TRIPHENYLAMINE

Triphenylamine is a key aromatic building block known for its rigid three-phenyl structure and useful electronic properties.
Triphenylamine is frequently incorporated into hole-transport materials, light-emitting compounds, and donor–acceptor molecular systems.
Triphenylamine's tunable structure also makes it valuable for designing high-performance dyes, sensors, and functional organic materials.

CAS Number: 603-34-9
EC Number: 210-035-5
Molecular Formula: C18H15N
Molecular Weight: 245.32 g/mol

Synonyms: TRIPHENYLAMINE, N,N-Diphenylaniline, Benzenamine, N,N-diphenyl-, Triphenyl amine, N,N-Diphenylbenzenamine, Amine, triphenyl, CCRIS 4887, UNII-NJS65M2DS2, HSDB 2098, AI3-17278, EINECS 210-035-5, NJS65M2DS2, NSC 66458, N,N-DIPHENYLANILINE [HSDB], NSC-66458, DTXSID4022076, N,NDiphenylaniline, N,NDiphenylbenzenamine, RefChem:191895, Triphenyl amine (ACGIH), DTXCID702076, Benzenamine, N,N-diphenyl-(9CI), 210-035-5, InChI=1/C18H15N/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15, ODHXBMXNKOYIBV-UHFFFAOYSA-N, 603-34-9, diphenylaniline, MFCD00003020, Benzenamine,N-diphenyl-, SCHEMBL30959, BIDD:GT0660, AKOS015840682, CS-W012714, T0507, N,N,N-Triphenylamine, triphenyl-amine, N,N-Diph, Triphenylamine, 98%, aniline, N,N-diphenyl-, N,N,N-Triphenylamine #, A832698, SCHEMBL128446, SCHEMBL128447, SCHEMBL453160, orb3177382, SCHEMBL1378606, SCHEMBL1499945, SCHEMBL1568122, SCHEMBL5536229, SCHEMBL9622532, CHEMBL3819197, NSC66458, SBB058989, FT32359, SB66357, AC-13457, AS-14885, ST081372, SY005738, DB-002823, NS00034334, EN300-114099, Triphenylamine, Vetec(TM) reagent grade, 98%, F211897, Q7843272, 25656-58-0, 210-035-5, 603-34-9, Benzenamine, N,N-diphenyl-, N,N,N-Triphenylamine, N,N-Diphenylanilin, N,N-Diphenylaniline, N,N-Diphénylaniline, trifenilamina, Triphenylamine, 4-(4-HYDROXYPHENYL)THIOMORPHOLINE 1,1-DIOXIDE, 880462-20-4, 97%, Amine, triphenyl, EINECS 210-035-5, N,N-di(phenyl)aniline, N,N-Diphenylbenzenamine, N,N-diphenylbenzeneamine, N-Diphenylbenzenamine, tri(phenyl)amine, Triphenyl amine, Triphenyl-amine, Triphenylamine-d15, Trisphenylamine

Triphenylamine is an aromatic tertiary amine composed of a central nitrogen atom bonded to three phenyl groups.
Triphenylamine is widely used as a structural building block in organic electronics because of its electron-donating character, good charge-transport properties, and ability to form stable radical cations.
Triphenylamine derivatives are especially important in OLEDs, organic solar cells, hole-transport materials, dyes, and advanced optoelectronic systems.

Triphenylamine is an organic compound with formula (C6H5)3N.
In contrast to most amines, triphenylamine is nonbasic.

At room temperature Triphenylamine appears as a colorless crystalline solid, with monoclinic structure.
Triphenylamine is well miscible in diethyl ether and benzene, but it is practically insoluble in water, and partially in ethanol.

Triphenylamine's derivatives have useful properties in electrical conductivity and electroluminescence, and they are used in OLEDs as hole-transporters.
Triphenylamine can be prepared by Ullmann arylation of diphenylamine.

Triphenylamine is used in organic light-emitting diode as hole-transporters and as a pharmaceutical intermediate.
Triphenylamine is coated on film bases as primary photoconductor.

Uses of Triphenylamine:
Triphenylamine is used in organic light-emitting diode as hole-transporters and as a pharmaceutical intermediate.
Triphenylamine is coated on film bases as primary photoconductor.

Triphenylamine is a propeller-like structural chromophore with a nitrogen atom center.
Triphenylamine has a large steric hindrance and hyper conjugation electronic effect, which can enhance the stability of the nitrogen atomic radical.

Triphenylamine materials also have a high hole mobility due to their unique free radicals nature.
Many hole transport materials based on triphenylamine derivatives (TPD) are widely usable,because they are heat-resistant and amorphous.

In addition to the TPDs, oxadiazole derivatives (PBD) having an electron transport property, Alq3 as a host material,and blue emissive distylyl derivatives are fundamental materials for amorphous OLED devices.
Triphenylamine is used in the manufacture of photographic film.

Triphenylamines are highly fluorescent compounds that are efficient to induce cell death upon visible light excitation.
Triphenylamine is used in organic light-emitting diode as hole-transporters and as a pharmaceutical intermediate.
Triphenylamine is coated on film bases as primary photoconductor.

