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Sulfur mustard

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Identification
Molecular formula
C4H8Cl2S
CAS number
Mustard gas does not have a CAS number because it is a chemical warfare agent with limited legitimate use.
IUPAC name
2-amino-3-[[4-[bis(2-chloroethyl)amino]phenyl]methylsulfonyl]propanoic acid
State
State

Sulfur mustard exists as a liquid at room temperature, exhibiting a viscous and oily texture. It is not a gas under standard conditions despite the common name 'mustard gas.'

Melting point (Celsius)
14.40
Melting point (Kelvin)
287.55
Boiling point (Celsius)
217.00
Boiling point (Kelvin)
490.15
General information
Molecular weight
159.08g/mol
Molar mass
159.0800g/mol
Density
1.2695g/cm3
Appearence

Sulfur mustard is typically observed as a colorless, viscous liquid at room temperature. However, depending on the conditions or impurities, it can appear as a yellow to brown liquid. It is also well-known for its pungent odor resembling that of mustard plants, garlic, or horseradish, which is why it has been infamously called mustard gas, despite being a liquid.

Comment on solubility

Solubility of 2-amino-3-[[4-[bis(2-chloroethyl)amino]phenyl]methylsulfonyl]propanoic acid

The solubility of 2-amino-3-[[4-[bis(2-chloroethyl)amino]phenyl]methylsulfonyl]propanoic acid is influenced by several key factors, making it an interesting compound to analyze. Typically, the presence of both amino and sulfonyl groups enhances the potential for solubility in polar solvents such as water. However, certain characteristics must be considered:

  • Polar Functional Groups: The amino group (-NH2) and sulfonyl group (-SO2) are known for their ability to form hydrogen bonds, which can increase solubility.
  • Hydrophobic Regions: The bis(2-chloroethyl)amino moiety contributes hydrophobic characteristics, which may limit solubility in polar solvents.
  • pH Dependency: The acidity of the carboxylic acid group may also play a crucial role in solubility. At lower pH, the carboxylic acid can remain protonated, while at higher pH, it can ionize, impacting solubility.

In general, while the compound may show some degree of solubility in aqueous solutions, it is important to conclude that its overall solubility will likely be moderate due to the competing hydrophobic and hydrophilic interactions. Thus, it is often essential to explore specific solubilizing agents or conditions to enhance its solubility profile:

  • Buffer solutions to control pH
  • Co-solvents to improve compatibility

As a result, understanding the solubility behavior of this compound is critical for its application in pharmaceuticals, especially considering its complex structure. "Solubility profiles can significantly influence the efficacy and delivery of therapeutic agents."

Interesting facts

Interesting Facts about 2-amino-3-[[4-[bis(2-chloroethyl)amino]phenyl]methylsulfonyl]propanoic acid

2-amino-3-[[4-[bis(2-chloroethyl)amino]phenyl]methylsulfonyl]propanoic acid, often referred to as a derivative of amino acids, possesses several intriguing characteristics that make it notable in the field of medicinal chemistry.

1. Structural Complexity

This compound features a multi-functional structure that includes:

  • Amino group - essential for forming peptide bonds.
  • Sulfonyl group - significant in bioactivity and drug development.
  • Bis(2-chloroethyl)amino group - known for its use in chemotherapy agents.

2. Role in Anti-Cancer Drug Development

The incorporation of a bis(2-chloroethyl)amino moiety ties this compound to the realm of cytotoxic agents. This structural element is a hallmark of alkylating agents, which are widely utilized in the treatment of various cancers. As a result:

  • This compound could act against tumor growth.
  • It serves as a scaffold for designing novel therapeutic agents.

3. Importance in Biological Studies

As a hybrid molecule, its interactions can be studied in various biological systems. Biochemists and pharmacologists are particularly interested in:

  • Understanding its mechanism of action at the molecular level.
  • Investigating potential effects on cellular processes such as apoptosis.

4. Potential Side Effects

While promising, the use of compounds like 2-amino-3-[[4-[bis(2-chloroethyl)amino]phenyl]methylsulfonyl]propanoic acid comes with concerns, including:

  • Cytotoxicity - affecting not only cancer cells but also non-cancerous cells.
  • Potential for drug resistance in tumors, complicating treatment regimens.

Conclusion

Overall, 2-amino-3-[[4-[bis(2-chloroethyl)amino]phenyl]methylsulfonyl]propanoic acid is not just a simple compound but a fascinating entity with implications for drug design, therapeutic applications, and the study of biological mechanisms. Its complexity underscores the intricate relationship between chemical structures and biological functions.

Synonyms
3-(p-(Bis(2-chloroethyl)amino)benzylsulfonyl)-L-alanine
6940-98-3
L-Alanine, 3-(((4-(bis(2-chloroethyl)amino)phenyl)methyl)sulfonyl)-
L-Alanine, 3-[[[4-[bis(2-chloroethyl)amino]phenyl]methyl]sulfonyl]-
NSC 60431
3-[p-[Bis(2-chloroethyl)amino]benzylsulfonyl]-L-alanine
BRN 2821420
NSC60431
3-p-Bis(2-chloroethyl)amino benzylsulfonyl-L-alanine
ALANINE, beta-(p-(BIS(2-CHLOROETHYL)AMINO)BENZYLSULFONYL)-, L-
NSC-60431
WLN: QVYZ1SW1R DN2G2G -L