2518-72-1

Basic information

• Product Name: 5-ethylbarbituric acid
• Synonyms: 5-ethylbarbituric acid;5-Ethylpyrimidine-2,4,6(1H,3H,5H)-trione;5-ethyl-1,3-diazinane-2,4,6-trione
• CAS NO: 2518-72-1
• Molecular Formula: C₆H₈N₂O₃
• Molecular Weight: 156.13932
• EINECS: 219-743-9
• Mol File: 2518-72-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 225-226 °C
• Appearance: /
• Density: 1.243 g/cm³
• Refractive Index: 1.467
• PKA: 4.62±0.40(Predicted)
• CAS DataBase Reference: 5-ethylbarbituric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ethylbarbituric acid(2518-72-1)
• EPA Substance Registry System: 5-ethylbarbituric acid(2518-72-1)

Safety Data

• Hazardous Substances Data: 2518-72-1(Hazardous Substances Data)

Usage

General Description

5-ethylbarbituric acid, also known as ethallobarbital, is a chemical compound belonging to the class of barbiturates. It is a derivative of barbituric acid and is used as a hypnotic and sedative medication. This chemical works by binding to the GABA-A receptors in the brain, leading to an increase in the inhibitory neurotransmission, thereby causing sedation and relaxation. It has a similar chemical structure to other barbiturates and has similar effects, including reducing anxiety, inducing sleep, and suppressing the central nervous system. 5-ethylbarbituric acid is considered to be a controlled substance due to its potential for abuse and addiction, and is therefore strictly regulated in many countries.

InChI:InChI=1/C6H8N2O3/c1-2-3-4(9)7-6(11)8-5(3)10/h3H,2H2,1H3,(H2,7,8,9,10,11)

Upstream product

• 67-52-7 BARBITURIC ACID 
• 75-07-0 acetaldehyde 
• 24867-19-4 5-ethyl-pyrimidine-2,4,6-triamine 
• 6082-49-1 ethyl propanediamide 
• 105-58-8 Diethyl carbonate 
• 76-74-4 pentobarbital 
• 64-17-5 ethanol 
• 58713-02-3 5-acetyl-pyrimidine-2,4,6-trione 
• 5750-82-3 5-bromo-5-ethyl-pyrimidine-2,4,6-trione 
• 5750-81-2 5-chloro-5-ethyl-pyrimidine-2,4,6-trione 
• 7664-93-9 sulfuric acid 
• 10035-10-6 hydrogen bromide 
• 75016-38-5 vinbarbital 
• 76-76-6 probarbital 

Downstream Products

• 15302-82-6 5-Aethyl-5-(β-hydroxy-β-phenylaethyl)-barbitursaeure 
• 41333-97-5 4-(5-ethyl-2,4,6-trioxo-hexahydro-pyrimidin-5-ylazo)-N-thiazol-2-yl-benzenesulfonamide 
• 41334-02-5 4-(5-ethyl-2,4,6-trioxo-hexahydro-pyrimidin-5-ylazo)-N-(4-methyl-thiazol-2-yl)-benzenesulfonamide 
• 41371-06-6 N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-4-(5-ethyl-2,4,6-trioxo-hexahydro-pyrimidin-5-ylazo)-benzenesulfonamide 
• 57-44-3 diethylbarbituric acid 
• 4212-49-1 5-ethyluracil 
• 854840-82-7 5-ethyl-5-(5-hydroxymethyl-2-methyl-5-nitro-[1,3]dioxan-2-ylmethyl)-barbituric acid 
• 171048-68-3 (3,5-dimethylphenyl)(5-ethyl-2,6-dimethoxypyrimidin-4-yl)methanone 
• 1304033-83-7 6-benzoyl-1-(benzyloxymethyl)-5-ethyl-3-hydroxypyrimidine-2,4(1H,3H)-dione 
• 1304033-84-8 6-benzoyl-5-ethyl-1-((4-fluorobenzyloxy)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione 
• 1304033-86-0 6-(3,5-dimethylbenzoyl)-5-ethyl-1-((4-fluorobenzyloxy)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione 
• 1304033-87-1 1-(benzyloxymethyl)-6-(3,5-dimethylbenzoyl)-5-ethyl-3-hydroxypyrimidine-2,4(1H,3H)-dione 
• 1304033-88-2 6-benzoyl-5-ethyl-1-((4-fluorophenethoxy)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione 
• 1304033-89-3 6-(3,5-dimethylbenzoyl)-5-ethyl-1-((4-fluorophenethoxy)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione 

Relevant articles and documents

Synthesis and acid- and base-catalyzed reactions of hexobarbital 1',2'-epoxide and heptabarbital 1',2'-epoxide

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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.

Non-nucleoside HIV-1 reverse transcriptase inhibitors, part 7. Synthesis, antiviral activity, and 3D-QSAR investigations of novel 6-(1-naphthoyl) HEPT analogues

A series of novel 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) analogues bearing a 6-(1-naphthoyl) group of non-nucleoside human immunodeficiency virus (HIV) reverse transcriptase inhibitors were synthesized and evaluated for their activity against HIV-1 and HIV-2. It was found that most of these compounds showed good activity against HIV-1. Among them, compound 5-isopropyl-6-(1-naphthoyl)-1-[(2E)-3-phenylallyl]-2,4-pyrimidinedione (23) displayed the greatest inhibitory potency (IC50=0.14 μM), which is about 35-fold more active than HEPT and DDI. To rationalize the relationships between structure and activity of these novel compounds, a three-dimensional quantitative structure-activity relationship (3D-QSAR) model was also generated. The results provided a tool for guiding the further design of more potent antiviral agents and for predicting the affinity of related compounds.