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Mitoxantrone

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Identification
Molecular formula
C22H28Cl2N4O6
CAS number
65271-80-9
IUPAC name
2-[[4-[bis(2-chloroethyl)amino]phenyl]methylene]propanedinitrile
State
State

Mitoxantrone is typically in a solid state at room temperature, however, in medical usage, it is often found in liquid form as a solution ready for intravenous injection.

Melting point (Celsius)
211.00
Melting point (Kelvin)
484.20
Boiling point (Celsius)
453.50
Boiling point (Kelvin)
726.60
General information
Molecular weight
421.30g/mol
Molar mass
444.1530g/mol
Density
1.3974g/cm3
Appearence

Mitoxantrone appears as a dark blue or blue-black crystalline solid. It is often available as a solution for injection and has a characteristic dark coloration due to its chemical structure.

Comment on solubility

Solubility of 2-[[4-[bis(2-chloroethyl)amino]phenyl]methylene]propanedinitrile

The solubility of 2-[[4-[bis(2-chloroethyl)amino]phenyl]methylene]propanedinitrile is quite intriguing and can be influenced by several factors. This compound exhibits varying solubility in different solvents due to its complex structure, which includes both hydrophobic and hydrophilic components. Here are some key points regarding its solubility:

  • Polar Solvents: It may show limited solubility in highly polar solvents like water, due to the presence of large alkyl groups which hinder interaction with water molecules.
  • Non-Polar Solvents: In contrast, it tends to be more soluble in non-polar organic solvents such as chloroform or benzene, where its aromatic and aliphatic portions can interact favorably.
  • Concentration Effects: At higher concentrations, the solubility may change due to intermolecular interactions leading to aggregation, which can reduce effective solubility in a given solvent.
  • Temperature Dependence: The solubility is also temperature-dependent; typically, increasing the temperature enhances solubility for many organic compounds.

As a general rule, the phrase “like dissolves like” can often elucidate the solubility behavior of this compound. In essence, understanding the solubility characteristics of 2-[[4-[bis(2-chloroethyl)amino]phenyl]methylene]propanedinitrile is critical for its applications in different chemical environments.

Interesting facts

Interesting Facts about 2-[[4-[bis(2-chloroethyl)amino]phenyl]methylene]propanedinitrile

This compound is a significant member of the chemical family known for its unique reactivity and potential applications in medicinal chemistry. Below are some intriguing insights regarding this complex molecule:

  • Anticancer Potential: Compounds like this one are often studied for their potential as anticancer agents. The presence of chlorinated amines can enhance the potency of drugs targeting cancer cells.
  • Mechanism of Action: The structure suggests that it could act through alkylation mechanisms, which can damage DNA and hinder replication in rapidly dividing cells, a hallmark of cancer treatment.
  • Structure-Activity Relationship (SAR): The intricate design of the molecule allows chemists to hypothesize about how modifications in the chemical structure can lead to increased efficacy or reduced side effects, paving the way for more targeted therapies.
  • Synthetic Routes: The synthesis of this compound often involves multiple steps of organic reactions, showcasing the creativity and problem-solving skills of synthetic chemists. Exploring various synthetic routes is essential for efficient large-scale production.
  • Potential Side Effects: Like many pharmaceuticals, compounds with similar structures have been noted for their potential side effects, including toxicity issues. Therefore, extensive studies are mandatory before any therapeutic application.
  • Research Applications: In addition to medicinal chemistry, this compound may be useful in academic research, particularly in exploring new drug delivery systems due to its complex nature.

In summary, 2-[[4-[bis(2-chloroethyl)amino]phenyl]methylene]propanedinitrile stands out not only for its complex molecular structure but also for its promising role in the field of pharmacology and chemical research. Its multifaceted applications make it a captivating subject for chemists and researchers alike.

Synonyms
Malononitrile mustard
4213-30-3
NSC-48841
UM 951
p-Bis(2-chloroethyl)aminobenzilidine malononitrile
AI3-50194
MALONONITRILE, p-(BIS(2-CHLOROETHYL)AMINO)BENZYLIDENE
Malononitrile, (p-(bis(2-chloroethyl)amino)benzylidene)-
p-(Bis-(beta-chloroethyl)-amino)benzylidene malononitrile
Propanedinitrile, ((4-(bis(2-chloroethyl)amino)phenyl)methylene)-
Propanedinitrile, [[4-[bis(2-chloroethyl)amino]phenyl]methylene]-
Malononitrile, p-[bis(2-chloroethyl)amino]benzylidene
BRN 2987923
Malononitrile, (p-[bis(2-chloroethyl)amino]benzylidene)-
2-[[4-[bis(2-chloroethyl)amino]phenyl]methylidene]propanedinitrile
J98WA78ELK
CHEMBL169232
WLN: NCYCN&U1R DN2G2G
DTXSID70194965
NSC48841
NSC801423
Propanedinitrite, ((4-(bis(2-chloroethyl)amino)phenyl)methylene)-
NSC-801423
4-[Bis(2-chloroethyl)amino]benzylidenemalononitrile
p-[Bis(.beta.-chloroethyl)amino]benzylidene malononitrile