4-Tritylaniline - ≥97% , CAS No.22948-06-7

CAS: 22948-06-7 Cat. No.: T168801 Formula: C₂₅H₂₁N Molecular Weight: 335.44 EC Number: 245-346-5 PubChem CID: 89914

GRADE & PURITY ≥97%

Synonyms

4-Aminotetraphenylmethan | DTXSID8066844 | Triphenylmethyl-containing compound, 19 | 3-Piperidine-4-yl-propionic acid | MFCD00007898 | p-Toluidine, alpha,alpha,alpha-triphenyl- | 4-pyrrolidinocarbonylpiperidine | 4-Aminotetraphenylmethane | Benzenamine,4-

Storage

Room temperature,Argon charged

Shipped In

Normal

Overview

4-Tritylaniline was used in the preparation of:
• 5-tritylisatin
• 2,7-di-tert-butyl-9,9-dimethyl-4,5-bis(4-tritylanilinocarbonyl)-9H-xanthene methanol trisolvate monohydrate
• bis-4,4-[6-chloro-N-(4-tritylphenyl)-[1,3,5]triazine-2,4-diamine]-[2,2-disulfonic acid]-stilbene, novel fluorophore, with potential application as an optical brightener

Specifications

Synonyms

4-Aminotetraphenylmethan | DTXSID8066844 | Triphenylmethyl-containing compound, 19 | 3-Piperidine-4-yl-propionic acid | MFCD00007898 | p-Toluidine, alpha,alpha,alpha-triphenyl- | 4-pyrrolidinocarbonylpiperidine | 4-Aminotetraphenylmethane | Benzenamine,4-

Specifications & Purity

≥97%

Storage

Room temperature,Argon charged

Shipped In

Normal

Purity

≥97%

Names and Identifiers

Pubchem Sid

488186579

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488186579

Canonical Smiles

C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=C(C=C4)N

IUPAC Name

4-tritylaniline

InChIKey

XYHDHXBLSLSXSR-UHFFFAOYSA-N

INCHI

1S/C25H21N/c26-24-18-16-23(17-19-24)25(20-10-4-1-5-11-20,21-12-6-2-7-13-21)22-14-8-3-9-15-22/h1-19H,26H2

Isomeric SMILES

C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=C(C=C4)N

WGK Germany

3

RTECS

CY1220000

PubChem CID

89914

Molecular Weight

335.44

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Aniline and substituted anilines

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Aniline and substituted anilines
• Intermediate Tree Nodes: Not available
• Direct Parent: Aniline and substituted anilines
• Alternative Parents: Primary amines Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aniline or substituted anilines - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 255-257 °C
• Molecular Weight: 335.400 g/mol
• XLogP3: 6.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 335.167 Da
• Monoisotopic Mass: 335.167 Da
• Topological Polar Surface Area: 26.000 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 358.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No tested bioassay or immunoassay protocols are provided for this small-molecule product. Typical handling in synthetic labs involves dissolution in an organic solvent (see Solvent Selection) and use under inert atmosphere as indicated in the Product Data. If used in analytical methods:

• NMR sample prep (general): 10–30 mg in 0.6–0.7 mL of CDCl3 or DMSO-d6; add TMS or residual solvent reference.
• HPLC/LC-MS (general): dissolve to 0.1–1 mg/mL in ACN/MeOH with 0.1% formic acid if positive ESI is desired; ensure complete dissolution and filtration (PTFE syringe filter, 0.2 µm) for analytical runs.

For synthetic protocols specific to your transformation (acylation, cross-coupling, diazotization), refer to the Reaction Conditions section and adapt to your substrate/catalyst system.

Biological Roles

4-Tritylaniline is a synthetic, highly aromatic amine used as a chemical building block and intermediate. It does not have a recognized natural biological role.

