Benzenamine, 4-methyl-N-(4-methylphenyl)-
DMDPA · DI-P-Tolyamine · Di-p-toL · Ditlylamine · DI-P-TOLYLAMINE · p,p'-Ditolyamine · P,P'-DITLYLAMINE · P,P'-DITOLYLAMINE
Identifiers & Physical Properties
| CAS No. | 620-93-9 |
|---|---|
| Molecular formula | C14H15N |
| Average molar mass | 197.27 g/mol |
| Monoisotopic mass | 197.12044948 g/mol |
| SMILES | Cc1ccc(Nc2ccc(C)cc2)cc1 |
| InChIKey | RHPVVNRNAHRJOQ-UHFFFAOYSA-N |
| PubChem CID | 69293 |
| EC No. | 210-659-8 |
| DTXSID | DTXSID5060726 |
Chemical & Physical Properties
| XLogP | 4.2 |
|---|---|
| Topological polar surface area | 12 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 2 |
| Heavy atoms | 15 |
| Formal charge | 0 |
| Complexity | 154 |
| SpringerMaterials Properties | Density |
| Melting point | 78-82°C |
| Boiling point | 330 °C |
| Density | 1.0514 (rough estimate) |
| Refractive index | 1.6095 (estimate) |
| Storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| Solubility | Chlorofrm (Slightly), Methanol (Slightly) |
| Physical state | Solid |
| pKa (acidity coefficient) | 1.68±0.40(Predicted) |
| Color | Off-White |
| InChI | InChI=1S/C14H15N/c1-11-3-7-13(8-4-11)15-14-9-5-12(2)6-10-14/h3-10,15H,1-2H3 |
| InChIKey | RHPVVNRNAHRJOQ-UHFFFAOYSA-N |
| SMILES | C1(NC2=CC=C(C)C=C2)=CC=C(C)C=C1 |
| CAS DataBase Reference | 620-93-9(CAS DataBase Reference) |
| EPA Substance Registry System | 4,4'-Dimethyldiphenylamine (620-93-9) |
| UNSPSC Code | 12352103 |
| NACRES | NA.23 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302+H312+H332-H315-H319 |
| GHS precautionary statements | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29214990 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | WarningH302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (33.3%) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29214990 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302+H312+H332-H315-H319 |
| GHS precautionary statements | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501 |
Applications & Uses
Description
Di-p-tolylamine (also known as 4,4′-dimethyldiphenylamine) is an intermediate for OLED materials. Acting as a strong electron-donating unit, Di-p-tolylamine is chemically incorporated into the molecular framework of the host material POPCPA, and is used to fabricate highly efficient blue phosphorescent OLED devices with low driving voltages (maximum power efficiency of 45.3 lm/W; driving voltage of 2.6 V at 1 cd/m2). This compound shares a similar diphenylamine structure to that found in commonly used hole-transporting materials (such as TAPC); the methyl-substituted diphenylamine unit possesses good electron-donating ability and steric hindrance, which helps to increase the material's glass transition temperature (90°C) and thermal decomposition temperature (406°C), thereby enhancing the thermal stability of the device[1].
Uses
4,4''-Dimethyldiphenylamine is a reagent used in the comparative studies of the analgesic and anti-inflammatory properties of N-phenylanthranilic acids and mefenamic acid, and the anti parasitic activities of some substituted diphenylamines.
Preparation & Synthesis
Preparation
The first method: Since the reaction of aryl halides with primary aromatic amines produces not only diaryl amines but also triaryl amines, the reaction of p-iodotoluene and p-toluidine to produce Di-p-tolylamine simultaneously generates a large amount of 4,4',4''-trimethyltriphenylamine. The second method: Di-p-tolylamine is prepared by acylation of p-toluidine followed by reaction with p-iodotoluene, and finally hydrolysis. This reaction overcomes the shortcomings of the direct reaction between aryl halides and primary aromatic amines; although the yield is low, it does not produce 4,4',4''-trimethyltriphenylamine.