.
N-Phenylglycine can be used in laboratory-scale organic synthesis.
Commercial chemical suppliers commonly provide it for research and laboratory applications.
N-Phenylglycine is generally supplied as a chemical reagent or intermediate rather than as a consumer product.
N-Phenylglycine is also relevant to chemical education and research because its structure demonstrates the behavior of molecules containing both carboxylic-acid and aromatic-amine functionalities.
Its reactions can be used to illustrate functional-group transformations and aromatic chemistry.
This makes it a useful compound for synthetic chemistry studies.
N-Phenylglycine may be encountered in photographic and photochemical research involving aromatic organic compounds.
N-Phenylglycines broader chemical family has been investigated in materials and photochemical applications.
However, its principal historical industrial significance remains its relationship to indigo synthesis.
N-Phenylglycine should not be confused with phenylglycine.
Phenylglycine has the phenyl group attached to the carbon atom of the amino-acid structure, whereas N-Phenylglycine has the phenyl group attached directly to nitrogen.
Although the names are similar, they are structurally different compounds.
N-Phenylglycine should also not be confused with N-methylglycine, or sarcosine.
In N-Phenylglycine, the nitrogen carries a phenyl group, while sarcosine contains a methyl group.
This difference significantly changes their physical and chemical properties.
N-Phenylglycine can act as an allergen, according to chemical database information.
This means that appropriate precautions should be taken during repeated handling, particularly in occupational or laboratory environments.
Direct exposure should be minimized even when the material is handled in relatively small quantities.
Available hazard classifications are not completely consistent across all notifications.
Some classifications identify N-Phenylglycine as harmful if swallowed, irritating to the skin and eyes, and capable of causing respiratory irritation, while another notification does not classify it as hazardous under the applicable criteria.
This variation can result from differences in data, impurities, formulations, or notifier assessments.
N-Phenylglycine is therefore best handled as a laboratory or industrial chemical requiring normal chemical-safety precautions.
Avoiding unnecessary dust formation, using appropriate gloves and eye protection, and maintaining adequate ventilation are sensible measures during handling.
The exact precautions should be based on the Safety Data Sheet for the specific grade being used.
N-Phenylglycine is an aromatic amino-acid derivative and valuable organic synthesis intermediate with the formula C₈H₉NO₂, molecular weight 151.16 g/mol, and CAS No. 103-01-5.
N-Phenylglycines most historically significant application is as a precursor in the industrial synthesis of indigo and related colorants, while its reactive functional groups also make it useful in specialty organic synthesis, analytical chemistry, dye research, and chemical manufacturing.
N-Phenylglycine can be characterized using infrared spectroscopy because its functional groups produce identifiable vibrational signals.
The carboxylic acid group gives characteristic absorption features, while the aromatic ring and C–N bonds provide additional spectral information.
NIST lists both infrared and mass spectral information for the compound, supporting its use in analytical identification.
Mass spectrometry can provide complementary information about the molecular composition of N-Phenylglycine.
N-Phenylglycines molecular mass is approximately 151.16 g/mol, corresponding to the molecular formula C₈H₉NO₂.
The fragmentation pattern can also provide information about the stability and cleavage of different portions of the molecule.
Nuclear magnetic resonance spectroscopy is another useful technique for studying N-Phenylglycine.
The aromatic protons provide signals associated with the phenyl ring, while the methylene group adjacent to nitrogen and the acidic proton provide additional structural information.
NMR analysis can therefore help confirm the identity and chemical environment of the different groups within the molecule.
The compound has a relatively low vapor pressure because it is a crystalline organic solid rather than a volatile liquid.
Reported physical-property data include a density of approximately 1.259 and a calculated boiling point around 359 °C at atmospheric pressure.
These values should be regarded as reference data because measured physical properties can vary with experimental conditions and material purity.
N-Phenylglycine is also chemically interesting because its acid-base behavior can influence its physical properties.
The carboxyl group can lose a proton under basic conditions, while the nitrogen atom can participate in protonation and other interactions.
Consequently, pH can influence its solubility, ionic form and behavior during chemical processing.
N-Phenylglycine can be used as a starting point for preparing derivatives with modified aromatic or nitrogen functionality.
Chemical modification of the phenyl ring can alter electronic properties and reactivity, while modification of the carboxyl group can produce esters, amides and other derivatives.
These possibilities make N-Phenylglycine relevant as a building block for exploratory organic synthesis.
N-Phenylglycines chemistry is also relevant to the broader field of nitrogen-containing aromatic compounds.
