27171-89-7

Basic information

• Product Name: 4-{4-[(2-chloroethyl)(2-hydroxyethyl)amino]phenyl}butanoic acid
• CAS NO: 27171-89-7
• Molecular Formula: C₁₄H₂₀ClNO₃
• Molecular Weight: 285.7665
• Mol File: 27171-89-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 480.3°C at 760 mmHg
• Flash Point: 244.3°C
• Density: 1.243g/cm³
• Vapor Pressure: 4.89E-10mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: 4-{4-[(2-chloroethyl)(2-hydroxyethyl)amino]phenyl}butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-{4-[(2-chloroethyl)(2-hydroxyethyl)amino]phenyl}butanoic acid(27171-89-7)
• EPA Substance Registry System: 4-{4-[(2-chloroethyl)(2-hydroxyethyl)amino]phenyl}butanoic acid(27171-89-7)

Safety Data

• Hazardous Substances Data: 27171-89-7(Hazardous Substances Data)

Usage

General Description

The chemical 4-{4-[(2-chloroethyl)(2-hydroxyethyl)amino]phenyl}butanoic acid, also known as chlorambucil, is a nitrogen mustard alkylating agent that is widely used in the treatment of certain types of cancer, including lymphoma, leukemia, and ovarian cancer. It works by attaching to DNA and interfering with its replication, ultimately leading to the death of cancer cells. Chlorambucil is an oral medication that is typically taken once a day. It is known to have common side effects such as nausea, vomiting, and suppression of bone marrow function, and is associated with an increased risk of developing secondary cancers. Despite its potential side effects, chlorambucil is an important and effective treatment option for many cancer patients.

Upstream product

• 305-03-3 chlorambucil 
• 20637-09-6 methyl 4-(4-aminophenyl)butanoate 

Downstream Products

• 34677-78-6 4-phenyl>butyric acid 

Relevant articles and documents

Kinetics of chlorambucil hydrolysis using high-pressure liquid chromatography

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Preparation method of chlorambucil derivative

The invention discloses a preparation method of a chlorambucil derivative. The method comprises the steps that 4-(4-aminophenyl)butanoic acid methyl ester serves as the starting material, and the chlorambucil derivative is synthesized through six-step reactions. The optimal preparation steps and reaction conditions are screened out by means of a large number of experiments, the whole process is reasonable in design and high in operability, and purification is convenient. According to the prepared chlorambucil derivative, the purity can reach 99% or above, and the total yield can reach 50% or above. The prepared chlorambucil derivative can be widely applied to experiments for comprehensively analyzing pharmacology, pharmacologic metabolism, toxicology and the like of chlorambucil.

Mechanism and reactivity of chlorambucil and chlorambucil-spermidine conjugate

The mechanism and kinetics of hydrolysis of chlorambucil and chlorambucil-spermidine conjugate in aqueous buffered solutions have been compared.In the absence of added chloride ion the reactions are shown to be first-order in the nitrogen mustard and independent of the nucleophile concentration.In the presence of high concentrations of sodium chloride the reaction is reversible and is subject to a significant common-ion effect.The rates of hydrolysis of both compounds are independent of pH in the range 8 to 3.5, and both rates begin to drop rapidly below pH 3.5 which corresponds to the pKas of the aryl amine groups.The relative rates of alkylation of a range nucleophiles by chlorambucil have been deduced from the isokinetic points, and have shown that the phosphate dianion, imidazole base and particularly thiolates are all capable of competing with water for the aziridinium ion at comparatively low concentrations.The rates of reaction of chlorambucil and chlorambucil-spermidine conjugate have been shown to be sensitive to the medium, and, in particular, there is a large micellar inhibition of the hydrolysis of chlorambucil (60-fold reduction in rate) in the presence of hexadecyltrimethylammonium chloride that is not seen for the conjugate.These data are all accounted for in terms of a rate limiting formation of the aziridinium ion intermediate in each case.No evidence for any other mechanistic pathways was found.