34677-78-6

Basic information

• Product Name: 4-{4-[bis(2-hydroxyethyl)amino]phenyl}butanoic acid
• CAS NO: 34677-78-6
• Molecular Formula: C₁₄H₂₁NO₄
• Molecular Weight: 267.3208
• Mol File: 34677-78-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 503.1°C at 760 mmHg
• Flash Point: 258.1°C
• Density: 1.238g/cm³
• Vapor Pressure: 6.07E-11mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: 4-{4-[bis(2-hydroxyethyl)amino]phenyl}butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-{4-[bis(2-hydroxyethyl)amino]phenyl}butanoic acid(34677-78-6)
• EPA Substance Registry System: 4-{4-[bis(2-hydroxyethyl)amino]phenyl}butanoic acid(34677-78-6)

Safety Data

• Hazardous Substances Data: 34677-78-6(Hazardous Substances Data)

Upstream product

• 305-03-3 chlorambucil 
• 302-04-5 Thiocyanate 
• 27171-89-7 4-butyric acid 

Relevant articles and documents

Role of thiocyanate ion in detoxification of the anticancer agent chlorambucil

N,N-Bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil, 1) is an orally administrated drug widely used in the chemotherapy of chronic lymphocytic leukemia. We have recently described a new metabolic path for the decomposition of 1 in human gastric juice based on its reactions with saliva- derived thiocyanate ion. We report here our quantitative data on the reactions of thiocyanate ion with CLB in various fluid matrixes at 37 °C. The rate of decomposition of 1 is zero-order with respect to SCN- concentration up to 100 mM. However, thiocyanate ion reacts ca. 18 300 times faster than water with the aziridinium ion derived from I at neutral and acidic pH. When the SCN- concentration was greater than 10 mM, practically no N,N-bis(2-hydroxyethyl)-p-aminophenylbutyric acid, 4, the product of chlorambucil hydrolysis, could be detected. Thiocyanate ion also effectively overcompensates for the rate retardation caused by Cl-; 10 mM SCN- is enough to decrease the effect of 0.5 M chloride ion to one-half. This is an important factor in human gastric juice where the chloride ion concentration is normally high.

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.

Potential Errors in Kinetic Studies of Hydrolysis of Nitrogen Mustards Based on Chloride-Ion Determination

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