Applications of Triphenylamine:
Triphenylamine serves an essential role in the development of organic light-emitting diode (OLED) devices, which have garnered significant attention as potential next-generation displays and light sources.
Triphenylamine's distinctive propeller-like structure, centered around a nitrogen atom, contributes to its high hole mobility due to its stability and electronic properties.

This makes triphenylamine an exceptional choice for use in OLEDs, where it functions as an efficient hole transporter.
Triphenylamine's robust performance is further supported by its heat-resistant and amorphous nature, making it a valuable component in enhancing OLED efficiency and lifespan.
Additionally, triphenylamine finds application as a pharmaceutical intermediate and a primary photoconductor coating on film bases, showcasing its versatility and importance in various industries.

Triphenylamine is used in organic light-emitting diode as hole-transporters and as a pharmaceutical intermediate.
Triphenylamine is coated on film bases as primary photoconductor.

Photoinitiators for Hydrogel Formation:
Triphenylamine derivatives are used as novel D-pi-A hemicyanine dyes, acting as effective photoinitiators for in situ hydrogel formation and DLP printing, expanding their applications in biomedical engineering and 3D printing technologies.

Supramolecular Photosensitizers:
A supramolecular construct based on triphenylamine and pyrazine demonstrates aggregation-induced emission properties, enhancing the efficiency of photooxidation reactions.
This development offers potential improvements in photodynamic therapy and environmental applications.

Highly Efficient OLEDs:
Triphenylamine is integral in synthesizing new phenanthro[9,10-d]oxazole-based fluorophores with hybridized local and charge-transfer characteristics.
These materials are crucial for developing blue non-doped OLEDs with minimal efficiency roll-off, significant for advanced display technologies.

Memory Device Applications:
Modifications in donor end caps in N-heteroaromatic systems containing triphenylamine were explored for binary-to-ternary WORM memory conversion, contributing to advancements in memory storage technology.

Chemical Properties of Triphenylamine:
Triphenylamine has three aromatic groups directly linked to the central nitrogen atom.
Each aromatic group acts as an electron attractor, directing the electron cloud of the lone pair of nitrogen towards it.

With the delocalization of the nitrogen lone pair a partial positive charge is conferred to nitrogen, counterbalanced by the partial negative charge localized on the aromatic groups.
This arrangement hinders nitrogen protonation, rendering triphenylamine an extremely weak base.

From this characteristic, moreover, Triphenylamine follows that the three N-C bonds all lie in the same plane and that they are located at 120° from each other, which is not the case with aliphatic amines and ammonia, where the orbitals of nitrogen are arranged in a tetrahedron.
Due to steric hindrance, the phenyl groups are not on the same plane defined by the three N-C bonds, but are twisted, giving the molecule its characteristic "propeller-like" shape.[6]

Stability and Reactivity of Triphenylamine:

Chemical Stability:
Stable under normal ambient and recommended storage conditions.

Reactivity:
Generally low reactivity under normal handling conditions.

Conditions to Avoid:
Excessive heat, open flames, ignition sources, and prolonged exposure to incompatible substances.

Incompatible Materials:
Strong oxidizing agents and strong acids.

Hazardous Decomposition Products:
Thermal decomposition or combustion may produce carbon monoxide, carbon dioxide, nitrogen oxides, and irritating fumes.

Handling and Storage of Triphenylamine:

Safe Handling:
Avoid generating or inhaling dust and prevent contact with skin and eyes.
Use adequate ventilation and follow good industrial hygiene practices.

Storage Conditions:
Store in a tightly closed container in a cool, dry, and well-ventilated area away from heat, ignition sources, and incompatible materials.

First Aid Measures of Triphenylamine:

Inhalation:
Move the affected person to fresh air.
Seek medical attention if symptoms persist.

Skin Contact:
Wash thoroughly with soap and water and remove contaminated clothing.

Eye Contact:
Rinse cautiously with plenty of water for several minutes.
Remove contact lenses if present and easy to do.

Ingestion:
Rinse mouth with water and seek medical advice if discomfort occurs.

Firefighting Measures of Triphenylamine:

Suitable Extinguishing Media:
Use dry chemical powder, carbon dioxide, foam, or water spray suitable for the surrounding fire.

Specific Hazards:
Combustion may generate carbon oxides, nitrogen oxides, and irritating smoke.

Protective Equipment:
Firefighters should wear self-contained breathing apparatus and suitable protective clothing.

Accidental Release Measures of Triphenylamine:

Personal Precautions:
Avoid dust formation, inhalation, and direct contact.
Ensure adequate ventilation and wear appropriate protective equipment.

Environmental Precautions:
Prevent release into drains, waterways, and soil.

Cleanup Methods:
Carefully sweep or collect spilled material without creating dust and place it in a suitable closed container for disposal.

Exposure Controls/Personal Protective of Triphenylamine:

Engineering Controls:
Provide adequate general or local exhaust ventilation.

Eye Protection:
Wear safety glasses or chemical safety goggles.

Hand Protection:
Use suitable chemical-resistant gloves.

