511-67-1

Usage

Uses

Used in Pharmaceutical Industry:
5,5-Dibromobarbituric acid is used as a chemical intermediate for the synthesis of condensed pteridine systems. It undergoes condensation with 4,5-diamino-pyrimidines in the presence of pyridine, which is crucial for the development of new pharmaceutical compounds with potential therapeutic applications. This process allows for the creation of novel molecules that can be further explored for their medicinal properties and efficacy in treating various health conditions.

InChI:InChI=1/C4H2Br2N2O3/c5-4(6)1(9)7-3(11)8-2(4)10/h(H2,7,8,9,10,11)

Upstream product

• 67-52-7 BARBITURIC ACID 
• 87-39-8 violuric acid 
• 476-61-9 [5,5']bipyrimidinyl-2,4,6,2',4',6'-hexaone 
• 67-56-1 methanol 
• 27402-47-7 5-benzylidenebarbituric acid 
• 7726-95-6 bromine 
• 7732-18-5 water 
• 19645-78-4 5-bromobarbituric acid 
• 56032-78-1 2,4,6-trioxo-hexahydro-pyrimidine-5-carboxylic acid amide 
• 480-68-2 dilituric acid 
• 62459-19-2 5,5-dibromo-6-hydroxy-6-methyl-5,6-dihydrouracil 
• 7697-37-2 nitric acid 
• 58713-02-3 5-acetyl-pyrimidine-2,4,6-trione 
• 65-86-1 orotic acid 

Downstream Products

• 5807-13-6 1,3,6,8-tetrahydro-2,4,5,7-pyrimido<5,4-g>pteridinetetrone 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 19645-78-4 5-bromobarbituric acid 
• 24618-31-3 bromo-1 methoxy-2 cyclohexane 
• 99845-54-2 N-phenyl-N'-(2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-thiourea 
• 67-52-7 BARBITURIC ACID 
• 444-15-5 5-hydroxybarbituric acid 
• 76-24-4 Alloxantin 
• 506-68-3 bromocyane 
• 75-25-2 Bromoform 
• 88982-70-1 tribromoacetyl-urea 

Relevant academic research and scientific papers

5-Bromobarbituric acid : A mild and selective monobrominating agent employed in the synthesis of the gastrin antagonist GR174152

5-Bromobarbituric acid (5) is a convenient reagent for the selective bromination of cyclic imine 3. A facile, in situ synthesis of this reagent involving a disproportionation reaction between barbituric acid and dibromobarbituric acid is described.

Identification of Inhibitors of Cholesterol Transport Proteins Through the Synthesis of a Diverse, Sterol-Inspired Compound Collection

Cholesterol transport proteins regulate a vast array of cellular processes including lipid metabolism, vesicular and non-vesicular trafficking, organelle contact sites, and autophagy. Despite their undoubted importance, the identification of selective modulators of this class of proteins has been challenging due to the structural similarities in the cholesterol-binding site. Herein we report a general strategy for the identification of selective inhibitors of cholesterol transport proteins via the synthesis of a diverse sterol-inspired compound collection. Fusion of a primary sterol fragment to an array of secondary privileged scaffolds led to the identification of potent and selective inhibitors of the cholesterol transport protein Aster-C, which displayed a surprising preference for the unnatural-sterol AB-ring stereochemistry and new inhibitors of Aster-A. We propose that this strategy can and should be applied to any therapeutically relevant sterol-binding protein.

C-S and C-N coupling reactions of barbituric acid via selective and complete bromination using greener KBr/H2O2 as a brominating agent

1,3-Disubstituted/unsubstituted barbituric acids on treatment with KBr-H2O2 as a greener brominating reagent give mono and dibromo barbituric acids. With aqueous HCl selective bromination and without aqueous HCl complete bromination of active methylene group of barbituric acids took place. The reaction of monobarbituric acids with thiosemicarbazide and thioglyoxalic acid under refluxing in aqueous medium, simple C-S coupling products were obtained.The spiro C-N coupling product was obtained by the interaction of dibromo barbituric acid with thiosemicarbazide and C-N condensation product was obtained by the interaction of dibromo barbituric acid with guanidine nitrate, both reactions took place in aqueous medium under refluxing conditions. An environmentally benign, aqueous mediated C-S and C-N organic transformation by the interaction of barbituric acids mediated by KBr-H2O2 as a greener brominating reagent is described. The simple product workup, use of inexpensive greener reagent KBr-H2O2 for bromination and simple purification without column are the additional advantages of synthetic protocol.

Solvent-free bromination reactions with sodium bromide and oxone promoted by mechanical milling

New solvent-free brominations of 1,3-dicarbonyl compounds, phenols, various alkenes including chalcones, azachalcones, 4-phenylbut-3-en-2-one, methyl cinnamate, styrene and 1,3-cyclohexadiene were efficiently achieved by employing sodium bromide and oxone under mechanical milling conditions. The brominated products were obtained in good to excellent yields.

Conversion of nucleophilic halides to electrophilic halides: Efficient and selective halogenation of azinones, amides, and carbonyl compounds using metal halide/lead tetraacetate

AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc) 4 are efficient electrophilic N- and α-C-halogenating agents. A variety of azinones, amides and carbonyl compounds were chemoselectively and regioselectively N-, or α-C-halogenated in good to excellent yield using AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc)4 in acetonitrile. Georg Thieme Verlag Stuttgart.

Synthesis of novel galactopyranosyl-derived spiro barbiturates

Malonic acid undergoes condensation readily with ureas to yield barbituric acids 2, which on bromination give 5,5-dibromobarbituric acids 3. Reaction of α-D-galactose with these 5,5-dibromo barbituric acids afforded 2,3-α-D-galactopyrano-1,4-dioxo-7,9-diaza-spiro[4,5]deca-6,8,10-triones 4. The structures of the products have been assigned on the basis of 1H NMR, 13C NMR, FAB-MS, optical activity, and elemental analysis. The title compounds are found to have antibacterial and antifungal activities.

5,5-Dibromobarbituric Acid, a Convenient New Reagent for the Bromination of Saturated and α,β-Unsaturated Carbonyl Compounds

5,5-Dibromobarbituric acid (1) was used for the bromination of saturated and α,β-unsaturated aldehydes and keto compounds.