Ethyl 2-(2-aminophenyl)acetate: Properties & Lab Uses

Ethyl 2-(2-aminophenyl)acetate is a bifunctional aromatic building block featuring both a free primary amine and an ethyl ester group on an ortho-substituted benzene ring, making it a versatile intermediate in pharmaceutical and fine-chemical synthesis.

IUPAC Name

Ethyl 2-(2-aminophenyl)acetate

SKU

E770462

Molecular Formula

C10H13NO2

Molecular Weight

179.22 g/mol

Key Functional Groups

Primary aromatic amine (–NH2) and ethyl ester (–CO2Et)

Primary Application

Pharmaceutical intermediate and heterocyclic scaffold synthesis

Chemical Identity and Structure

Ethyl 2-(2-aminophenyl)acetate (CAS number should be confirmed; see review flags) is an ortho-substituted phenylacetate ester. Its molecular formula is C₁₀H₁₃NO₂, giving a molecular weight of approximately 179.22 g/mol. The compound possesses two reactive functional groups in close spatial proximity: a primary aromatic amine (–NH₂) at the 2-position of the benzene ring and an ethyl ester (–CO₂Et) on the pendant acetic acid moiety. This ortho relationship between the amine and the ester-bearing methylene group creates an intramolecular geometry that facilitates cyclization reactions, a feature exploited extensively in synthetic chemistry.

The compound is typically encountered as a pale yellow to colorless liquid or low-melting solid and should be stored under cool, dry, inert-atmosphere conditions to prevent oxidation of the amine functionality and hydrolysis of the ester. Aladdin Scientific supplies this reagent under SKU E770462.

Synthesis and Reactivity

Ethyl 2-(2-aminophenyl)acetate is commonly prepared by Fischer esterification of 2-(2-aminophenyl)acetic acid (homanilic acid) with ethanol under acid catalysis, or by selective reduction of the nitro group in ethyl 2-(2-nitrophenyl)acetate using catalytic hydrogenation or chemical reductants such as iron/acetic acid or tin(II) chloride. The ester moiety is stable under the mild conditions typically used for nitro reduction, allowing chemoselective access to the free amine product.

The bifunctional nature of the molecule enables a wide range of transformations. The aromatic amine can undergo acylation, sulfonylation, reductive amination, diazotization, and condensation reactions. Concurrently, the ethyl ester can participate in Claisen-type condensations, aminolysis (to form amides), or hydrolysis. The proximity of the two groups particularly favors intramolecular lactam or dihydroisoquinolinone formation under appropriate conditions.

Applications in Pharmaceutical and Fine-Chemical Research

The primary value of Ethyl 2-(2-aminophenyl)acetate lies in its role as a building block for nitrogen-containing heterocyclic compounds. Researchers use it as a precursor to benzodiazepine-related scaffolds, oxindoles, isatins, dihydroisoquinolinones, and benzazepine frameworks—structural motifs that appear frequently in CNS-active drugs, kinase inhibitors, and antimicrobial agents. The amine group provides a handle for amide-bond formation with activated carboxylic acids, enabling the construction of peptidomimetic or macrocyclic architectures.

In medicinal chemistry campaigns, the compound serves as a versatile aniline surrogate for structure–activity relationship (SAR) studies. Its ethyl ester functionality can be hydrolyzed to the corresponding carboxylic acid for further elaboration or used directly in condensation reactions to generate cyclic imides and diketopiperazines. Industrial fine-chemical manufacturers also employ it as an intermediate in the preparation of agrochemicals and specialty dyes.

Handling, Safety, and Storage

As with all primary aromatic amines, Ethyl 2-(2-aminophenyl)acetate should be handled with appropriate precautions. Primary aromatic amines are a recognized chemical class of concern due to potential mutagenic and sensitizing properties; however, specific hazard data for this compound should be verified from the current Safety Data Sheet (SDS) supplied by Aladdin Scientific. Users should consult the SDS for GHS classification, first-aid measures, and disposal guidance before use.

Recommended handling practices include use of nitrile gloves, safety eyewear, and a laboratory fume hood. The compound should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C or as specified on the product label, away from oxidizing agents, strong acids, and strong bases. Prolonged exposure to light and air may cause discoloration of the amine functionality.

Frequently asked questions

What is Ethyl 2-(2-aminophenyl)acetate used for in organic synthesis?

Ethyl 2-(2-aminophenyl)acetate is widely used as a bifunctional building block in the synthesis of nitrogen-containing heterocycles, including benzodiazepines, dihydroisoquinolinones, oxindoles, and related pharmaceutical scaffolds. Its free amine and ethyl ester groups enable diverse condensation, cyclization, and amide-forming reactions. It is also used in SAR studies and as a precursor to agrochemical intermediates.

How should Ethyl 2-(2-aminophenyl)acetate be stored to maintain stability?

The compound should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C, away from light, moisture, oxidizing agents, and strong acids or bases. These precautions prevent oxidation of the aromatic amine and hydrolysis of the ethyl ester. Always consult the current Aladdin Scientific SDS for definitive storage conditions.

What is the molecular formula and molecular weight of Ethyl 2-(2-aminophenyl)acetate?

Ethyl 2-(2-aminophenyl)acetate has the molecular formula C10H13NO2 and a molecular weight of approximately 179.22 g/mol. The structure features a benzene ring with an ortho amino substituent and a pendant ethyl ester group via a methylene linker.

Is Ethyl 2-(2-aminophenyl)acetate the same as Ethyl 2-(2-aminophenyl)acetate supplied by other vendors?

The chemical identity (molecular formula, molecular weight, and structure) is the same regardless of supplier; however, purity grade, specification, and quality-control documentation may differ between vendors. Aladdin Scientific supplies this compound under SKU E770462. Researchers should compare Certificates of Analysis and purity specifications when selecting a source for critical applications.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for amine and ester reactivity.)
2. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for heterocycle synthesis and functional group transformations.)
3. Aladdin Scientific. Product Page: Ethyl 2-(2-aminophenyl)acetate, SKU E770462. (Supplier product documentation.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.