• General notes (literature/general):

  • Triarylmethane derivatives are common motifs in dyes and organic electronic materials; some members exhibit interactions with biological macromolecules due to cationic triarylmethyl forms, but such properties are structure-dependent and not generalizable to 4-tritylaniline.
  • The neutral aniline is hydrophobic and is not expected to be appreciably bioavailable in aqueous systems without formulation.

• Research-only notice: As per Product Data, for research use only. No clinical or diagnostic claims are made. If used in bioassays, ensure appropriate solvent vehicles (e.g., DMSO) and confirm lack of assay interference (e.g., absorbance/fluorescence from the aromatic core) in controls.

Buffer Applications

This compound is a non-ionic, water-insoluble aromatic amine and is not used as a buffer component. It lacks acid/base pairs in the physiological pH window that would provide meaningful buffering capacity in water.

• Practical guidance:
  • If handling in aqueous systems (e.g., biological assays), it will require a co-solvent such as DMSO or surfactants; select a buffer independently (e.g., phosphate, HEPES) appropriate to your assay.
  • Refer instead to the Solvent Selection and Reaction & Applications sections for relevant use-cases.

Green Alternatives

This product is a solid building block rather than a solvent. Greener considerations therefore center on the choice of processing solvents and reagents when using 4-tritylaniline.

• Prefer greener solvents when feasible (literature/guidance):

  • Replace DCM/CHCl3 with EtOAc, 2-MeTHF, CPME, or toluene for extractions and acylations.
  • Use 2-MeTHF or CPME in place of THF for moisture-tolerant couplings; both offer improved safety and life-cycle metrics.
  • For polar media, replace DMF/DMAc with propylene carbonate or Cyrene where compatible with the chemistry; assess catalyst solubility.

• Example comparison (general):

  • DCM vs EtOAc: EtOAc has lower toxicity, is bio-based route-enabled, and is readily biodegradable; note lower solvency for very nonpolar solids.
  • THF vs 2-MeTHF: 2-MeTHF forms fewer peroxides and has a higher boiling point, facilitating azeotropic drying; may change reaction rates/selectivity.
  • DMF vs Cyrene/PC: greener alternatives reduce reproductive toxicity concerns but may alter base/catalyst compatibility.

• Reagent choices:

  • For acylations, use acid anhydrides with catalytic DMAP instead of acid chlorides where possible to minimize HCl generation.
  • Avoid stoichiometric strong Lewis acids for trityl functionalization when catalytic, milder protocols (e.g., Brønsted acid catalysis, photoredox) are available.

Conduct small-scale trials to ensure the alternative medium maintains yield and selectivity with this bulky aryl amine.

Pharmaceutical Uses

No pharmacopeial or excipient status is indicated for this item. 4-Tritylaniline is supplied for research use only and is primarily a synthetic intermediate/building block.

• Potential roles in pharmaceutical R&D (literature/general, non-clinical):

  • As a scaffold or starting material in the synthesis of triarylmethane-containing libraries for screening (materials-like properties, high aromatic density).
  • As a bulky aryl amine component for probing SAR related to steric bulk, electronics, or to serve as a protecting/space-filling group in medicinal chemistry routes.

• Formulation note: If evaluated in discovery assays, dissolution typically requires organic co-solvents (DMSO, DMF). Confirm compound compatibility with assay readouts due to strong UV absorbance from the aromatic core.

• Regulatory note: Not an approved drug or excipient. No medical or therapeutic claims are made or implied.

Physical Properties

Item-specific specs are not provided in the Product Data. Values below are literature/general and for reference only (not specifications).

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (Typically a crystalline solid, literature.)
• Melting point: literature reports ~156–160 °C for 4-tritylaniline (source: chemical supplier and handbook data; values vary by source). Not a specification.
• Boiling point: decomposes before boiling under ambient pressure; definitive BP not typically reported (literature). Not a specification.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (qualitative, literature):
  • Insoluble/negligibly soluble in water.
  • Soluble in common organic solvents such as dichloromethane, chloroform, toluene, THF, dioxane; increased solubility in polar aprotic solvents (DMF, NMP).
• LogP: Expected to be high due to four phenyl rings (literature expectation); no numerical value provided.
• pKa: The anilinium conjugate acid typically pKa ~4.5–5.5 (literature range for anilines). Bulky para trityl substituent slightly modulates basicity; no item-specific value.
• UV-Vis: Triarylmethane framework shows strong aromatic absorption in UV; exact cutoff/ε Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable to solids; Not specified for this item.

