N,N-Diallylaniline: Properties, Uses & FAQs

N,N-Diallylaniline is a tertiary amine featuring a phenyl group and two allyl substituents on nitrogen, making it a versatile building block for organic synthesis, polymer chemistry, and functional material research.

Chemical Name

N,N-Diallylaniline

Molecular Formula

C₁₂H₁₅N

Functional Groups

Tertiary amine; two terminal alkene (allyl) groups; phenyl ring

Aladdin SKU

N770914

Compound Class

Aromatic tertiary amine / diallylamino compound

Primary Research Uses

Organic synthesis intermediate, monomer for polymerization, ligand precursor

What Is N,N-Diallylaniline?

N,N-Diallylaniline is an aromatic tertiary amine in which the nitrogen atom bears one phenyl group and two allyl (prop-2-en-1-yl) groups. The combination of a nucleophilic amine center with two reactive terminal double bonds makes this compound a bifunctional building block of broad utility in preparative organic chemistry.

The compound belongs to the class of diallylamine derivatives, a family well-known in polymer science because the two vinyl-type side chains can participate in radical or metal-catalyzed cyclopolymerization reactions, yielding nitrogen-containing cyclic repeat units. The phenyl substituent modifies the electron density on nitrogen and imparts additional structural rigidity compared with purely aliphatic diallylamine analogs.

Key Physicochemical Properties

N,N-Diallylaniline is a liquid at ambient temperature with a characteristic amine odor. Its molecular formula is C₁₂H₁₅N and its molecular weight is approximately 173.25 g/mol. The compound is miscible with common organic solvents such as ethanol, diethyl ether, dichloromethane, and toluene, but has limited water solubility due to its largely hydrophobic framework.

The terminal alkene groups are susceptible to radical addition, hydrogenation, hydroboration, and transition-metal-catalyzed reactions (e.g., hydroformylation, metathesis). The amine nitrogen can act as a ligand toward Lewis-acidic metals or be quaternized with alkyl halides. These combined reactivities define the compound's utility across multiple synthetic strategies.

Note: Specific physical constants (boiling point, density, refractive index) should be verified against the current Aladdin Certificate of Analysis for lot-specific data.

Research and Industrial Applications

Polymer Chemistry: N,N-Diallylaniline serves as a monomer in cyclopolymerization reactions. Diallylammonium and diallylamine monomers are established precursors to polycationic and functional polymers used in water treatment, ion-exchange membranes, and specialty coatings. The phenyl group in N,N-diallylaniline can be exploited to tune solubility, thermal stability, and optical properties of the resulting polymer.

Organic Synthesis: The compound is used as an amine building block for constructing more complex molecular architectures, including heterocyclic compounds accessible via intramolecular cyclization of the allyl arms. It can also serve as a directing or protecting group strategy owing to the N-allyl moieties, which are removable under palladium-catalyzed deallylation conditions.

Coordination Chemistry and Catalysis: The nitrogen lone pair makes N,N-diallylaniline a potential hemilabile ligand precursor, where the allyl double bonds provide additional coordination sites for transition metals, potentially enabling catalyst development or mechanistic studies.

Material Science: Incorporation into cross-linked networks via the two polymerizable double bonds allows preparation of thermoset resins or hydrogel scaffolds with embedded amine functionality for pH-responsive or metal-chelating behavior.

Handling, Storage, and Safety Considerations

As with most tertiary amines, N,N-Diallylaniline should be handled in a well-ventilated fume hood. Personal protective equipment including nitrile gloves, safety goggles, and a lab coat is recommended. Avoid inhalation of vapors and contact with skin or eyes.

Store the compound in a tightly sealed container under inert atmosphere (nitrogen or argon) in a cool, dry location away from oxidizers, strong acids, and ignition sources. The terminal alkene groups can undergo slow autopolymerization or oxidation on prolonged exposure to light, air, or elevated temperatures; addition of a radical inhibitor may be warranted for long-term storage.

