1953-33-9

Basic information

• Product Name: 5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione
• Synonyms: 5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione;5-n-Butylbarbituric acid;5-Butylbarbituric acid;5-Butyl-2,4,6(1H,3H,5H)-pyrimidinetrione;5-butyl-1,3-diazinane-2,4,6-trione
• CAS NO: 1953-33-9
• Molecular Formula: C₈H₁₂N₂O₃
• Molecular Weight: 184.19248
• EINECS: 217-781-0
• Mol File: 1953-33-9.mol

Chemical Properties

• Appearance: /
• Density: 1.161 g/cm³
• Refractive Index: 1.468
• CAS DataBase Reference: 5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione(1953-33-9)
• EPA Substance Registry System: 5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione(1953-33-9)

Safety Data

• Hazardous Substances Data: 1953-33-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione is utilized as an intermediate in the synthesis of drugs targeting the central nervous system. Its unique structure allows it to interact with specific receptors and pathways, making it a valuable component in the development of medications for neurological disorders.
Used in Neurological Disorder Treatment:
In the field of neurology, 5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione is studied for its potential therapeutic effects on various neurological disorders. Its ability to modulate specific neural pathways and receptors may contribute to the management or treatment of these conditions.
Used as an Anticonvulsant:
5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione has been researched for its potential as an anticonvulsant, a medication used to prevent or reduce the frequency of seizures in individuals with epilepsy. Its mechanism of action may involve stabilizing neuronal membranes and reducing the excitability of the nervous system.
Used in Pest Control:
5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione has also been investigated for its insecticidal properties, suggesting that it could be used in pest control applications to manage and eliminate harmful insect populations. This could be particularly useful in agricultural settings to protect crops from damage.
Used as a Potential Herbicide:
5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione has been researched for its potential as a herbicide, indicating that it may be effective in controlling the growth of unwanted plants. This could be beneficial in agricultural and horticultural applications to maintain the health and productivity of cultivated areas.
However, it is important to note that the potential toxicity and environmental impact of 5-butyl-1H,3H,5H-pyrimidine-2,4,6-trione need to be thoroughly evaluated before it can be widely adopted in these applications. Further research is necessary to understand its safety profile and long-term effects on ecosystems and human health.

InChI:InChI=1/C8H12N2O3/c1-2-3-4-5-6(11)9-8(13)10-7(5)12/h5H,2-4H2,1H3,(H2,9,10,11,12,13)

Upstream product

• 67-52-7 BARBITURIC ACID 
• 123-72-8 butyraldehyde 
• 133-08-4 diethyl butylmalonate 
• 57-13-6 urea 
• 64-17-5 ethanol 
• 79835-86-2 5-bromo-5-butyl-pyrimidine-2,4,6-trione 
• 58713-10-3 5-butyryl-pyrimidine-2,4,6-trione 
• 123-73-9 crotonaldehyde 

Downstream Products

• 67526-22-1 5-but-2-enyl-5-butyl-barbituric acid 
• 3146-66-5 5-n-Butyl-5-allylbarbitursaeure 
• 67050-53-7 5-butyl-5-[1]naphthylmethyl-barbituric acid 
• 14095-64-8 5-butyl-2,4,6-trichloro-pyrimidine 
• 67050-81-1 5-Butyl-5-vinyl-barbitursaeure 
• 99097-09-3 Benzoic acid (2R,3R,4S,5R)-3-acetoxy-5-(5-butyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-tetrahydro-furan-2-ylmethyl ester 
• 5442-52-4 5-butyluracil 

Relevant articles and documents

Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates

Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate. If 5-benzylbarbiturate is the target product, then the first step includes the preparation of 5-benzylidene. Regardless of the nature of the first step, all reactions presented synthetic yields around 90% and isolation and purification involves only crystallization.

Convergent functional groups. 10. Molecular recognition of neutral substrates

In this paper synthetic molecular clefts with functional groups complementary to adenines, diketopiperazines, and barbiturates are described. Lactams and imides are compared for hydrogen-bonding affinites toward each other and to the heterocycles mentioned above. Titrations in CDCl3 using NMR show association constants vary by factors of 104 for adenines, 102 for diketopiperazines, and 10 for barbiturates with the new receptors. Enantioselective recognition of cyclo-L-Leu-Leu is observed, corresponding to ΔΔG = 2.7 kcal/mol. The relative strengths of hydrogen-bonding arrays are interpreted in terms of secondary interactions such as defined in the following paper in this issue by Jorgensen and Severance.

Reduction of Isopropylidene Acylmalonates, 5-Acylbarbituric Acids, and 3-Acyl-4-hydroxycoumarins to the Corresponding Alkyl Derivatives by Sodium Cyanoborohydride-Acetic Acid

Isopropylidene acylmalonates, 5-acylbarbituric acids, and 3-acyl-4-hydroxycoumarins are readily reduced to the corresponding alkyl derivatives by sodium cyanoborohydride-acetic acid.The cyclic substrates are readily prepared by the acylation of isopropylidene malonate, barbituric acid (or its N,N'-dimethyl derivative), and 4-hydroxycoumarin, according to procedures developed by other workers.The reductions take place upon addition of a 2 mol equiv of sodium cyanoborohydride to a mixture of the acyl compound and acetic acid.This reductive transformation completes a synthetic method for the preparation of the alkyl derivatives starting from the parent compound.