Skip to main content

Mechlorethamine

ADVERTISEMENT
Identification
Molecular formula
C5H11Cl2N
CAS number
51-75-2
IUPAC name
N,N-bis(2-chloroethyl)propan-2-amine
State
State

At room temperature, mechlorethamine is typically in a liquid state. It is often supplied and stored as a hydrochloride salt in a solid form to ensure stability and manage its reactivity and corrosive nature.

Melting point (Celsius)
-20.00
Melting point (Kelvin)
253.15
Boiling point (Celsius)
145.00
Boiling point (Kelvin)
418.15
General information
Molecular weight
156.07g/mol
Molar mass
156.0660g/mol
Density
1.0630g/cm3
Appearence

Mechlorethamine appears as a colorless to pale yellow liquid. It is oily in nature and possesses a faint fishy or musty odor. The compound is highly reactive and is sensitive to light and moisture, which can lead to decomposition. Due to its chemical reactivity, it is often handled in solution form.

Comment on solubility

Solubility of N,N-bis(2-chloroethyl)propan-2-amine

N,N-bis(2-chloroethyl)propan-2-amine, also known as bis(2-chloroethyl)amine derivative, is an intriguing compound with specific solubility characteristics.

When considering the solubility of this compound, several key points emerge:

  • Polar Nature: The chloroethyl groups impart a degree of polarity, enhancing solubility in polar solvents.
  • Solvent Compatibility: It is generally more soluble in organic solvents such as methanol and ethanol compared to non-polar solvents.
  • Water Solubility: Water solubility is limited due to the hydrophobic characteristics of the alkyl chains, though some degree of interaction may occur due to the amine functional group.
  • Temperature Influence: Like many organic compounds, increased temperature can facilitate higher solubility levels in various solvents.

In summary, while N,N-bis(2-chloroethyl)propan-2-amine exhibits some solubility in polar solvents, it is best characterized as moderately soluble. The unique structure and substituent interactions significantly influence its solubility profile.

Interesting facts

Interesting Facts about N,N-bis(2-chloroethyl)propan-2-amine

N,N-bis(2-chloroethyl)propan-2-amine, commonly known as a nitrogen mustard derivative, is a fascinating compound with both historical and modern significance in the field of chemistry and medicine.

1. Chemical Structure and Mechanism

This compound belongs to a class of compounds known as alkylating agents, which react with DNA, potentially leading to cell death. The mechanism involves the formation of reactive cyclic intermediates that can alkylate DNA, thereby disrupting cellular processes.

2. Medicinal Applications

N,N-bis(2-chloroethyl)propan-2-amine has been investigated for its antitumor properties. It has been used in the development of chemotherapeutic agents due to its ability to target rapidly dividing cancer cells. Some key applications include:

  • Treatment of various cancers
  • Research in drug development
  • Tool for studying cancer biology

3. Historical Significance

This compound and its derivatives gained prominence during World War II, both for the development of chemical warfare agents and their later adaptation into cancer treatments. The dual nature of its use highlights the ethical complexities within chemical research.

4. Safety and Handling

Due to its potential toxicity and harmful effects, N,N-bis(2-chloroethyl)propan-2-amine requires careful handling in laboratory settings. Researchers often emphasize the importance of:

  • Utilizing protective equipment
  • Adhering to safety protocols
  • Being aware of its mutagenic properties

5. Future Perspectives

As research progresses, there is an ongoing effort to modify the structure of nitrogen mustards to improve efficacy while reducing side effects, such as toxicity to healthy cells. The future may hold new and exciting developments in:

  • Targeted therapy
  • Combination treatments
  • Improved drug delivery systems

In summary, N,N-bis(2-chloroethyl)propan-2-amine serves as a crucial intersection of chemistry, medicine, and ethics, making it a compelling subject of study for both chemists and medical professionals alike.

Synonyms
619-34-1
Triethylamine, 2',2''-dichloro-1-methyl-
DTXSID60210926
RefChem:1100392
DTXCID90133417
Isopropyl-S
2-Propanamine, N,N-bis(2-chloroethyl)-
TL-301
NIOSH/YE1578000
Isopropyl-bis(beta-chloroethyl)amine
2,2'-Dichloro-1''-methyltriethylamine
Triethylamine, 2,2'-dichloro-1''-methyl-
YE15780000
TL 301
N,N-bis(2-chloroethyl)propan-2-amine
2',2''-Dichloro-1-methyltriethylamine
BRN 1737075
4-04-00-00509 (Beilstein Handbook Reference)
SCHEMBL6566774
bis(2-chloroethyl)(methylethyl)amine
isopropyl-bis(beta-chloroethyl) amine
propane, 2-bis(2-chloroethyl)amino-
ST45026181