2-(p-Tolylethynyl)aniline: Properties, Uses & FAQs

2-(p-Tolylethynyl)aniline is an internal alkyne-bearing aromatic amine that serves as a versatile building block for the synthesis of nitrogen-containing heterocyclic compounds and functional organic materials.

Product Name

2-(p-Tolylethynyl)aniline

SKU / Catalog Number

A727905

Molecular Formula

C15H13N

Molecular Weight

207.27 g/mol

Functional Groups

Primary aromatic amine (–NH2) and internal alkyne (–C≡C–)

Typical Application

Heterocycle synthesis, cyclization reactions, and organic materials research

Storage Recommendation

Store in a cool, dry, well-ventilated area away from light and moisture

What Is 2-(p-Tolylethynyl)aniline?

2-(p-Tolylethynyl)aniline (CAS not confirmed in source material; see review flags) is an aromatic compound featuring two key functional groups: a primary amine (–NH₂) attached to a benzene ring and an internal alkyne (–C≡C–) linking that ring to a para-methylphenyl (p-tolyl) group. Its molecular formula is C₁₅H₁₃N with a molecular weight of approximately 207.27 g/mol.

The orthogonal reactivity of the amine and alkyne moieties in a single molecule makes this compound particularly attractive as a bifunctional building block. It is catalogued by Aladdin Scientific under SKU A727905 and is intended for research use in organic synthesis and materials science.

Applications in Organic Synthesis

The combination of an ortho-amino group and a tethered internal alkyne positions 2-(p-Tolylethynyl)aniline as a substrate for a range of cyclization strategies. In transition-metal-catalyzed reactions, the amine and alkyne can cooperate to form five- or six-membered nitrogen heterocycles such as indoles, isoquinolines, and related scaffolds, which are prevalent in pharmaceuticals and agrochemicals.

Beyond heterocycle formation, the compound can participate in click-chemistry-inspired transformations, Sonogashira-type couplings (using the amine as a directing or protecting handle), and annulation sequences. Researchers in organic electronics have also employed structurally analogous ortho-alkynylanilines as precursors to conjugated materials.

Note: Specific reaction yields, conditions, and literature references for this exact compound have not been verified from the supplied source material and should be confirmed before use in publications.

Handling, Safety, and Storage

As with most primary aromatic amines, 2-(p-Tolylethynyl)aniline should be handled with appropriate personal protective equipment including nitrile gloves, safety goggles, and a laboratory coat. Operations that may generate dust or aerosols should be conducted in a fume hood.

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, away from direct light, moisture, heat sources, and incompatible oxidizing agents. Verify the current Safety Data Sheet (SDS) available from Aladdin Scientific for precise hazard classifications, GHS pictograms, and first-aid measures before handling.

Specific hazard classifications (e.g., GHS categories, LD₅₀ values) for this compound are not confirmed in the supplied source material and should be obtained from the official SDS.

Purity, Specification, and Quality

Aladdin Scientific supplies 2-(p-Tolylethynyl)aniline under SKU A727905. Researchers requiring high purity material for sensitive applications such as catalysis studies or analytical reference work should request the current certificate of analysis (CoA) at the time of ordering to confirm lot-specific purity, appearance, and analytical data.

Standard characterization methods for this class of compound typically include high-performance liquid chromatography (HPLC) for purity assessment, nuclear magnetic resonance (NMR) spectroscopy for structural confirmation, and mass spectrometry (MS) for molecular weight verification. Contact Aladdin Scientific technical support for lot-specific CoA documents.

Exact purity grade and specification values are not provided in the source material; these should be verified directly with Aladdin Scientific.

Ordering and Customer Support

2-(p-Tolylethynyl)aniline is available from Aladdin Scientific with catalog number A727905. To place an order, visit the Aladdin Scientific website, search by SKU or product name, select your required quantity, and proceed through the standard checkout process. Bulk or custom quantities may be available upon request.

For technical questions about the compound, requests for Safety Data Sheets or Certificates of Analysis, or assistance with order status and returns, please contact Aladdin Scientific customer service. Refer to the site's shipping, payment, and return policies for full terms applicable to your region.

Frequently asked questions

What is the molecular formula and molecular weight of 2-(p-Tolylethynyl)aniline?

2-(p-Tolylethynyl)aniline has the molecular formula C15H13N and a molecular weight of approximately 207.27 g/mol. It contains a primary aromatic amine and an internal alkyne as the key functional groups.

What are the typical synthetic applications of 2-(p-Tolylethynyl)aniline?

This compound is primarily used as a bifunctional building block in the synthesis of nitrogen-containing heterocycles such as indoles and isoquinolines via transition-metal-catalyzed cyclization. It may also find use in conjugated organic material synthesis and annulation chemistry. Specific literature examples should be confirmed independently before use.

How should 2-(p-Tolylethynyl)aniline be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location away from light, moisture, and heat sources. As with other aromatic amines, exposure to air and light over prolonged periods may cause discoloration or degradation. Always consult the current SDS from Aladdin Scientific for authoritative storage guidance.

What catalog number should I use to order 2-(p-Tolylethynyl)aniline from Aladdin Scientific?

You should use catalog number A727905 to order 2-(p-Tolylethynyl)aniline from Aladdin Scientific. You can search this SKU directly on the Aladdin Scientific website to view available pack sizes and pricing.

Is a Certificate of Analysis (CoA) available for 2-(p-Tolylethynyl)aniline?

Yes, Aladdin Scientific typically provides lot-specific Certificates of Analysis upon request. When placing your order for SKU A727905, you may request the CoA through the website or by contacting Aladdin Scientific customer support to confirm purity and analytical data for your specific lot.

References

1. Aladdin Scientific product listing: 2-(p-Tolylethynyl)aniline, SKU A727905.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed. Wiley-Interscience, 1992. (General reference for aromatic amine and alkyne reactivity.)

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