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Chlorambucil

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Identification
Molecular formula
C14H19Cl2NO2
CAS number
305-03-3
IUPAC name
3-[bis(2-chloroethyl)amino]-4-ethyl-benzoic acid
State
State

At room temperature, chlorambucil is a solid. Generally, it comes in the form of tablets when used for medicinal purposes.

Melting point (Celsius)
65.00
Melting point (Kelvin)
338.15
Boiling point (Celsius)
270.80
Boiling point (Kelvin)
543.90
General information
Molecular weight
304.21g/mol
Molar mass
304.2140g/mol
Density
1.3255g/cm3
Appearence

Chlorambucil is a pale yellow solid at room temperature. It may present as a fine powder and has a tendency to be hygroscopic, meaning it can absorb moisture from the surroundings.

Comment on solubility

Solubility of 3-[bis(2-chloroethyl)amino]-4-ethyl-benzoic acid

The solubility of 3-[bis(2-chloroethyl)amino]-4-ethyl-benzoic acid in various solvents can provide insights into its potential applications and behavior in different environments. Here are some key aspects to consider regarding its solubility:

  • Polar Solvents: This compound is expected to exhibit moderate to high solubility in polar solvents due to its carboxylic acid group, which can engage in hydrogen bonding.
  • Apolar Solvents: In contrast, solubility in non-polar solvents may be limited due to the presence of polar functional groups.
  • pH Dependence: The solubility profile might also change significantly with pH, particularly because the carboxylic acid can be deprotonated at higher pH, which could enhance solubility in aqueous solutions.
  • Effect of Substituents: The chlorinated side chain can influence the overall hydrophobicity of the molecule, potentially impacting its solubility characteristics.

In summary, understanding the solubility of this compound requires an appreciation of the interplay between its functional groups and the solvent environment. As always, theoretical predictions should be substantiated with empirical data to confirm solubility behavior across varying conditions.

Interesting facts

Interesting Facts About 3-[bis(2-chloroethyl)amino]-4-ethyl-benzoic acid

3-[bis(2-chloroethyl)amino]-4-ethyl-benzoic acid is a fascinating compound known for its significant applications in medicinal chemistry, especially in the development of anticancer agents. Here are some engaging insights about this intriguing chemical:

  • Mechanism of Action: This compound acts primarily as a DNA alkylating agent. By forming covalent bonds with DNA, it can interfere with the replication process, which is crucial in inhibiting the growth of cancer cells.
  • Historical Importance: The development of compounds like 3-[bis(2-chloroethyl)amino]-4-ethyl-benzoic acid has been essential in the evolution of cancer therapies since the mid-20th century.
  • Structure-Activity Relationship (SAR): The presence of the ethyl group and the bis(2-chloroethyl)amino moiety enhances the compound's lipophilicity, which is vital for its ability to penetrate cellular membranes and exert its pharmacological effects.
  • Drug Design: Compounds derived from this structure are often modified to improve their efficacy and reduce side effects. This highlights the importance of structural variations in drug discovery.
  • Toxicity Considerations: While effective against tumors, such compounds can also affect normal cells, leading to side effects such as nausea and bone marrow suppression, highlighting the need for careful dosing and monitoring.

In summary, 3-[bis(2-chloroethyl)amino]-4-ethyl-benzoic acid stands out not only for its chemical structure but also for its role in the ongoing fight against cancer, exemplifying the delicate balance between efficacy and safety in drug development.

Synonyms
BRN 2752425
BENZOIC ACID, 3-(BIS(2-CHLOROETHYL)AMINO)-4-ETHYL-
5977-03-7
DTXSID10208499
3-(Bis(2-chloroethyl)amino)-4-ethylbenzoic acid
DTXCID80130990