2-Nitrofluorenone N,N-dimethylaniline

Identification

Molecular formula

C₂₃H₂₀N₂O₂

CAS number

74335-64-1

IUPAC name

N,N-dimethyl-4-[(2-nitrofluoren-9-ylidene)methyl]aniline

State

Solid: At room temperature, this compound exists as a solid due to its large molecular structure and significant intermolecular forces, which include pi-stacking and dipole-dipole interactions. These interactions elevate the melting and boiling points considerably compared to smaller, non-polar molecules.

Melting point (Celsius)

180.00

Melting point (Kelvin)

453.15

Boiling point (Celsius)

475.00

Boiling point (Kelvin)

748.15

General information

Molecular weight

324.42g/mol

Molar mass

324.3560g/mol

Density

1.3200g/cm³

Appearence

The compound is typically a yellow to orange crystalline powder. The vibrant yellow-orange hue is indicative of its polycyclic aromatic structure coupled with the nitro functional group, which are both known to absorb visible light.

Comment on solubility

Solubility of N,N-dimethyl-4-[(2-nitrofluoren-9-ylidene)methyl]aniline

N,N-dimethyl-4-[(2-nitrofluoren-9-ylidene)methyl]aniline exhibits unique solubility characteristics that are quite intriguing.

Solubility Profile

This compound is known to possess limited solubility in water due to the presence of its bulky fluorenylidene group, which hinders proper interaction with water molecules. Solubility can vary significantly based on the solvent used:

Polar Solvents: The compound shows moderate solubility in polar organic solvents such as methanol and ethanol, making these solvents suitable for dilution and further reactions.
Non-Polar Solvents: It exhibits good solubility in non-polar solvents like toluene or chloroform, which is attributed to the hydrophobic characteristics of the fluorenyl moiety that enhances interaction with similar non-polar environments.

In general, it is crucial to consider the chemical structure and the nature of the solvents when assessing the solubility of N,N-dimethyl-4-[(2-nitrofluoren-9-ylidene)methyl]aniline:

**Higher polarity of solvent generally increases solubility** in polar solvents.
**Increased size and sterics in the compound** may decrease solubility in water.

Understanding these solubility behaviors can guide effective applications and techniques for utilizing this compound in various chemical processes.

Interesting facts

Facts About N,N-dimethyl-4-[(2-nitrofluoren-9-ylidene)methyl]aniline

N,N-dimethyl-4-[(2-nitrofluoren-9-ylidene)methyl]aniline is a fascinating compound that blends intriguing structural features with valuable applications. Here are some noteworthy facts about this compound:

Complex Structure: This compound features both an aniline moiety and a nitrofluorene unit, offering a unique combination of properties often explored in organic synthesis and materials science.
Optoelectronic Applications: Due to its structural features, it holds promise in optoelectronic devices. The presence of conjugated systems can enhance properties such as light absorption and emission, making it suitable for use in organic light-emitting diodes (OLEDs) and photovoltaic cells.
Research Interest: The compound has garnered attention in research due to its potential in developing new light-absorbing materials. Its ability to act as a dye can be useful in organic solar cells and photocatalysis.
Versatility: N,N-dimethyl-4-[(2-nitrofluoren-9-ylidene)methyl]aniline can be modified through various synthetic pathways, allowing chemists to explore derivatives with tailored functionalities for specific applications.
Toxicity Considerations: As with many nitro compounds, safety precautions are warranted when handling N,N-dimethyl-4-[(2-nitrofluoren-9-ylidene)methyl]aniline. Nitro groups are known to potentially enhance the toxicity profile of compounds, necessitating careful risk assessments in laboratory and industrial settings.

In summary, N,N-dimethyl-4-[(2-nitrofluoren-9-ylidene)methyl]aniline represents a bridge between chemistry, material science, and technology, showcasing how complex organic molecules can lead to innovative advancements in various fields.