6-Chlorouracil (CAS Number: 4270-27-3) is a halogenated pyrimidine derivative often used in biochemical research as an enzyme inhibitor and a building block in organic synthesis, particularly for creating heterocyclic mesomeric betaines. It commonly appears as a white to off-white powder.
Properties
CAS Number: 4270-27-3
Molecular Weight: 146.53 g/mol
Melting Point: 290–295°C (decomposition)
Appearance: White to off-white powder
Solubility: Soluble in Ammonium Hydroxide
Density: 1.61±0.1 g/cm³ (predicted)
Storage: Store at 2-8°C, preferably in a dark, sealed place
Synonyms
6-Chloropyrimidine-2,4(1H,3H)-dione
6-Chloro-2,4-dihydroxypyrimidine
2,4-Pyrimidinediol, 6-chloro-
6-chloro-1H-pyrimidine-2,4-dione
NSC 43265
NSC 210419
Uses and Applications
Biochemical Research: It functions as an inhibitor of yeast alcohol dehydrogenase (ADH-H) and a potential inhibitor of DNA repair glycosylases.
Organic Synthesis: Used in the synthesis of heterocyclic systems, such as converting it into pyridinium-substituted uracils (mesomeric betaines) by reacting with pyridine derivatives.
Nucleic Acid Studies: Useful for investigating the impact of halogenation on nucleic acid base-pair stability and alkali metal ion affinity.
Pharmaceutical Intermediates: Employed as a reactant for developing novel compounds in pharmaceutical research.
Analytical Chemistry: Employed as a reagent and standard in chemical research.
Synthesis
6-Chlorouracil is generally synthesized from 2,4,6-trichloropyrimidine via a controlled hydrolysis process with sodium hydroxide (NaOH) under refluxing conditions, followed by acidification to produce a high yield (around 97%) of 6-chlorouracil.