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Amino dibromo anthraquinone

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Identification
Molecular formula
C14H6Br2NO2
CAS number
81-49-2
IUPAC name
1-amino-2,4-dibromo-anthracene-9,10-dione
State
State

The compound is a solid at room temperature. Due to its molecular structure, it is relatively stable and typically does not sublimate or degrade easily under typical conditions.

Melting point (Celsius)
282.00
Melting point (Kelvin)
555.00
Boiling point (Celsius)
465.00
Boiling point (Kelvin)
738.00
General information
Molecular weight
388.91g/mol
Molar mass
388.9100g/mol
Density
3.0000g/cm3
Appearence

1-Amino-2,4-dibromo-anthracene-9,10-dione appears as a dark, crystalline solid. The compound is typically bright in color, often reflecting shades of red or orange due to the conjugated systems in the anthraquinone structure, which absorb and reflect visible light.

Comment on solubility

Solubility of 1-amino-2,4-dibromo-anthracene-9,10-dione

The solubility of 1-amino-2,4-dibromo-anthracene-9,10-dione can be influenced by several factors, including the presence of bromine substituents and the amino group, which affect its interaction with solvents. In general, this compound tends to be sparingly soluble in polar solvents due to its large aromatic system. However, it may show improved solubility in solvents such as:

  • Dimethyl sulfoxide (DMSO)
  • Dimethylformamide (DMF)
  • Chloroform

When evaluating solubility, it’s essential to consider the following points:

  1. Influence of Polarity: The amino group can introduce slight polarity, aiding solubility in polar solvents.
  2. Hydrophobic Interactions: The bromine atoms contribute to hydrophobic character, potentially reducing solubility in water.
  3. Temperature Dependence: Solubility often increases with temperature; hence, heating the solvent may enhance dissolution.

In summary, while 1-amino-2,4-dibromo-anthracene-9,10-dione exhibits limited solubility in water, using aprotic solvents or heating can facilitate its dissolution, expanding its usability in various chemical applications.

Interesting facts

Interesting Facts about 1-Amino-2,4-dibromo-anthracene-9,10-dione

1-amino-2,4-dibromo-anthracene-9,10-dione is a fascinating compound with various intriguing characteristics and applications:

  • Structure and Functionality: This compound is a derivative of anthracene, which is a polycyclic aromatic hydrocarbon (PAH) known for its multiple fused benzene rings. The unique substitution of amino and bromo groups enhances its chemical reactivity and functional properties.
  • Chemical Reactivity: The presence of the amino group makes this compound an effective participant in various organic reactions, including nucleophilic substitutions and coupling reactions, making it a valuable building block in synthetic chemistry.
  • Color and Luminescence: Compounds like 1-amino-2,4-dibromo-anthracene-9,10-dione often exhibit vivid colors and can display photoluminescent properties. This is particularly interesting in dye applications and in the development of organic light-emitting diodes (OLEDs).
  • Biological Significance: Some derivatives of anthracene are studied for their biological activity, including potential anti-cancer properties. The bromination and amination could enhance interactions with biological targets, which is an area of ongoing research.
  • Material Science Applications: Its unique properties have garnered interest in the field of material science, especially in the development of conductive polymers and organic semiconductors.

As one researcher put it, "Compounds like 1-amino-2,4-dibromo-anthracene-9,10-dione not only showcase the beauty of chemistry but also remind us of the potential applications in technology and medicine."

In summary, the multifaceted nature of 1-amino-2,4-dibromo-anthracene-9,10-dione makes it a compound worthy of study in various scientific fields, including organic chemistry, material science, and pharmacology.

Synonyms
1-AMINO-2,4-DIBROMOANTHRAQUINONE
81-49-2
Dibromoaminoanthraquinone
1-amino-2,4-dibromoanthracene-9,10-dione
2,4-Dibromo-1-anthraquinonylamine
9,10-Anthracenedione, 1-amino-2,4-dibromo-
1-Amino-2,4-dibromanthrachinon
Anthraquinone, 1-amino-2,4-dibromo-
NCI-C55458
NSC 3529
CCRIS 5884
HSDB 5241
RF75O3IKOZ
1-Amino-2,4-dibromo-anthraquinone
EINECS 201-354-0
BRN 1993373
1-Amino-2,4-dibromanthrachinon [Czech]
DTXSID4039235
AI3-16445
NSC-3529
DTXCID9052
1-amino-2,4-dibromo-9,10-anthraquinone
1-Amino-2,4-dibromoanthra-9,10-quinone
CHEBI:82304
NSC3529
4-14-00-00444 (Beilstein Handbook Reference)
1-AMINO-2,4-DIBROMOANTHRAQUINONE [IARC]
1-amino-2,4-dibromo-9,10-dihydroanthracene-9,10-dione
1-Amino-2,4-dibromanthrachinon (Czech)
ADBAQ
1-AMINO-2,4-DIBROMOANTHRAQUINONE (IARC)
UNII-RF75O3IKOZ
NSC 3529; 1-Amino-2,4-dibromo-9,10-anthracenedione; 1-Amino-2,4-dibromo-9,10-anthraquinone; 1-Amino-2,4-dibromoanthraquinone; 2,4-Dibromo-1-anthraquinonylamine
MFCD00019155
1-amino-2,4-dibromo-9,10-Anthracenedione
Anthraquinone,4-dibromo-
1Amino2,4dibromanthrachinon
2,4Dibromo1anthraquinonylamine
9, 1-amino-2,4-dibromo-
CHEMBL559749
SCHEMBL3272427
Anthraquinone, 1amino2,4dibromo
l-amino-2,4-dibromoanthraquinone
1-Amino-2, 4-dibromoanthraquinone
Tox21_202582
BBL013158
STK803590
AKOS000668885
9,10Anthracenedione, 1amino2,4dibromo
CAS-81-49-2
NCGC00260131-01
WLN: L C666 BV IVJ DZ EE GE
AC-13906
AS-61164
CI-55458
1-AMINO-2,4-DIBROMOANTHRA-QUINONE
DB-056532
CS-0188511
NS00038127
C19211
E76133
AE-641/00127034
9,10-ANTHRACENEDIONE,1-AMINO-2,4-DIBROMO-
Q27155867
201-354-0