The combination of an aromatic amine structure with a carboxylic acid allows researchers to investigate reactions involving both nucleophilic nitrogen and acidic carbonyl functionality.
This makes the compound useful for studying reaction mechanisms and synthetic transformations.
N-Phenylglycine is commercially identified under several names, including anilinoacetic acid and glycine, N-phenyl-.
Its European chemical inventory number is EINECS 203-070-2, while its CAS Registry Number is 103-01-5.
These identifiers are useful for distinguishing the substance from structurally related phenylglycine compounds.
N-Phenylglycine remains present in modern chemical databases and laboratory chemical catalogs.
N-Phenylglycine is available primarily as a research and chemical intermediate rather than as a common consumer chemical.
Commercial safety documentation commonly identifies laboratory chemical use as an intended application and advises against food, pharmaceutical, pesticide or biocidal use for that particular product.
The safety information associated with N-Phenylglycine should be interpreted carefully because classifications can differ between regulatory or supplier datasets.
Some available hazard information identifies potential harmful effects if swallowed and possible skin, eye and respiratory irritation, while one supplier SDS has classified a specific product as not hazardous under the cited OSHA standard.
Therefore, handling practices should be based on the current SDS for the exact grade and supplier rather than assuming that every N-Phenylglycine product carries an identical classification.
Melting point: 121-123 °C (lit.)
Boiling point: 273.17 °C (rough estimate)
Density: 1.2023 (rough estimate)
Refractive index: 1.5810 (estimate)
Storage temp.: Store at room temperature
Solubility: Sparingly soluble in DMSO; slightly soluble in methanol
Form: Fine powder
pKa: 1.83, 4.39 (at 25 °C)
Color: Ochre to yellow-brown
Water solubility: Moderately soluble
Merck: 14,7292
BRN: 509838
Major application: Peptide synthesis
InChI: InChI=1S/C8H9NO2/c10-8(11)6-9-7-4-2-1-3-5-7/h1-5,9H,6H2,(H,10,11)
InChIKey: NPKSPKHJBVJUKB-UHFFFAOYSA-N
SMILES: OC(=O)CNc1ccccc1
N-Phenylglycine is an organic aromatic amine and glycine derivative with the molecular formula C₈H₉NO₂ and a molecular weight of approximately 151.16 g/mol.
It is also known as 2-anilinoacetic acid, anilinoacetic acid, and glycine, N-phenyl-.
Its CAS Registry Number is 103-01-5, while its EINECS number is 203-070-2.
A glycine carrying an N-phenyl substituent.
N-Phenylglycine is an aromatic amino-acid derivative containing a phenyl group attached to the nitrogen atom of glycine.
Its molecular formula is C₈H₉NO₂ and its molecular weight is approximately 151.16 g/mol.
N-Phenylglycine is registered under CAS No. 103-01-5 and is also known as anilinoacetic acid or glycine, N-phenyl-.
The molecule contains a benzene ring connected through an amino nitrogen to a methylene group and a carboxylic acid group.
This structure gives N-Phenylglycine both aromatic and carboxylic-acid characteristics, allowing it to participate in a range of organic transformations.
N-Phenylglycines structural representation is commonly written as C₆H₅NHCH₂CO₂H.
N-Phenylglycine is classified as a non-proteinogenic amino acid because it is structurally related to amino acids but is not one of the standard amino acids incorporated into proteins.
N-Phenylglycine can be regarded as a substituted glycine derivative in which the hydrogen attached to the amino nitrogen has been replaced by a phenyl group.
This structural modification gives the compound chemical properties that differ considerably from those of ordinary glycine.
N-Phenylglycine is generally encountered as a white or pale-colored crystalline solid or fine powder.
Reported melting-point values are around 121–128 °C depending on the source and measurement conditions.
Its appearance and melting behavior make melting-point analysis useful for identification and quality control.
N-Phenylglycine contains both acidic and basic functional characteristics within the same molecule.
The carboxyl group can participate in acid-base reactions, while the nitrogen atom can interact with acids and other electrophilic or reactive species.
Under alkaline conditions, the carboxylic acid can form water-soluble salts, which is useful in chemical processing and purification.
One of the most important historical characteristics of N-Phenylglycine is its connection with synthetic indigo production.
The compound became particularly important because it can be converted through cyclization and subsequent oxidation chemistry into indoxyl and ultimately indigo.
This chemistry played an important role in the development of industrially produced indigo dyes.