Always confirm critical parameters experimentally for your specific batch.

Quality & Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• What grade implies (general guidance):
  • If offered in research/technical grade, purity is typically suitable for synthetic applications (building block, ligand precursor) but may contain trace organic/metallic impurities. If HPLC grade or ≥98–99% stated on CoA, the material is appropriate for applications sensitive to trace chromophores or for calibration work. Absent a stated grade, confirm suitability by NMR/LC-MS/GC as needed.
• Stabilizers/Inhibitors: None stated for this item. Many triarylmethanes are stable as solids without added stabilizers; verify CoA if inhibitor content matters for your work.
• UV/trace metal/water/peroxide limits: Not specified for this item; refer to CoA/Spec Sheet.
• Batch-specific documentation: Request the Certificate of Analysis for purity assay, residual solvent profile, and any chromatographic data. For scale-up or regulatory submissions, inquire about available analytical methods (qNMR, HPLC, ICP-OES) and impurity profiling.
• Fitness-for-use tips:
  • For cross-couplings or electronic-materials applications, consider reprecipitation or short silica plug to remove trace colored impurities.
  • If ultra-dry material is required, dry under high vacuum (rt–40 °C) before use and handle under inert gas, consistent with item storage guidance (argon).

Reaction & Applications

4-Tritylaniline is a sterically encumbered aryl amine and useful building block for organic synthesis, materials chemistry, and dye/intermediate preparation.

• Representative applications (literature/general):
  • Precursor to triarylmethane dyes and triarylmethyl (trityl) cations/radicals under strongly acidic or oxidative conditions; para-amino substitution modulates color and stability.
  • N-functionalization: acylation, sulfonylation, and carbamate formation to access amide/sulfonamide libraries with a bulky aryl core (improves solubility and glass transition in materials).
  • Electrophilic diazotization (NaNO2/HCl, 0–5 °C) to the diazonium salt, enabling azo coupling to yield highly conjugated azo dyes/pigments.
  • As a nucleophile in metal-catalyzed C–N cross-coupling (Buchwald–Hartwig) to form diaryl or triaryl amines on the nitrogen.
  • Oxidative or Lewis acid-mediated functionalization at the triarylmethyl center (e.g., formation of trityl halides or cations) for further substitution.
• Practical tips:
  • The para trityl substituent is strongly deactivating sterically; electrophilic aromatic substitution on the aniline ring is suppressed versus aniline; reactions should target the nitrogen or the benzylic/trityl center.
  • Maintain inert atmosphere (argon) per Product Data to minimize discoloration; some triarylmethanes darken on air/light exposure.
  • For cross-couplings, choose ligands tolerant of bulky amines (e.g., BrettPhos/XPhos) and employ bases such as NaOtBu or Cs2CO3 in toluene/dioxane.
• Characterization: 1H NMR shows characteristic aniline NH2 (broad, exchangeable) and multiple aromatic resonances; 13C NMR features a downfield quaternary triarylmethyl carbon.

Reaction Conditions

Typical conditions below are literature/general guidance for reactions involving aryl anilines and triarylmethyl systems; optimize for your substrate set. These are not product specifications.

• N-Acylation and sulfonylation:

  • Solvents: DCM, THF, EtOAc, or toluene.
  • Bases: pyridine, triethylamine, or DIPEA (1.5–3.0 equiv).
  • Temperature: 0–25 °C for acyl chlorides/anhydrides; 1–3 h typical to completion by TLC.
  • Notes: Cool initial addition; the bulky substrate may require longer times or higher dilution.

