4-tert-Butyl-N-phenylaniline: Properties, Uses & FAQs
4-tert-Butyl-N-phenylaniline: Properties, Uses & FAQs
4-tert-Butyl-N-phenylaniline is a secondary diarylamine building block featuring a sterically demanding tert-butyl substituent that enhances solubility and thermal stability, making it a versatile intermediate in organic synthesis and materials research.
- CAS Number
- 3440-02-6
- Molecular Formula
- C₁₆H₁₉N
- Molecular Weight
- 225.33 g/mol
- Compound Class
- Secondary diarylamine
- Key Structural Feature
- para-tert-butyl group on one phenyl ring; N–H secondary amine
- Aladdin SKU
- D303740
What Is 4-tert-Butyl-N-phenylaniline?
4-tert-Butyl-N-phenylaniline (CAS 3440-02-6) is a secondary diarylamine in which a diphenylamine core carries a para-tert-butyl substituent on one of the phenyl rings. The compound has the molecular formula C₁₆H₁₉N and a molecular weight of approximately 225.33 g/mol. The nitrogen atom retains a single N–H proton, classifying it as a secondary amine and enabling further functionalization via N-alkylation, N-arylation, or oxidative coupling reactions.
The bulky tert-butyl group increases steric shielding around the aromatic system, which typically improves solubility in common organic solvents (e.g., dichloromethane, toluene, THF) and can raise the glass-transition temperature of polymeric or small-molecule materials derived from it. These properties are exploited in the design of hole-transport layers for organic light-emitting diodes (OLEDs), organic photovoltaics, and related devices.
Handling, Storage, and Safety
As with most secondary aromatic amines, 4-tert-Butyl-N-phenylaniline should be handled with appropriate personal protective equipment, including nitrile gloves, safety glasses, and a lab coat. Work in a well-ventilated area or fume hood to minimise inhalation exposure to dust or vapour.
The compound is typically stored at room temperature in a tightly sealed container, away from strong oxidising agents, strong acids, and light. Long-term storage under an inert atmosphere (nitrogen or argon) is recommended to prevent slow oxidation of the amine nitrogen. Always consult the current Safety Data Sheet (SDS) supplied with product D303740 for authoritative hazard, first-aid, and disposal information before use.
Research and Synthetic Applications
4-tert-Butyl-N-phenylaniline serves primarily as a synthetic intermediate. Its N–H group participates readily in palladium-catalysed C–N cross-coupling reactions (e.g., Buchwald–Hartwig amination), enabling the construction of triarylamines and more complex nitrogen-containing architectures used in organic semiconductors and dyes.
In materials science, triarylamine motifs derived from this compound are of interest as hole-transport units because of the high-lying HOMO energies characteristic of diarylamines. The tert-butyl group also reduces intermolecular π–π stacking, which can improve thin-film morphology. Additionally, the compound may be used as a stabiliser or antioxidant precursor, as hindered secondary amines are known to scavenge radical species in polymer formulations.
Purity, Grade, and Quality Specifications
Aladdin Scientific offers 4-tert-Butyl-N-phenylaniline (SKU D303740) as a research-grade reagent. Purity is confirmed by standard analytical techniques including GC or HPLC. Buyers should refer to the certificate of analysis (CoA) supplied with each lot for the exact purity figure, melting-point range, and any additional quality parameters relevant to their application.
For applications sensitive to trace metal contamination—such as OLED device fabrication—researchers may wish to request lot-specific ICP-MS data or perform additional purification (e.g., recrystallisation from ethanol or column chromatography) prior to use. Contact Aladdin Scientific technical support for custom purity requirements or bulk quantities.
Ordering and Availability
4-tert-Butyl-N-phenylaniline is listed in the Aladdin Scientific catalogue under SKU D303740. It is available in standard pack sizes suitable for laboratory-scale research. To place an order, search for D303740 on the Aladdin Scientific website or contact your regional sales representative. Bulk and custom quantities may be arranged through the custom synthesis or bulk sales team.
For current pricing, lead times, and stock availability, please visit the product page directly or contact Aladdin Scientific customer service. Export regulations may apply depending on destination country; buyers are responsible for compliance with local import rules.
Frequently asked questions
What is the CAS number for 4-tert-Butyl-N-phenylaniline?
The CAS registry number for 4-tert-Butyl-N-phenylaniline is 3440-02-6. You can use this number to cross-reference the compound in chemical databases such as SciFinder, Reaxys, or PubChem before ordering SKU D303740 from Aladdin Scientific.
How should 4-tert-Butyl-N-phenylaniline be stored to maintain stability?
The compound should be stored in a tightly sealed container at room temperature, protected from light, moisture, and strong oxidising agents. For long-term preservation, storage under an inert atmosphere (nitrogen or argon) is recommended to prevent oxidation of the secondary amine group. Always consult the product SDS for definitive storage guidance.
What are the main research applications of 4-tert-Butyl-N-phenylaniline?
This compound is primarily used as a synthetic intermediate for building triarylamine-based hole-transport materials employed in OLEDs, organic photovoltaics, and related organic electronic devices. It also participates in palladium-catalysed Buchwald–Hartwig amination reactions and may serve as a precursor to hindered amine stabilisers in polymer chemistry.
Is 4-tert-Butyl-N-phenylaniline soluble in common laboratory solvents?
Yes, the presence of the tert-butyl group generally enhances solubility in nonpolar and moderately polar organic solvents such as dichloromethane, toluene, and THF. Exact solubility data should be confirmed experimentally for the specific concentrations and conditions required in your application.
What purity grade is available for D303740, and how is purity verified?
Aladdin Scientific supplies D303740 as a research-grade reagent; purity is verified by GC or HPLC analysis. The exact purity specification for each lot is detailed in the certificate of analysis (CoA) available upon request. Researchers requiring higher purity for sensitive applications should contact Aladdin Scientific technical support for options such as additional lot testing or custom purification.
References
- PubChem Compound Summary for CAS 3440-02-6, 4-tert-Butyl-N-phenylaniline. National Library of Medicine.
- Hartwig, J. F. Palladium-catalysed amination of aryl halides and sulfonates. Pure and Applied Chemistry, 1999.
- Shirota, Y.; Kageyama, H. Charge carrier transporting molecular materials and their applications in devices. Chemical Reviews, 2007.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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