The transformation of N-Phenylglycine into indigo is associated with the Heumann and Heumann–Pfleger synthetic routes.
Under strongly alkaline and heated conditions, N-Phenylglycine can undergo intramolecular cyclization to form indoxyl-related intermediates.
Oxidation and coupling of indoxyl molecules then produces the characteristic indigo structure.
The industrial importance of this chemistry increased because synthetic indigo offered a more controllable alternative to obtaining the dye from natural plant sources.
The development of synthetic routes eventually transformed indigo production and contributed to the decline of large-scale natural indigo cultivation.
N-Phenylglycine was one of the important intermediates associated with this transition.
Several synthetic approaches have historically been used to obtain N-Phenylglycine.
One important route involves aniline, formaldehyde and hydrogen cyanide to produce an N-phenylglycine nitrile intermediate, which is subsequently hydrolyzed to the corresponding carboxylic acid.
This chemistry is related to the Strecker-type synthesis used in historical indigo manufacturing.
Another historically important approach involves the reaction of aniline with chloroacetic acid.
The reaction introduces the glycine-derived side chain onto the nitrogen atom of aniline, producing N-Phenylglycine.
This intermediate could then be subjected to strongly basic conditions for further transformation toward indoxyl and indigo.
N-Phenylglycine is also interesting from an analytical chemistry perspective because its molecular structure can be investigated using several spectroscopic techniques.
Infrared spectroscopy can provide information about its carboxylic acid and aromatic functional groups, while nuclear magnetic resonance can characterize the aromatic and methylene environments.
Mass spectrometry can additionally be used to confirm its molecular identity and fragmentation behavior.
N-Phenylglycine can also participate in ordinary organic synthesis as a functionalized aromatic amino-acid building block.
The presence of the carboxylic acid and secondary amine provides opportunities for salt formation, derivatization and coupling reactions.
For this reason, the compound can be relevant to laboratory-scale synthesis and research involving nitrogen-containing organic molecules.
Its chemical structure also makes N-Phenylglycine relevant to research involving substituted amino-acid derivatives.
Researchers can modify either the aromatic portion or the functional groups surrounding the nitrogen and carboxyl moieties to investigate changes in reactivity and molecular properties.
Such derivatives can be useful for studying reaction mechanisms and structure-property relationships.
N-Phenylglycine has also been reported in applications involving biochemical and analytical research.
Its similarity to amino-acid structures allows it to serve as a useful model compound when investigating reactions involving amino groups and carboxylic acids.
It has additionally been described in connection with analytical procedures such as colorimetric determination of copper.
N-Phenylglycine has measurable solubility in polar solvents, although its exact solubility depends strongly on temperature, pH and solvent composition.
Its carboxylic acid functionality allows its solubility behavior to change considerably when the compound is converted into an alkaline salt.
This acid-base behavior can be useful when separating, purifying or transferring the material between different chemical phases.
N-Phenylglycine is not simply important because of its historical connection with indigo.
Its combination of an aromatic ring, secondary amino group and carboxylic acid makes it a chemically versatile intermediate for laboratory investigations and synthetic chemistry.
This combination also explains why the compound continues to appear in chemical databases, research literature and commercial chemical catalogs.
N-Phenylglycine's role in indigo chemistry remains one of its most distinctive industrial characteristics.
Modern discussions of synthetic indigo continue to identify N-Phenylglycine among the important historical precursors used to develop efficient chemical routes to indigo.
Indigo itself remains a major textile colorant, particularly because of its long-standing association with denim coloration.
From an industrial chemistry perspective, N-Phenylglycine demonstrates how a relatively small organic molecule can serve as an important intermediate in a much larger manufacturing process.
Its transformation into cyclic intermediates illustrates the importance of condensation, cyclization and oxidation reactions in dye chemistry.
The historical development of these reactions also represents an important stage in the evolution of modern synthetic organic manufacturing.
N-Phenylglycine should therefore be viewed as both an organic synthesis intermediate and a historically significant dye precursor.
Its defined molecular structure, relatively low molecular weight and multiple reactive functional groups make it suitable for controlled chemical transformations.
These characteristics continue to support its use in chemical research, analytical work and specialized synthesis.
N-Phenylglycine is particularly notable because its chemistry connects relatively simple aromatic compounds with the formation of complex heterocyclic structures.
The molecule contains the structural features needed for intramolecular cyclization under strongly alkaline conditions.
This ability is the fundamental reason for its historical importance in the synthesis of indoxyl and indigo.