• Buchwald–Hartwig N-arylation (as amine coupling partner):

  • Catalyst: Pd2(dba)3 (1–2 mol% Pd) or Pd(OAc)2 with bulky ligands (BrettPhos, XPhos 3–6 mol%).
  • Base: NaOtBu, KOtBu, or Cs2CO3 (2–3 equiv).
  • Solvent: toluene, 1,4-dioxane, or tert-amyl alcohol; DMF/DMAc for challenging aryl halides.
  • Temperature: 80–110 °C; 6–18 h. Sterics may necessitate higher catalyst loading.

• Diazotization/azo coupling (derivatization route):

  • Generate diazonium with NaNO2 (1.1 equiv) in 2–6 M HCl at 0–5 °C; couple with activated aromatics/phenols in mildly basic media. The para position is occupied; use for N→N2+ conversions followed by alternative transformations.

• Triarylmethyl functionalization:

  • Lewis/Brønsted acids (e.g., BF3·OEt2, AlCl3, TfOH) at 0–25 °C can form triarylmethyl cations/halides; monitor for dye-like coloration and control stoichiometry to avoid overreaction.

Always evaluate on small scale and monitor by TLC/NMR/LC-MS.

Safety & Handling

• GHS/CLP information: Not specified for this item; refer to SDS for authoritative hazard classification, pictograms, and H-statements.
• General hazards (aromatic amines, literature/generic): May cause skin/eye irritation and respiratory irritation upon dust generation. Avoid inhalation of dust and contact with skin/eyes. Handle in a fume hood.
• PPE: Laboratory coat, safety goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use dust mask/respirator if dusts/aerosols may form; select per SDS and risk assessment.
• Handling notes:
  • Product Data indicates storage under argon; minimize exposure to air and moisture to prevent oxidative discoloration or surface oxidation typical of triarylmethane derivatives.
  • Avoid strong oxidizing acids (which can generate triarylmethyl cations) and powerful electrophiles without proper controls.
  • Prevent dust formation; use antistatic measures when transferring.
• First aid (overview; defer to SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: wash with soap and water; remove contaminated clothing.
  • Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical advice if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Combustible organic solid. Use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and nitrogen oxides. Keep away from ignition sources.

Solvent Selection

As a highly aromatic, nonpolar-to-weakly basic solid, 4-tritylaniline dissolves in many organic solvents but is essentially water-insoluble.

• Polarity/miscibility (literature/general):
  • Water: negligible solubility.
  • Good: dichloromethane (DCM), chloroform, toluene, benzene, THF, 1,4-dioxane.
  • Very good in polar aprotics: DMF, DMAc, NMP, DMSO (useful for coupling chemistry or electrochemistry).
  • Alcohols: moderate solubility in MeOH/EtOH; improves with heat.
• Choosing a solvent by task:
  • Electrophilic/N-acylation chemistry: use DCM, THF, or EtOAc with an organic base (e.g., pyridine, DIPEA); cool if exothermic.
  • Metal-catalyzed C–N coupling (as nucleophile): toluene, dioxane, or tert-amyl alcohol are common, or polar aprotics (DMF/DMAc) for difficult substrates.
  • Crystallization and purification: hot toluene, xylene, or EtOH/IPA mixed with a poorer solvent (hexanes) to induce crystallization.
• Practical notes:
  • Avoid strongly acidic aqueous media if the triarylmethyl center’s stability is a concern; strong acids can generate colored triarylmethyl cations.
  • For spectroscopic work, CDCl3, d6-DMSO, or d8-THF provide good solubility.
• Quick comparison (literature/guidance):
  • DCM vs EtOAc: DCM dissolves faster and at lower volume; EtOAc is greener and often suitable for acylations and workups.
  • Toluene vs 1,4-dioxane: toluene is less polar and easier to remove; dioxane offers higher polarity for catalyst solvation.

