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Anthralin

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Identification
Molecular formula
C14H10O4
CAS number
1143-38-0
IUPAC name
1-hydroxy-2-(hydroxymethyl)anthracene-9,10-dione
State
State
Solid at room temperature.
Melting point (Celsius)
168.00
Melting point (Kelvin)
441.15
Boiling point (Celsius)
645.00
Boiling point (Kelvin)
918.15
General information
Molecular weight
226.23g/mol
Molar mass
226.2270g/mol
Density
1.4250g/cm3
Appearence

Anthralin appears as a yellow to orange-brown crystalline powder. It can be colorless when freshly prepared but turns brown upon exposure to air and light due to oxidation.

Comment on solubility

Solubility of 1-hydroxy-2-(hydroxymethyl)anthracene-9,10-dione

The solubility of 1-hydroxy-2-(hydroxymethyl)anthracene-9,10-dione in various solvents can be characterized by several key aspects:

  • Polar Solvents: This compound exhibits moderate solubility in polar solvents such as water and alcohols due to its hydroxyl groups that can form hydrogen bonds.
  • Aromatic Solvents: It generally shows better solubility in non-polar or weakly polar aromatic solvents, reflecting the hydrophobic nature of the anthracene structure.
  • pH Dependency: The solubility may be influenced by the pH of the solution, with increased solubility observed in basic conditions due to deprotonation of the hydroxyl group, which enhances solvation.
  • Temperature Effects: Higher temperatures usually result in increased solubility for many solid compounds, including this anthracene derivative, due to greater molecular motion.

In summary, the solubility profile of 1-hydroxy-2-(hydroxymethyl)anthracene-9,10-dione reflects a balance between its polar functional groups and its hydrophobic aromatic backbone. Understanding these solubility characteristics is crucial for applications in various fields, including organic chemistry and material sciences.

Interesting facts

Interesting Facts about 1-Hydroxy-2-(hydroxymethyl)anthracene-9,10-dione

1-Hydroxy-2-(hydroxymethyl)anthracene-9,10-dione, often referred to in scientific literature as an anthraquinone derivative, is a compound of significant interest in various fields, including organic chemistry and materials science. This compound is notable for its unique structural features and functional properties.

Key Characteristics

  • Versatile Applications: This compound serves as an important intermediate in the synthesis of dyes, pigments, and pharmaceuticals. Its ability to undergo various chemical transformations makes it highly useful in organic synthesis.
  • Fluorescent Properties: One remarkable feature of this compound is its potential for fluorescence. This property is valuable in applications such as fluorescent probes in biological systems, allowing scientists to visualize and track biological processes.
  • Role in Photovoltaics: With the growing interest in renewable energy, 1-hydroxy-2-(hydroxymethyl)anthracene-9,10-dione finds its way into research related to organic solar cells. Its unique electronic properties contribute to the efficiency of these devices.
  • Biological Activity: Compounds of the anthraquinone family, including this one, have been studied for their potential antimicrobial and anticancer activities. This makes them of interest in medicinal chemistry and drug discovery.

Historical Perspective

The anthraquinone scaffold has a rich history in organic chemistry dating back to the early studies of organic compounds. As noted by renowned chemist Sir William H. Perkin, “The study of anthraquinones has opened up vast avenues for exploration in both chemistry and biology.”

In summary, 1-hydroxy-2-(hydroxymethyl)anthracene-9,10-dione is not only a compound of chemical interest but also a gateway to advancements in fields ranging from materials science to pharmaceuticals. Researchers continue to explore its potential, unlocking new applications and understanding its behavior in various environments.

Synonyms
Digiferruginol
24094-45-9
Digiferrugineol
1-hydroxy-2-(hydroxymethyl)anthracene-9,10-dione
1-Hydroxy-2-(hydroxymethyl)-9,10-anthracenedione
DTXSID40178818
1-hydroxy-2-(hydroxymethyl)anthraquinone
RefChem:907617
DTXCID00101309
Deoxylucidin
1-Hydroxy-2-hydroxymethylanthraquinone
BRN 2218948
ANTHRAQUINONE, 1-HYDROXY-2-HYDROXYMETHYL-
9,10-Anthracenedione, 1-hydroxy-2-(hydroxymethyl)-
CHEBI:4544
4-08-00-03278 (Beilstein Handbook Reference)
CHEMBL495276
orb1991526
SCHEMBL23199057
SCHEMBL30614617
JCZCSQSSSAHDCB-UHFFFAOYSA-N
AKOS040735238
FS-7792
G89236
1-Hydroxy-2-(hydroxymethyl)anthra-9,10-quinone #
Q27106407
1-HYDROXY-2-(HYDROXYMETHYL)-9,10-DIHYDROANTHRACENE-9,10-DIONE