The nitrogen atom in N-Phenylglycine directly connects the phenyl ring with the glycine-derived carbon chain.
N-Phenylglycine arrangement is different from phenylglycine, where the phenyl group is attached to the carbon atom rather than the nitrogen atom.
The distinction is important because the two compounds have different structures, reaction pathways and chemical behavior.
The carboxylic acid group provides an important reactive site within the molecule.
Under alkaline conditions, this group can be converted into a carboxylate salt, and the resulting salt can behave differently from the free acid.
Historically, alkali-metal salts of N-Phenylglycine were particularly important in the chemistry used for indigo manufacture.
The aromatic ring also contributes significantly to the reactivity of N-Phenylglycine.
During the historical Heumann-type process, the carbon atom of the glycine-derived carboxyl group becomes involved in ring formation with the aromatic portion of the molecule.
This produces an indoxyl-related cyclic structure after suitable alkaline treatment.
The conversion of N-Phenylglycine into indoxyl is an example of a base-promoted cyclization reaction.
Strong alkaline conditions promote the rearrangement and ring-closing chemistry required to construct the fused heterocyclic system.
Indoxyl can subsequently undergo oxidation and coupling reactions that produce indigo.
Uses:
N-Phenylglycine is a derivative of Glycine (G615990).
N-Phenylglycine is also sometimes coupled with Glycidyl methacrylate to create a surface active comonomer that promotes adhesive bonding of materials to hard tooth tissues.
N-Phenylglycine is best known as an important intermediate in the chemical synthesis of indigo.
Its conversion into indoxyl followed by oxidation provides a route to the characteristic indigo molecule used as a textile colorant.
This historical application remains the most distinctive industrial use associated with N-Phenylglycine.
N-Phenylglycine was particularly important in the Heumann and Pfleger methods developed for industrial indigo production.
In these processes, the compound is subjected to strongly alkaline conditions to produce an indoxyl intermediate, which can then be oxidized to indigo.
The development of these processes contributed significantly to the transition from natural indigo production to large-scale synthetic dye manufacturing.
One of its major applications is therefore in dye and pigment chemistry.
The indigo produced through N-Phenylglycine-based chemistry has been historically important for coloration of textiles, particularly cotton fabrics.
Synthetic indigo remains strongly associated with denim manufacturing and blue coloration in the textile industry.
N-Phenylglycine can also be regarded as a specialized organic synthesis intermediate.
Its secondary amine and carboxylic acid functionalities provide sites for chemical transformation, allowing researchers to prepare structurally related compounds.
This makes N-Phenylglycine useful when developing synthetic routes involving aromatic nitrogen-containing molecules.
N-Phenylglycine has applications in laboratory-scale organic chemistry research.
It can be used as a starting material or model compound for investigating reactions involving aromatic amines, carboxylic acids and amino-acid derivatives.
Its well-defined structure also makes it convenient for studying reaction mechanisms and transformation pathways.
Another application is in research concerning indole and indole-related chemistry.
The transformation of N-Phenylglycine into indoxyl provides a useful example of how an acyclic aromatic compound can be converted into a heterocyclic structure.
Consequently, N-Phenylglycine can be encountered in studies dealing with the synthesis and chemistry of indole derivatives.
N-Phenylglycine is also used as a research model in physical organic chemistry.
Its phenyl-substituted nitrogen system can stabilize certain radical intermediates, making the compound useful for investigating photochemical and oxidation processes.
Studies have specifically examined N-Phenylglycine as a model compound for aminium and aminyl radical chemistry.
N-Phenylglycine can therefore contribute to investigations of electron-transfer reactions.
Oxidation of N-Phenylglycine can generate nitrogen-centered radical species whose behavior can be monitored using appropriate analytical techniques.
This provides researchers with a relatively accessible molecular system for studying radical formation and subsequent reactions.
N-Phenylglycine is also relevant to analytical chemistry research.
Its defined molecular structure and known molecular weight make it suitable for identification by techniques such as mass spectrometry, infrared spectroscopy and nuclear magnetic resonance spectroscopy.
Reference spectral information for the compound is available for both infrared and electron-ionization mass spectrometric analysis.
N-Phenylglycine can be used in laboratory investigations where an aromatic amino-acid derivative is required.
Researchers can examine its acid-base behavior, solubility, derivatization reactions and interactions with other chemical species.
These properties make it useful as a controlled model substance in experimental organic chemistry.
N-Phenylglycine can also serve as a starting material for the preparation of derivatives.
