Skip to main content

Chlorambucil

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

Chlorambucil is typically found as a solid at room temperature. It is stable under normal conditions of use and storage but should be kept away from excessive heat and moisture.

Melting point (Celsius)
65.00
Melting point (Kelvin)
338.15
Boiling point (Celsius)
315.00
Boiling point (Kelvin)
588.15
General information
Molecular weight
304.20g/mol
Molar mass
304.2010g/mol
Density
1.2740g/cm3
Appearence

Chlorambucil appears as a white to pale yellow crystalline powder. It is odorless and has a slightly bitter taste. It is sensitive to light and should be stored in a dark container to prevent degradation.

Comment on solubility

Solubility of 2-[4-[bis(2-chloroethyl)amino]phenyl]acetic acid (C14H19Cl2NO2)

The solubility of 2-[4-[bis(2-chloroethyl)amino]phenyl]acetic acid is influenced by its chemical structure and functional groups. This compound exhibits characteristics that affect its interaction with solvents:

  • Polarity: The presence of the bis(2-chloroethyl)amino group increases polarity, which may enhance solubility in polar solvents like water.
  • Hydrophilic vs. Hydrophobic Balance: The phenyl group introduces a hydrophobic character, which can decrease solubility in water.
  • pH Dependence: As an acid, solubility may vary with pH; it may become more soluble in alkaline conditions where it can ionize.
  • Solvent Sensitivity: Increased solubility in organic solvents such as ethanol or DMSO may be observed due to its molecular structure.

Overall, the solubility is a complex interplay of these factors, leading to variable solubility profiles. Examining these characteristics is vital for applications in pharmacology and material science. As noted in the literature, "the solubility of such compounds can greatly influence their bioavailability and effectiveness."

Interesting facts

Interesting Facts about 2-[4-[bis(2-chloroethyl)amino]phenyl]acetic acid

2-[4-[bis(2-chloroethyl)amino]phenyl]acetic acid is a fascinating compound in the field of medicinal chemistry, showing potential in various therapeutic applications. Here are some compelling insights about this intriguing molecule:

  • Historical Context: The compound is part of a class of drugs known as alkylating agents, which were first developed in the mid-20th century. This class of drugs was pivotal in revolutionizing cancer treatment.
  • Mechanism of Action: The compound operates by forming covalent bonds with DNA, leading to the disruption of cell replication. This characteristic makes it particularly effective in targeting rapidly dividing cancer cells.
  • Therapeutic Uses: Its primary applications include the treatment of certain types of cancers, particularly lymphomas and leukemias. Understanding its medicinal properties provides insight into how chemical modifications can enhance efficacy and reduce toxicity.
  • Research Implications: Ongoing research is focused on investigating the pharmacokinetics and pharmacodynamics of this compound. Such studies are critical to developing new analogs and improving the selectivity and safety profiles of cancer therapies.
  • Structure–Activity Relationship (SAR): The unique structure of this compound allows scientists to explore how alterations in the molecular framework can influence its activity. This exploration is crucial for drug design and optimization.

In summary, 2-[4-[bis(2-chloroethyl)amino]phenyl]acetic acid exemplifies the intricate relationship between chemical structure and biological activity. Its contributions to cancer therapy highlight the importance of chemistry in advancing medical science.

Synonyms
Phenacid
10477-72-2
Chlorphenacyl
Khlorfenatsil
N,N-Bis(2-chloroethyl)-p-aminophenylacetic acid
NSC 71964
p-N,N-(Dichloroethyl)aminophenylacetic acid
N,N-Bis(chloroethyl)-p-aminophenylacetic acid
UNII-32842A3UZP
CB 1331
BRN 0960062
32842A3UZP
4-(Bis(2-chloroethyl)amino)benzeneacetic acid
(p-(Bis(2-chloroethyl)amino)phenyl)acetic acid
NSC-71964
(4-(Bis(2-chloroethyl)amino)phenyl)acetic acid
p-(N,N-Di(2-chloroethyl)amino)phenylacetic acid
p-N,N-Di-(2-chloroethyl)aminophenyl acetic acid
2-(p-(Bis(2-chloroethyl)amino)phenyl)acetic acid
Acetic acid, (p-(bis(2-chloroethyl)amino)phenyl)-
DTXSID40146714
4-14-00-01313 (Beilstein Handbook Reference)
ACETIC ACID, 2-(p-(BIS(2-CHLOROETHYL)AMINO)PHENYL)-
PHENYLACETIC ACID MUSTARD (0.25%)
4-[Bis(2-chloroethyl)amino]benzeneacetic Acid
4-(N,N-bis(2-chloroethyl)amino)phenylacetic acid
(P-BIS(2-CHLOROETHYL)AMINOPHENYL)ACETIC ACID
Acetic acid, [p-[bis(2-chloroethyl)amino]phenyl]-
BIS(2-CHLOROETHYL)AMINOBENZENEACETIC ACID, 4-
[p-[Bis(2-chloroethyl)amino]phenyl]acetic acid
[4-[Bis(2-chloroethyl)amino]phenyl]acetic acid
p-[N,N-Di(2-chloroethyl)amino]phenylacetic acid
2-[p-[Bis(2-chloroethyl)amino]phenyl]acetic acid
4-[N,N-Bis(2-chloroethyl)amino]phenylacetic acid
p-(N,N-bis(2-chloroethyl)amino)phenylacetic acid
DTXCID5069205
Acetic acid, (p-(bis(2-chloroethyl)amino)phenyl)-(8CI)
Phenylacetic acid mustard
Chlorphenacil
Phenylacetic mustard
PAAM
2-{4-[di(2-chloroethyl)amino]phenyl}acetic acid
2-[4-[bis(2-chloroethyl)amino]phenyl]acetic acid
Benzeneacetic acid, 4-[bis(2-chloroethyl)amino]-
Benzeneacetic acid, 4-(bis(2-chloroethyl)amino)-
2-(4-(bis(2-chloroethyl)amino)phenyl)acetic acid
2-{4-[bis(2-chloroethyl)amino]phenyl}acetic acid
CHEMBL518
NCIOpen2_003741
SCHEMBL7468547
RQAFMLCWWGDNLI-UHFFFAOYSA-N
NSC71964
AKOS000588971
DA-76814
HY-136327
CS-0128229
ST50233633
p-[di-(2-chloroethyl)amino]phenylacetic acid
SR-01000313749
4-BIS(2-CHLOROETHYL)AMINOBENZENEACETIC ACID
SR-01000313749-1
Q27256160
Phenylacetic Mustard; Benzeneacetic acid, 4-[bis(2-chloroethyl)amino]- (9CI, ACI); 4-[Bis(2-chloroethyl)amino]benzeneacetic acid (ACI); Acetic acid, [p-[bis(2-chloroethyl)amino]phenyl]- (6CI, 8CI); 2-[p-[Bis(2-chloroethyl)amino]phenyl]acetic acid; 4-[N,N-Bis(2-chloroethyl)amin