17075-03-5

Basic information

• Product Name: 4-AMINOPYRENE
• Synonyms: 4-AMINOPYRENE;PYREN-4-YLAMINE;4-pyrenamine;pyren-4-amine
• CAS NO: 17075-03-5
• Molecular Formula: C₁₆H₁₁N
• Molecular Weight: 217.27
• Mol File: 17075-03-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 207 °C
• Boiling Point: 440.8 °C at 760 mmHg
• Flash Point: 246.2 °C
• Appearance: /
• Density: 1.322 g/cm³
• Vapor Pressure: 5.71E-08mmHg at 25°C
• Refractive Index: 1.904
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly)
• PKA: 4.32±0.30(Predicted)
• CAS DataBase Reference: 4-AMINOPYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOPYRENE(17075-03-5)
• EPA Substance Registry System: 4-AMINOPYRENE(17075-03-5)

Safety Data

• RTECS: UR2277000
• Hazardous Substances Data: 17075-03-5(Hazardous Substances Data)

Usage

Description

4-Aminopyrene is a pyrene derivative, characterized by the presence of an amino group attached to the pyrene structure. This organic compound is known for its unique chemical properties and potential applications in various fields.

Uses

Used in Chemical Synthesis:
4-Aminopyrene is used as a reagent in the preparation of pyrroles, specifically through the Paal-Knorr synthesis. This method involves the reaction of diketones with amines, where 4-aminopyrene serves as a key component in the synthesis process.
In the Paal-Knorr synthesis, 4-aminopyrene reacts with diketones to form intermediate compounds, which upon further cyclization and dehydration, yield the desired pyrrole structures. This approach is particularly useful for the synthesis of pyrroles with specific functional groups and structural features, making 4-aminopyrene a valuable reagent in organic chemistry.
Overall, 4-aminopyrene plays a significant role in the synthesis of pyrroles, contributing to the development of new compounds with potential applications in various industries, such as pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C16H11N/c17-14-9-12-5-1-3-10-7-8-11-4-2-6-13(14)16(11)15(10)12/h1-9H,17H2

Upstream product

• 22245-47-2 4-acetylpyrene 
• 6217-22-7 pyrene-4,5-dione 
• 129-00-0 pyrene 
• 57835-92-4 4-nitropyrene 
• 88535-47-1 4-nitro-1,2,3,6,7,8-hexahydropyrene 
• 1732-13-4 1,2,3,6,7,8-hexahydropyrene 
• 31700-39-7 1-hydroxypyrene 

Relevant articles and documents

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Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage

The Br?nsted acid-catalyzed synthesis of primary amines from acetyl arenes and alkanes with C-C bond cleavage is described. Although the conversion from an acetyl group to amine has traditionally required multiple steps, the method described herein, which uses an oxime reagent as an amino group source, achieves the transformation directly via domino transoximation/Beckmann rearrangement/Pinner reaction. The method was also applied to the synthesis of γ-aminobutyric acids, such as baclophen and rolipram.

Phototransformations of environmental contaminants in models of the aerosol: 2 and 4-Nitropyrene

A comparative photochemical study of 2- and 4-nitropyrene (2- and 4-NO2Py) in different organic solvents was performed in order to provide information on the fate of these contaminants in models of the atmospheric aerosols. The isomers presented small photodegradation yields, 10?4–10?5 for 4-NO2Py and 10?5–10?6 for 2-NO2Py, demonstrating the low reactivity of the excited states and intermediate species that participate in their photodegradation. Photoproducts such as 4,5-pyrenedione, 4-hydroxypyrene, aminopyrene and pyrene were identified during the irradiation of 4-NO2Py. Substantial differences were observed in the photodegradation yields, and type and relative yields of the photoproducts of the 2-NO2Py and 4-NO2Py when compared to those of 1-NO2Py. These differences were related with the orientation of the nitro group and with differences in intersystem crossing rates which affect the yields of the pyrenoxy radical (PyO) and of the (π,π*) triplet state, principal precursors in their photodegradation. The smallest photodegradation yield was for 2-NO2Py due to the lack of interaction between the nitro group and the aromatic moiety thus resulting in a low yield of formation of the PyO radical. In the presence of O2, the photodegradation quantum yields of 4-NO2Py were reduced in all solvents due the quenching of the (π,π*) triplet state, and 4-aminopyrene was not observed thus demonstrating that its formation occurs from this state. These results suggest that in atmospheric aerosols containing an organic liquid-like layer, the nitropyrene isomers will show low photoreactivity resulting in an increase in their residence time in the atmosphere. An increase in reactivity is expected when the excited nitropyrenes are nearby substances with hydrogen donor capacities such as phenols. The photoproducts formed in the transformation could increase the toxicity of the particulate matter in the atmosphere.