The carboxylic acid group can be transformed into different functional groups, while the aromatic ring can be modified through suitable synthetic reactions.
Such modifications allow chemists to investigate how structural changes influence chemical reactivity and physical properties.
N-Phenylglycines carboxylic acid functionality also makes N-Phenylglycine useful in studies involving salt formation and acid-base chemistry.
Conversion of the carboxylic acid into a corresponding salt can alter solubility and processing characteristics.
This behavior can be exploited during laboratory purification and chemical separation procedures.
N-Phenylglycine has been investigated in connection with adhesive chemistry as well.
Research has examined the compound as a functional component in dentin-bonding systems, where its interaction with dental substrates can contribute to adhesion.
This represents a specialized research application rather than the primary industrial use of the substance.
N-Phenylglycine has also been described as a pharmaceutical intermediate in some commercial chemical literature.
Its molecular structure provides a useful starting point for preparing more complex nitrogen-containing organic molecules.
However, claims concerning specific pharmaceutical products should be distinguished from the well-established historical use of N-Phenylglycine as an indigo precursor.
N-Phenylglycine can have relevance in agrochemical synthesis because aromatic amino-acid derivatives can serve as intermediates for more complex functional molecules.
Its reactive nitrogen and carboxyl groups provide opportunities for further chemical modification.
Commercial descriptions have therefore included agrochemical-related synthesis among potential applications, although the exact downstream products depend on the manufacturing route.
N-Phenylglycine can also be used in the preparation and investigation of specialty organic chemicals.
Its relatively simple molecular structure allows it to function as a convenient precursor when additional functional groups need to be introduced.
This type of application is particularly relevant to laboratory and small-scale synthetic chemistry.
Another important use is as a reference or research substance in chemical analysis.
N-Phenylglycine has clearly defined identifiers, including CAS No. 103-01-5, molecular formula C₈H₉NO₂ and molecular weight approximately 151.16 g/mol.
These characteristics allow laboratories to identify and distinguish it from structurally related compounds such as phenylglycine.
N-Phenylglycine can also be used for educational demonstrations of organic reaction chemistry.
Its historical conversion to indigo provides an instructive example of condensation, cyclization, heterocycle formation and oxidation.
The broader chemistry of indigo synthesis is therefore useful for demonstrating how industrial organic synthesis evolved from laboratory-scale reactions.
In chemical manufacturing, N-Phenylglycine can function as a precursor rather than as the final commercial product.
This means that its value is often determined by how efficiently it can be converted into another desired compound.
Its role in the historical production of indigo is a clear example of this type of intermediate-based industrial chemistry.
N-Phenylglycine is also available commercially as a laboratory chemical.
Supplier documentation identifies laboratory chemical use as an intended application and specifically distinguishes this use from food, drug, pesticide and biocidal applications for the referenced product.
This indicates that modern commercial availability is strongly associated with research and chemical synthesis rather than direct consumer use.
N-Phenylglycine is its role as a precursor in synthetic indigo chemistry.
Additional uses include organic synthesis, dye-related research, analytical chemistry, radical and photochemical studies, specialized adhesive research and preparation of other functionalized organic compounds.
Its combination of an aromatic ring, secondary amine and carboxylic acid gives N-Phenylglycine sufficient chemical versatility to remain useful in both industrially relevant chemistry and laboratory research.
N-Phenylglycine has an important role in the preparation of indoxyl, which is the immediate precursor used in several synthetic routes to indigo.
The conversion involves cyclization of N-Phenylglycine under strongly alkaline conditions followed by oxidation of the resulting indoxyl.
This chemistry is one of the main reasons N-Phenylglycine has remained an important compound in the history of industrial dye production.
N-Phenylglycine has therefore been used as an intermediate in large-scale synthetic dye manufacturing.
Its conversion to indigo provided the chemical industry with a route that did not depend on extracting the dye from indigo-producing plants.
Synthetic production subsequently became the dominant approach for supplying indigo for industrial applications.
N-Phenylglycine is particularly associated with the Heumann–Pfleger process for indigo production.
In this process, N-Phenylglycine is converted under alkaline fusion conditions into indoxyl, which is subsequently oxidized to indigo.
The improved process operated at lower temperatures than the original Heumann process and provided better industrial efficiency.
N-Phenylglycine has also been used as an intermediate in the preparation of indigo-related derivatives.
N-substituted glycine compounds and their esters can be transformed into indoxyl derivatives and subsequently into various indigo derivatives.
This chemistry provides a route for modifying the structure and properties of indigo-type compounds.
