Description

5-Chlorouracil (CAS No. 1820-81-1) is a halogenated pyrimidine derivative with the molecular formula C₄H₃ClN₂O₂ and IUPAC name 5-chloro-1H-pyrimidine-2,4-dione. This white to off-white crystalline solid is a key intermediate in organic synthesis and pharmaceutical research, particularly in the development of nucleoside analogs and antimetabolites. With a molecular weight of 146.53 g/mol, 5-Chlorouracil exhibits high purity (>98%) and is soluble in polar solvents such as DMSO and water under controlled conditions. Its chlorinated uracil structure makes it a valuable precursor for modified nucleobases used in biochemical studies, antiviral agents, and anticancer drug discovery. Proper storage at 2-8°C in a tightly sealed container is recommended to ensure stability.

Properties

• CAS Number: 1820-81-1
• Complexity: 199
• IUPAC Name: 5-chloro-1H-pyrimidine-2,4-dione
• InChI: InChI=1S/C4H3ClN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
• InChI Key: ZFTBZKVVGZNMJR-UHFFFAOYSA-N
• Exact Mass: 145.9883050
• Molecular Formula: C4H3ClN2O2
• Molecular Weight: 146.53
• SMILES: C1=C(C(=O)NC(=O)N1)Cl
• Topological: 58.2
• Monoisotopic Mass: 145.9883050
• Synonyms: 5-CHLOROURACIL, 1820-81-1, 2,4(1H,3H)-Pyrimidinedione, 5-chloro-, 5-chloropyrimidine-2,4(1H,3H)-dione, 5-Chloro-2,4-dihydroxypyrimidine, Uracil, 5-chloro-, CHEBI:60762, EINECS 217-339-7, 7LQ4V03RNY, NSC 28172, AI3-26560, NSC-28172, CHLOROURACIL, 5-, 5-chloro-2,4-pyrimidinedione, DTXSID7075137, FLUOROURACIL IMPURITY E [EP IMPURITY], FLUOROURACIL IMPURITY E (EP IMPURITY), Uracil, 5-chloro-(VAN), DTXCID6035788, Uracil, 5-chloro-(VAN) (8CI), 217-339-7, inchi=1/c4h3cln2o2/c5-2-1-6-4(9)7-3(2)8/h1h,(h2,6,7,8,9, 5-Chloro-1H-pyrimidine-2,4-dione, 5-chloro-uracil, MFCD00006019, 164415-64-9, 4(3H)-Pyrimidinone, 5-chloro-2-hydroxy- (9CI), 2,4-Pyrimidinediol, 5-chloro- (9CI), NSC28172, 107577-08-2, 210369-56-5, 5-Chlorouracil (Fluorouracil Impurity), 5-Chloropyrimidine-2,4(1H,3H)-dione (5-Chlorouracil), 5-chloro-1,3-dihydropyrimidine-2,4-dione, UNII-7LQ4V03RNY, Uracil, 5-chloro- (VAN), Fluorouracil Impurity E, Epitope ID:138111, SCHEMBL42227, SCHEMBL67366, SCHEMBL440392, SCHEMBL440393, CHEMBL144082, SCHEMBL11004342, SCHEMBL29163681, HY-I0959, 2,3H)-Pyrimidinedione, 5-chloro-, SBB004103, AKOS003093906, AKOS003242135, AKOS006222774, AC-8694, FC05961, SB57723, 5-Chlorouracil, ReagentPlus(R), 99%, AS-10925, NCI60_002298, PD121670, SY028182, 5-Chloro-2,4(1H,3H)-pyrimidinedione #, DB-029133, DB-268951, DB-272208, pyrimidine-2,4(1H,3H)-dione, 5-chloro-, CS-0010970, NS00045646, ST45025452, EN300-96343, 2(1H)-Pyrimidinone,5-chloro-4-hydroxy-(9ci), 5-Chlorouracil, Vetec(TM) reagent grade, 98%, 2(1H)-PYRIMIDINONE, 5-CHLORO-4-HYDROXY-, 4(3H)-PYRIMIDINONE, 5-CHLORO-2-HYDROXY-, Q238482, 5-chloro-1,2,3,4-tetrahydropyrimidine-2,4-dione, Z1203730752, 5UC

Application

5-Chlorouracil serves as a critical building block in medicinal chemistry for synthesizing modified nucleosides with potential antiviral and antitumor activity. Researchers utilize this compound to study DNA/RNA interactions and enzyme inhibition mechanisms due to its ability to mimic natural pyrimidines. In pharmaceutical development, it’s employed as a precursor for fluorouracil analogs and other chemotherapeutic agents targeting thymidylate synthase.

Safety and Hazards

GHS Hazard Statements

• H301 (75%): Toxic if swallowed [Danger Acute toxicity, oral]
• H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]
• H341 (75%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

Precautionary Statements

• P203, P264, P270, P280, P301+P316, P301+P317, P318, P321, P330, P405, and P501

Hazard Classes and Categories

• Acute Tox. 3 (75%)
• Muta. 2 (75%)

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