Skin Protection:
Wear appropriate protective clothing.

Respiratory Protection:
Use a suitable particulate respirator if ventilation is insufficient or dust may be generated.

Hygiene Measures:
Wash hands thoroughly after handling and before eating, drinking, or smoking.

Identifiers of Triphenylamine:
Product Name: Triphenylamine
CAS No.: 603-34-9
Molecular Weight : 245.32
MDL No. : MFCD00003020
Purity/ Specification: 97%
Molecular Formula: C18H15N
Storage: Sealed in dry, room temperature
SMILES Code: N(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3

Product Number: T0507
Purity / Analysis Method : >98.0%(GC)
Molecular Formula / Molecular Weight: C18H15N = 245.33 
Physical State (20 deg.C): Solid
Storage Temperature : Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 603-34-9
Reaxys Registry Number: 2050487
PubChem Substance ID: 87576436
SDBS (AIST Spectral DB): 3093
MDL Number: 
MFCD00003020

CAS No.: 603-34-9
Chemical Name: Triphenylamine
CBNumber: CB9401415
Molecular Formula: C18H15N
Molecular Weight: 245.32
MDL Number: MFCD00003020

CAS Number: 603-34-9
Abbreviations: TPAPh3N
ChemSpider: 11282
ECHA InfoCard: 100.009.123
EC Number: 210-035-5
PubChem CID: 11775
RTECS number: YK2680000
UNII: NJS65M2DS2
CompTox Dashboard (EPA): DTXSID4022076
InChI: InChI=1S/C18H15N/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
Key: ODHXBMXNKOYIBV-UHFFFAOYSA-N
InChI=1/C18H15N/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
Key: ODHXBMXNKOYIBV-UHFFFAOYAF
SMILES: c3c(N(c1ccccc1)c2ccccc2)cccc3

Linear Formula: (C6H5)3N
CAS Number: 603-34-9
Molecular Weight: 245.32
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24900507
EC Number: 210-035-5
Beilstein/REAXYS Number: 2050487
MDL number: MFCD00003020
Assay: 98%

CAS: 603-34-9
IUPAC Name: N,N-diphenylaniline
Molecular Formula: C18H15N
InChI Key: ODHXBMXNKOYIBV-UHFFFAOYSA-N
SMILES: C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1
Molecular Weight (g/mol): 245.33

Properties of Triphenylamine:
Chemical formula: C18H15N
Molar mass: 245.325 g·mol−1
Appearance: Off-white solid
Density: 0.774 g/cm3
Melting point: 127 °C (261 °F; 400 K)
Boiling point: 347 to 348 °C (657 to 658 °F; 620 to 621 K)
Solubility in water: Almost insoluble
log P: 5.74

Quality Segment: 100
assay: 98%
bp: 347-348 °C (lit.)
mp: 124-128 °C (lit.)
SMILES string: c1ccc(cc1)N(c2ccccc2)c3ccccc3
InChI: 1S/C18H15N/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
InChI key: ODHXBMXNKOYIBV-UHFFFAOYSA-N

Molecular Weight: 245.3 g/mol
XLogP3: 5.7
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 3
Exact Mass: 245.120449483 Da
Monoisotopic Mass: 245.120449483 Da
Topological Polar Surface Area: 3.2 Ų
Heavy Atom Count: 19
Complexity: 202
Isotope Atom Count: 0
Computed by PubChem
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Melting Point: 127 °C
Solubility in water: Insoluble
Solubility (soluble in): Benzene, Ether, Toluene
Solubility (slightly sol. in): Ethanol

Melting point: 124-128 °C (lit.)
Boiling point: 347-348 °C (lit.)
Density: 0.7740
refractive index: 1.3530 (estimate)
Flash point: 365°C
storage temp.: Sealed in dry,Room Temperature
solubility: Chloroform (Slightly)
pka: -3.04±0.30(Predicted)
form: Crystalline Powder
color: Off-white to slightly beige
Water Solubility: insoluble
BRN: 2050487
Exposure limits: NIOSH: TWA 5 mg/m3
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
InChI: 1S/C18H15N/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
InChIKey: ODHXBMXNKOYIBV-UHFFFAOYSA-N
SMILES: c1ccc(cc1)N(c2ccccc2)c3ccccc3
CAS DataBase Reference: 603-34-9(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: NJS65M2DS2
NIST Chemistry Reference: Benzenamine, N,N-diphenyl-(603-34-9)
EPA Substance Registry System: Triphenylamine (603-34-9)
UNSPSC Code: 12352100
NACRES: NA.22

Specifications of Triphenylamine:
Appearance: White to Almost white powder to crystal
Purity(GC): min. 98.0 %
Melting point: 125.0 to 129.0 °C

Appearance (Color): White to pale cream
Melting Point (clear melt): 123.0-130.0?C
Form: Crystals or powder or crystalline powder
Assay (GC): ≥97.5%
Identification (FTIR): Conforms

Names of Triphenylamine:

Preferred IUPAC name:
N,N-Diphenylaniline

Other names:
Triphenylamine
N,N,N-Triphenylamine
N,N-Diphenylbenzeneamine