N-Phenylglycines importance extends into the broader field of color chemistry.
Indigo and related compounds are used as dyes because their conjugated molecular structures produce intense visible coloration.
N-Phenylglycine therefore has indirect importance in textile and specialty colorant chemistry through its conversion into these colored products.
The textile industry represents the most commercially significant downstream application associated with N-Phenylglycine chemistry.
Synthetic indigo produced through related chemical routes is extensively used for dyeing denim and other textile materials.
The characteristic blue coloration of denim is one of the best-known industrial applications connected with this chemistry.
N-Phenylglycine can also be relevant to the preparation of specialty indigo colorants.
Structural modifications of the N-substituted glycine framework can provide access to different indoxyl intermediates and related chromophores.
Such chemistry is useful when researchers need to investigate how molecular structure affects color, stability or dyeing behavior.
N-Phenylglycine has value in synthetic organic chemistry because its functional groups provide several possible reaction sites.
The carboxylic acid can be converted into esters, amides and other derivatives, while the nitrogen atom can participate in further chemical transformations.
This versatility allows N-Phenylglycine to function as a building block in the preparation of more structurally complex molecules.
N-Phenylglycine derivatives have been investigated as intermediates for pharmaceutical synthesis.
Patent literature describes N-substituted glycine acids and esters as useful intermediates for preparing pharmaceutical intermediate products.
The same chemistry can also be adapted for the preparation of other nitrogen-containing specialty chemicals.
N-Phenylglycine and related N-arylglycine structures can also be relevant to agrochemical research.
N-substituted glycine acids and esters can serve as synthetic intermediates for certain herbicide-related compounds.
Their usefulness comes from the ability to transform the glycine-derived functional groups into more complex structures during multistep synthesis.
N-Phenylglycine is useful as a research substrate when studying aromatic amine chemistry.
Its secondary amino group can be involved in protonation, oxidation and other reactions that are characteristic of nitrogen-containing organic molecules.
This makes it suitable for laboratory investigations into reaction mechanisms and intermediate formation.
The molecule can also be used in studies of radical chemistry.
Oxidative reactions involving N-Phenylglycine can generate nitrogen-centered intermediates that are useful for investigating electron-transfer and radical reaction pathways.
Such work contributes to a broader understanding of how aromatic amines behave under oxidative conditions.
N-Phenylglycine can serve as a model compound in analytical investigations of amino-acid derivatives.
N-Phenylglycines known molecular formula, molecular weight and characteristic functional groups make it suitable for identification by spectroscopic methods.
Infrared spectroscopy, mass spectrometry and nuclear magnetic resonance can all provide complementary information about the compound.
Safety Profile:
N-Phenylglycine should be handled as a laboratory chemical with appropriate precautions, particularly when the material is present as a powder.
Available hazard notifications identify possible skin irritation, serious eye irritation and respiratory irritation, while one notification also classifies the substance as harmful if swallowed.
The available classifications are not completely consistent between notifications, so the current SDS for the specific product should always be used for workplace handling.
One of the principal potential hazards is irritation following direct contact with the skin.
Repeated or prolonged contact with the solid material may cause redness, discomfort or irritation in susceptible individuals.
Protective gloves and suitable laboratory clothing are therefore recommended when handling N-Phenylglycine.
Contact with the eyes should also be avoided.
Available GHS notifications classify N-Phenylglycine as capable of causing serious eye irritation in a majority of the reported classifications.
Safety glasses or chemical splash goggles provide appropriate protection during weighing, transferring and preparation of solutions.
Dust generated during handling can present an inhalation concern.
Available classifications indicate that N-Phenylglycine may cause respiratory irritation, particularly when airborne particles are inhaled.
Operations that can generate dust should therefore be performed with adequate local ventilation or appropriate respiratory protection where required.
Inhalation exposure is particularly relevant when the material is handled as a fine powder.
Opening containers, weighing the substance or transferring it between vessels can release small particles into the surrounding air.
Avoiding unnecessary dust formation and maintaining good laboratory ventilation can substantially reduce this exposure route.
Ingestion should also be prevented during laboratory handling.
One-third of the available GHS notification reports classify N-Phenylglycine as harmful if swallowed, although the other reported classifications do not include this hazard.
Eating, drinking and smoking should therefore be avoided in areas where the chemical is handled, and hands should be washed thoroughly after use.
Supply Of N-Phenylglycine:
For further information about N-Phenylglycine, including available product grades, technical specifications, application suitability and supply options, please contact Ataman Kimya.
