20295-24-3

Basic information

• Product Name: 5-ETHYL-6-CHLOROURACIL
• Synonyms: 5-ETHYL-6-CHLOROURACIL;6-CHLORO-5-ETHYLURACIL;6-chloro-5-ethyldihydropyrimidine-2,4(1H,3H)-dione
• CAS NO: 20295-24-3
• Molecular Formula: C₆H₇ClN₂O₂
• Molecular Weight: 174.58
• Mol File: 20295-24-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.41g/cm³
• Refractive Index: 1.552
• CAS DataBase Reference: 5-ETHYL-6-CHLOROURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ETHYL-6-CHLOROURACIL(20295-24-3)
• EPA Substance Registry System: 5-ETHYL-6-CHLOROURACIL(20295-24-3)

Safety Data

• Hazardous Substances Data: 20295-24-3(Hazardous Substances Data)

Usage

General Description

5-Ethyl-6-Chlorouracil is a chemical compound with the molecular formula C6H7ClN2O2. It is an analog of uracil, containing an additional ethyl group at the 5th position and a chlorine atom at the 6th position. 5-ETHYL-6-CHLOROURACIL is primarily used as a building block in the synthesis of various pharmaceuticals and agrochemicals. It has been studied for its potential antitumor and antiviral properties, showing promise as a potential therapeutic agent. Additionally, 5-Ethyl-6-Chlorouracil is also used in research and studies related to the uracil derivatives and their biological activities. Overall, this chemical compound has potential applications in the pharmaceutical and agrochemical industries due to its unique structure and potential biological activities.

InChI:InChI=1/C6H7ClN2O2/c1-2-3-4(7)8-6(11)9-5(3)10/h2H2,1H3,(H2,8,9,10,11)

Upstream product

• 120268-44-2 5-ethyl-6-chloro-2,4-dimethoxypyrimidine 
• 133-13-1 ethyl diethyl malonate 
• 1780-38-7 2,4,6-trichloro-5-ethylpyrimidine 
• 2518-72-1 5-ethyl barbituric acid 

Downstream Products

• 100763-60-8 6-Benzylamino-5-ethyl-1H-pyrimidine-2,4-dione 
• 172256-32-5 1-Benzyloxymethyl-6-chloro-5-ethyl-1H-pyrimidine-2,4-dione 
• 152433-65-3 6-phenylthio-5-ethyuracil 
• 171048-61-6 5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 
• 1310053-25-8 6-[4-(2-methoxyphenyl)-1-piperazinyl]-5-ethyluracil 
• 1310053-24-7 6-(4-phenyl-1-piperazinyl)-5-ethyluracil 
• 172256-05-2 1-[(benzyloxy)methyl]-6-[(3,5-dimethylphenyl)selenenyl]-5-ethyluracil 
• 172256-02-9 6-(3,5-Dimethyl-phenylselanyl)-1-ethoxymethyl-5-ethyl-1H-pyrimidine-2,4-dione 
• 155831-53-1 1-<(benzyloxy)methyl>-5-ethyl-6-(phenylselenenyl)uracil 
• 867038-75-3 1-[(benzyloxy)methyl]-5-ethyl-6-(1-nitro-2-naphthylthio)uracil 
• 867038-78-6 1-[(benzyloxy)methyl]-5-ethyl-6-(1-amino-2-naphthylthio)uracil 
• 100763-64-2 5-Ethyl-6-p-tolylamino-1H-pyrimidine-2,4-dione 

Relevant articles and documents

Synthesis and antimicrobial activity of some novel 5-alkyl-6-substituted uracils and related derivatives

6-Chloro-5-ethyl-, n-propyl- and isopropyluracils 5a-c were efficiently prepared from the corresponding 5-alkybarbituric acids 3a-c via treatment with phosphorus oxychloride and N,N-dimethylaniline to yield the corresponding 5-alkyl-2,4,6-trichloropyrimidines 4a-c, which were selectively hydrolyzed by heating in 10% aqueous sodium hydroxide for 30 minutes. The reaction of compounds 5a-c with 1-substituted piperazines yielded the corresponding 5-alkyl-6-(4-substituted-1-piperazinyl)uracils 6a-j. The target 8-alkyltetrazolo[1,5-f]pyrimidine-5,7(3H,6H)-diones 7a-c were prepared via the reaction of 5a-c with sodium azide. Compounds 6a-j and 7a-c were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compound 6h displayed potent broad-spectrum antibacterial activity, while compound 6b showed moderate activity against the Gram-positive bacteria. All the tested compounds were practically inactive against Candida albicans.

Synthesis of certain 6-(arylthio)uracils as potential antiviral agents

A series of 6-(Arylthio)uracils have been prepared via condensation of 6-chlorouracil or 5-ethyl-6-chlorouracil with the corresponding thiopnenol derivatives in pyridine or ethanolic potassium hydroxide. The synthesized compounds were tested for their antiviral activity. Some of the 5-ethyl-6-(arylthio)uracil derivatives 10a-g showed moderate activities against hepatitis B Virus (HBV) and HIV-1 virus.

A New Route to the Improved Synthesis of 1-(Alkoxymethyl)-5-alkyl- 6-(arylselenenyl)uracils

A new route to C-6-selenenyl analogs of compound 1a from 5-alkyl-6-chlorouracils 6a-b has been described. A mild and highly efficient synthesis of 1-(alkoxymethyl)-5-alkyl-6-(arylselenenyl)uracils 8a-e has been accomplished from 6a-b in good yields using a two step procedure. Silylation of 5-alkyl-6-chlorouracils 6a-b using N,O-bis(trimethylsilyl)acetamide followed by regioselective alkylation of the silylated intermediate with ethyl or benzyl chloromethyl ether in dichloromethane afforded the desired 1-(alkoxymethyl)-5-alkyl-6-chlorouracils 7a-d in 88-94% yields. Compounds 7a-d readily underwent addition-elimination reaction with an appropriate arylselenol in the presence of ethanolic sodium hyroxide to produce the corresponding 1-(alkoxymethyl)-5-alkyl-6-(arylselenenyl)uracils 8a-e in excellent yields (94-99%).