Triphenylamine

Base Information

• Chemical Name: Triphenylamine
• CAS No.: 603-34-9
• Deprecated CAS: 149006-34-8
• Molecular Formula: C18H15N
• Molecular Weight: 245.324
• Hs Code.: 29214980
• European Community (EC) Number: 210-035-5
• ICSC Number: 1366
• NSC Number: 66458
• UNII: NJS65M2DS2
• DSSTox Substance ID: DTXSID4022076
• Nikkaji Number: J54.231H
• Wikipedia: Triphenylamine
• Wikidata: Q7843272
• ChEMBL ID: CHEMBL3819197
• Mol file: 603-34-9.mol

Synonyms:TRIPHENYLAMINE;603-34-9;N,N-Diphenylaniline;Benzenamine, N,N-diphenyl-;Triphenyl amine;N,N-Diphenylbenzenamine;Amine, triphenyl;CCRIS 4887;HSDB 2098;EINECS 210-035-5;NSC 66458;UNII-NJS65M2DS2;NJS65M2DS2;AI3-17278;MFCD00003020;NSC-66458;N,N,N-Triphenylamine;N,N-Diphenylbenzeneamine;diphenylaniline;Trifenilamina;Trifenylamin;Trisphenylamine;4-diphenylaminobenzene;880462-20-4;Triphenylamine, 98%;Benzenamine,N-diphenyl-;N,N,N-Triphenylamine #;Bencenamina, n, n-difenil-;SCHEMBL30959;BIDD:GT0660;CHEMBL3819197;DTXSID4022076;N,N-diphenylaniline;Triphenylamine;N,N-DIPHENYLANILINE [HSDB];ADAL1012817;NSC66458;AKOS015840682;CS-W012714;LS-1437;SB66357;AC-13457;AS-14885;SY005738;FT-0632501;T0507;EN300-114099;Triphenylamine, Vetec(TM) reagent grade, 98%;A832698;Q7843272;W-105262

Chemical Property of Triphenylamine

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 1.62E-05mmHg at 25°C
• Melting Point: 124-128 °C(lit.)
• Refractive Index: 1.3530 (estimate)
• Boiling Point: 365 °C at 760 mmHg
• PKA: -3.04±0.30(Predicted)
• Flash Point: 157.3 °C
• PSA: 3.24000
• Density: 1.112 g/cm³
• LogP: 5.15640
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly)
• Water Solubility.: insoluble
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 245.120449483
• Heavy Atom Count: 19
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

Triphenylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38-36/37/38-38-36
• Safety Statements: 26-28-37/39-26,37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: C1=CC=C(C=C1)N(C2=CC=CC=C2)C3=CC=CC=C3
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes and skin.
• Uses: Organic light-emitting diode (OLED) devices have received much attention, because they are expected to be a next generation display and light source, thanks to lightweight and flexible organic materials. Triphenylamine is a propeller-like structural chromophore with a nitrogen atom center. The compound 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. It is used in the manufacture of photographic film. Triphenylamines (TPAs) 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. It is coated on film bases as primary photoconductor. It is coated on photographic film, where it acts as photoconductor. Triphenylamine is used in organic light-emitting diode as hole-transporters and as a pharmaceutical intermediate. It is coated on film bases as primary photoconductor.

Technology Process of Triphenylamine

There total 146 articles about Triphenylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

bromobenzene (108-86-1,52753-63-6) + diphenylamine (122-39-4) → N,N-diphenylaminobenzene (603-34-9)

Guidance literature:

With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate; In toluene; at 20 ℃; for 1h;

DOI:10.1021/jo025732j

Reference yield: 99.0%

diphenylamine (122-39-4) + chlorobenzene (108-90-7) → N,N-diphenylaminobenzene (603-34-9)

Guidance literature:

With palladium diacetate; sodium t-butanolate; ruphos; In neat (no solvent); at 110 ℃; for 12h; Green chemistry;

DOI:10.1002/ejoc.201402077

Reference yield: 99.0%

aniline (62-53-3) + chlorobenzene (108-90-7) → N,N-diphenylaminobenzene (603-34-9)

Guidance literature:

With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate; In neat (no solvent); at 110 ℃; for 12h; Reagent/catalyst; Inert atmosphere; Green chemistry;

DOI:10.1002/ejoc.201501616

upstream raw materials:

bromobenzene

potassium diphenylamide

2-(N,N-diphenylamino)benzoic acid

N,N'-ditrityl-hydrazine

Downstream raw materials:

[4-(4-Nitro-phenylazo)-phenyl]-diphenyl-amine

[4-(2,4-Dinitro-phenylazo)-phenyl]-diphenyl-amine

[4-(4-Methoxy-phenylazo)-phenyl]-diphenyl-amine

4,4′-bis(diphenylamino)benzophenone

Refernces

• 1、 Pine,S.H.. "-". . p. 2554 - 2555. Retrieved 1968.
• 2、 Van Willigen. "". . p. 2229. Retrieved 1967.
• 3、 Corma,Fornes,Galletero,Garcia,Gomez-Garcia. "Prevalence of the external surface over the internal pores in the spontaneous generation of tetrathiafulvalene radical cation incorporated in the novel delaminated ITQ-2 zeolite". . p. 1218 - 1222. Retrieved 2001.
• 4、 Hajipour, Abdol R.,Khorsandi, Zahra,Sarfjoo, Mohamad Reza,Varma, Rajender S.. "A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib". supporting information. p. 5222 - 5229. Retrieved 2021/07/29.
• 5、 Ma, Ruixuan,Qin, Jianhua,Shi, Lei,Zhang, Xinhai. "A base-free Chan–Lam reaction catalyzed by an easily assembled Cu(II)-carboxylate metal-organic framework". . p. 795 - 799. Retrieved 2021/07/06.