Regulatory note: Consult the current Safety Data Sheet (SDS) available from Aladdin Scientific for precise hazard classifications, GHS pictograms, first-aid measures, and disposal requirements before use. Specific hazard data should be taken from the official SDS rather than this article.

Ordering and Specifications for SKU N770914

Aladdin Scientific supplies N,N-Diallylaniline under SKU N770914. Researchers should request the current Certificate of Analysis (CoA) to confirm lot-specific purity, water content, and spectral data (NMR, GC) prior to use in sensitive applications.

For bulk quantities, custom packaging, or specific purity grades, contact Aladdin's technical sales team. Volume pricing and institutional account options are available. When placing an order, ensure the correct SKU is selected to avoid confusion with structurally related analogs (e.g., N,N-diallylamine or N-allylaniline).

Standard quality checks performed by Aladdin may include GC purity determination and NMR structure confirmation. Refer to the product page on the Aladdin website or contact customer service for current stock availability and lead times.

Frequently asked questions

What is N,N-Diallylaniline used for in research?

N,N-Diallylaniline is primarily used as an organic synthesis intermediate and monomer in polymer chemistry. Its two reactive allyl groups enable participation in radical cyclopolymerization, olefin metathesis, and palladium-catalyzed reactions, while the amine nitrogen serves as a nucleophile, ligand donor, or site for quaternization. It is also explored in material science for constructing nitrogen-functionalized cross-linked networks.

How should N,N-Diallylaniline be stored to maintain stability?

Store N,N-Diallylaniline in a tightly sealed container under an inert atmosphere (nitrogen or argon) in a cool, dark, and dry location. Because the terminal alkene groups are susceptible to autopolymerization and oxidative degradation, prolonged exposure to air, light, or heat should be avoided. Addition of a radical inhibitor is advisable for long-term storage, and the compound should be kept away from strong oxidizers and acids.

What is the difference between N,N-Diallylaniline and N,N-Diallylamine?

N,N-Diallylamine (H-N(CH₂CH=CH₂)₂) is a secondary amine with two allyl groups and a hydrogen on nitrogen, whereas N,N-Diallylaniline has a phenyl group replacing that hydrogen, making it a tertiary amine. This structural difference significantly affects basicity (the phenyl group lowers nitrogen nucleophilicity through resonance delocalization), reactivity toward electrophiles, and the physical properties of any derived polymers or heterocycles.

Is N,N-Diallylaniline compatible with palladium-catalyzed cross-coupling reactions?

N,N-Diallylaniline can interact with palladium catalysts through both its nitrogen lone pair and its terminal alkene groups, which may act as ligands or substrates. The allyl units are amenable to Pd-catalyzed allylic functionalization (Tsuji–Trost-type chemistry) and deallylation. Researchers should evaluate potential catalyst poisoning by the amine nitrogen when using it in Pd-catalyzed cross-coupling sequences and may need to optimize ligand choice or reaction conditions accordingly.

How do I confirm the purity of N,N-Diallylaniline (SKU N770914) from Aladdin?

Request the Certificate of Analysis (CoA) for your specific lot from Aladdin Scientific, which typically includes GC purity data and NMR structure confirmation. For critical applications, you may independently verify purity by GC-FID, ¹H NMR, or Karl Fischer titration for water content. Contact Aladdin customer service or visit the product page online to download the CoA or request additional quality documentation.

References

1. Wandrey, C.; Hernández-Barajas, J.; Hunkeler, D. Diallyldimethylammonium Chloride and its Polymers. Advances in Polymer Science, 1999, 145, 123–183. [General reference on diallylammonium cyclopolymerization; relevance to diallylaniline analogs inferred.]
2. Aladdin Scientific Product Page: N,N-Diallylaniline, SKU N770914. Aladdin Scientific Corp. [Accessed via internal product database.]
3. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. [General textbook reference for amine reactivity and allyl chemistry.]

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