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9-Aminoantracene

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Identification
Molecular formula
C14H11N
CAS number
26380-72-9
IUPAC name
anthracen-9-amine
State
State

At room temperature, 9-Aminoantracene is in a solid state. It is typically found in the form of crystalline flakes.

Melting point (Celsius)
252.00
Melting point (Kelvin)
525.15
Boiling point (Celsius)
410.00
Boiling point (Kelvin)
683.15
General information
Molecular weight
193.25g/mol
Molar mass
193.2500g/mol
Density
1.1200g/cm3
Appearence

9-Aminoantracene appears as yellow to greenish-yellow crystalline solid. This compound can sometimes show fluorescence under ultraviolet or extended visible light exposure.

Comment on solubility

Solubility of Anthracen-9-amine

Anthracen-9-amine, with the chemical formula C14H11N, exhibits unique solubility characteristics due to its aromatic hydrocarbon structure combined with an amine group. Understanding its solubility behavior is essential for various applications, especially in organic synthesis and materials science.

Solubility Characteristics

The solubility of anthracen-9-amine can be influenced by several factors, including:

  • Polarity: The presence of the amine group renders the molecule somewhat polar, which enhances its solubility in polar solvents.
  • Temperature: Increased temperatures can improve solubility in many solvents, facilitating the process of dissolution.
  • Solvent Type: Anthracen-9-amine is generally more soluble in organic solvents such as:
    • Dimethyl sulfoxide (DMSO)
    • Acetone
    • Tetrahydrofuran (THF)
  • Complexation: In some cases, anthracen-9-amine can form complexes with metal ions or other reagents, which may alter its solubility profile.

However, it is worth noting that anthracen-9-amine has limited solubility in water, aligning with the general trend observed in many polycyclic aromatic amines. As a result, the solubility properties can be summarized as:

  • High solubility in organic solvents.
  • Low solubility in water.

In conclusion, while anthracen-9-amine presents interesting solubility characteristics in organic solvents, its lower solubility in water can pose challenges depending on the desired applications. Understanding these nuances is vital for effectively harnessing its properties in practical uses.

Interesting facts

Interesting Facts about Anthracen-9-amine

Anthracen-9-amine, a fascinating derivative of anthracene, is a compound that has attracted considerable interest in various fields of chemistry and materials science. Here are some intriguing aspects of this compound:

Properties and Applications

  • Versatile Building Block: Anthracen-9-amine serves as a crucial building block in organic synthesis, making it essential for the production of more complex molecules.
  • Fluorescent Properties: This compound exhibits notable fluorescent properties, which contribute to its value in optoelectronic devices and in the development of fluorescent probes for biological applications.
  • Energy Transfer: Anthracen-9-amine is known to be efficient in energy transfer processes in molecular systems, which has implications in dye-sensitized solar cells and light-emitting devices.

Biological Significance

  • Potential Therapeutic Uses: Anthracen-9-amine has shown promise in medical research, particularly in the development of anti-cancer agents due to its ability to intercalate DNA.
  • Drug Development: Its amine functional group can form various derivatives that may enhance the solubility and bioactivity of pharmaceutical compounds.

Chemical Behavior

As a member of the polycyclic aromatic amines, anthracen-9-amine's unique structural configuration contributes to its reactivity patterns:

  • Nucleophilic Reactions: The amino group allows for nucleophilic substitutions, making it a versatile site for chemical reactions.
  • Stacking Interactions: The planar structure of anthracene provides strong π-π stacking interactions, which play a crucial role in the physical properties of solid-state materials.

In summary, anthracen-9-amine is not only significant in the realm of organic chemistry but also holds potential in advanced applications ranging from materials science to drug development. As stated by chemists in the field, "Its structural attributes open up a myriad of innovative pathways for exploration and application." This compound truly exemplifies the intersection of chemistry and technological advancement.

Synonyms
9-Aminoanthracene
anthracen-9-amine
779-03-3
9-ANTHRAMINE
5-Aminoanthracene
CCRIS 7001
E3EA4FE3SX
NSC 125517
BRN 2209405
CHEBI:50472
NSC-125517
DTXSID60228526
4-12-00-03437 (Beilstein Handbook Reference)
DTXCID10151017
811-778-3
inchi=1/c14h11n/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9h,15h
lhniceldcmppde-uhfffaoysa-n
9-Anthracenamine
9-anthrylamine
10-Anthracylamine
9-aminoanthracen
10-Anthracylamine; 5-Aminoanthracene; 9-Aminoanthracene; NSC 125517; NSC 155202
Anthracen-9-Ylamine
MFCD00452690
anthracen-9-yl-amine
UNII-E3EA4FE3SX
YSWG602
CHEMBL82266
SCHEMBL1264430
NSC125517
AKOS015854634
AS-56568
DB-022276
A1748
CS-0169911
T71332
Q27122085