20927-98-4

Basic information

• Product Name: 2-(p-tolyloxy)aniline
• Synonyms: 2-(p-tolyloxy)aniline;Einecs 244-115-6;2-(4-Methylphenoxy)benzenamine
• CAS NO: 20927-98-4
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 199.24842
• EINECS: 244-115-6
• Mol File: 20927-98-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 92-93 °C
• Boiling Point: 305.7 °C at 760 mmHg
• Flash Point: 138.1 °C
• Appearance: /
• Density: 1.115 g/cm³
• Vapor Pressure: 0.000809mmHg at 25°C
• Refractive Index: 1.608
• PKA: 4.10±0.10(Predicted)
• CAS DataBase Reference: 2-(p-tolyloxy)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(p-tolyloxy)aniline(20927-98-4)
• EPA Substance Registry System: 2-(p-tolyloxy)aniline(20927-98-4)

Safety Data

• Hazardous Substances Data: 20927-98-4(Hazardous Substances Data)

Usage

General Description

2-(p-Tolyloxy)aniline is a chemical compound with the molecular formula C13H13NO. It is an aniline derivative with a para-tolyl group attached to the oxygen atom. 2-(p-Tolyloxy)aniline is commonly used as an intermediate in the synthesis of various dyes and pigments. It is also employed in organic reactions and as a building block in the pharmaceutical industry. The presence of the para-tolyl group makes it useful in the development of new materials and as a precursor to more complex organic molecules. However, it is important to handle this compound with care, as exposure to it can cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C13H13NO/c1-10-6-8-11(9-7-10)15-13-5-3-2-4-12(13)14/h2-9H,14H2,1H3

Upstream product

• 3402-70-8 1-nitro-2-(p-tolyloxy)benzene 
• 106-44-5 p-cresol 
• 1493-27-2 ortho-nitrofluorobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 1192-96-7 potassium p-cresolate 

Downstream Products

• 1706-12-3 4-phenoxytoluene 
• 860517-66-4 (2-p-tolyloxy-phenyl)-arsonic acid 
• 128643-14-1 N-[2-(4-methylphenoxy)phenyl]acetamide 
• 102078-85-3 benzoic acid-(2-p-tolyloxy-anilide) 
• 133437-36-2 [1-Phenyl-meth-(E)-ylidene]-(2-p-tolyloxy-phenyl)-amine 
• 76838-19-2 1-Benzoyl-3-(2-p-tolyloxy-phenyl)-thiourea 
• 133437-34-0 2-allylamino-4'-methyldiphenyl ether 
• 206262-15-9 2-(4-methylphenoxy)benzenesulfonyl chloride 
• 76839-01-5 (2-p-Tolyloxy-phenyl)-thiourea 
• 76840-94-3 Imidazolidin-2-ylidene-(2-p-tolyloxy-phenyl)-amine 
• 87671-67-8 2-[(4-methylphenyl)amino]phenol 
• 133437-35-1 2-benzylamino-4'-methyldiphenyl ether 
• 106-49-0 p-toluidine 

Relevant articles and documents

NOVEL TRIAZINE COMPOUND, AND ORGANIC ELECTRONIC ELEMENT AND PLANT-GROWING LIGHTING THAT USE THE SAME

PROBLEM TO BE SOLVED: To provide a triazine compound which has a high triplet energy level and excellent heat resistance, and can be used as an organic electronic element material realizing an element with high efficiency, low voltage and a long life. SOLUTION: In the triazine compound, as represented by the general formula [1] in the figure, a triazine backbone moiety is linked to a dibenzofuran or dibenzothiophene backbone moiety via a biphenyl backbone moiety, where X is an oxygen atom or sulfur atom. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

Access to Chiral Seven-Member Cyclic Amines via Rh-Catalyzed Asymmetric Hydrogenation

A highly efficient asymmetric hydrogenation of azepine/oxazepine-type seven-member cyclic imine hydrochlorides was successfully developed using Rh/bisphosphine-thiourea ligand ZhaoPhos, affording various chiral seven-member cyclic amines with full conversions, high yields, and excellent enantioselectivities (up to 96% yield, >99% ee). Additionally, this asymmetric hydrogenation can proceed well on gram scale with excellent ee value. Moreover, control experimental results displayed that the anion-bonding interaction between the chloride ion of the substrate and thiourea motif of the ZhaoPhos played an important role to obtain excellent enantioselectivity.

Additivity of substituent effects in aromatic stacking interactions

The goal of this study was to experimentally test the additivity of the electrostatic substituent effects (SEs) for the aromatic stacking interaction. The additivity of the SEs was assessed using a small molecule model system that could adopt an offset face-to-face aromatic stacking geometry. The intramolecular interactions of these molecular torsional balances were quantitatively measured via the changes in a folded/unfolded conformational equilibrium. Five different types of substituents were examined (CH3, OCH3, Cl, CN, and NO2) that ranged from electron-donating to electron-withdrawing. The strength of the intramolecular stacking interactions was measured for 21 substituted aromatic stacking balances and 21 control balances in chloroform solution. The observed stability trends were consistent with additive SEs. Specifically, additive SE models could predict SEs with an accuracy from ±0.01 to ±0.02 kcal/mol. The additive SEs were consistent with Wheeler and Houk's direct SE model. However, the indirect or polarization SE model cannot be ruled out as it shows similar levels of additivity for two to three substituent systems, which were the number of substituents in our model system. SE additivity also has practical utility as the SEs can be accurately predicted. This should aid in the rational design and optimization of systems that utilize aromatic stacking interactions.