Storage & Reconstitution

• Storage conditions (from Product Data): Room temperature, Argon charged. Store tightly closed under an inert atmosphere (argon recommended). Keep dry and away from strong acids/oxidants.
• Shipping (from Product Data): Shipped at ambient temperature (Normal).
• Stability notes (general): Triarylmethane derivatives are typically stable solids but may slowly discolor upon prolonged exposure to air/light. For long-term storage, protect from light, limit headspace oxygen, and avoid humidity.
• Reconstitution/dissolution (general):
  • Readily dissolves in organic solvents such as DCM, CHCl3, toluene, THF, and polar aprotics (DMF, DMSO). Begin with 5–20 mg/mL and adjust as needed.
  • For moisture-sensitive operations, dry the solid under high vacuum (rt–40 °C) before use and employ anhydrous solvents.
• Handling after opening: Purge container with argon before re-closing. Use clean, dry spatulas. If material cakes due to static or minor moisture pickup, gently granulate under inert gas.
• Shelf life: Not specified for this item; refer to CoA/Spec Sheet.

Always consult the product SDS for detailed safety and disposal guidance. Research use only, as noted in the Product Data.

Structure & Identity

4-Tritylaniline is a para-substituted aniline bearing a bulky triphenylmethyl (trityl) substituent on the aniline ring.

• Item-specific identifiers (from Product Data):

  • CAS: 22948-06-7
  • CID: 89914
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature structural data (for 4-tritylaniline):

  • Molecular formula: C25H21N (literature)
  • Molecular weight: ~335.45 g/mol (literature)
  • 2D structure (description): an aniline ring (–NH2 at position 1) with a para (4-) substitution by a triphenylmethyl group, i.e., a central quaternary carbon attached to three phenyl rings and to the para carbon of the aniline ring. Functional groups: primary aniline (electron-donating), multiple aromatic rings (four phenyls total), benzylic quaternary carbon (triarylmethyl center).
  • Representative SMILES (literature): Nc1ccc(cc1)C(c2ccccc2)(c3ccccc3)c4ccccc4

• Structural features and implications (general):

  • The strongly electron-donating –NH2 group and extensive aryl conjugation impart high aromatic electron density.
  • The trityl moiety is sterically demanding, influencing reactivity (e.g., attenuates electrophilic substitution on the aniline ring and impacts cross-coupling site selectivity).

Synthetic Utility

The molecule combines a reactive aniline nitrogen with a sterically demanding triarylmethyl substituent para to the amine, offering distinct reactivity handles.

• Transformations at nitrogen (literature/general):

  • Acylation/carbamoylation/sulfonylation to furnish amides, ureas/carbamates, and sulfonamides. Bulky para trityl may enhance crystallinity and lipophilicity of products.
  • Metal-catalyzed N-arylation (Buchwald–Hartwig) to access diaryl/triaryl anilines. Use bulky, electron-rich ligands to accommodate sterics.

• Aromatic ring chemistry:

  • Direct electrophilic substitution is disfavored by steric congestion; diazotization at the aniline nitrogen provides an alternative to functionalize the para position indirectly (via diazonium coupling), though the para site is already occupied by trityl.
  • Directed ortho-metalation adjacent to –NH2 (after formation of an amide/sulfonamide directing group) may enable ortho-functionalization, but steric hindrance must be considered.

• Triarylmethyl center chemistry:

  • Under strong Brønsted/Lewis acids, generation of triarylmethyl cations enables substitution (e.g., halogenation to trityl halides) and dye synthesis.
  • Oxidative routes to persistent triarylmethyl radicals are documented for related systems; the para-amino group tunes stability and redox properties.

• Retrosynthetic value:

  • Serves as a convergent node to introduce a trityl core late-stage onto an aniline, or as a bulky amine component to control aggregation and packing in materials chemistry.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological targeting reagent. No antigen/epitope, clone, isotype, or species reactivity information applies. None provided in the Product Data.