511-67-1

Basic information

• Product Name: 5,5-DIBROMOBARBITURIC ACID
• Synonyms: 5,5-DIBROMOBARBITURIC ACID;Barbituric acid, 5,5-dibromo-;5,5-Dibromohexahydropyrimidine-2,4,6-trione;5,5-Dibromopyrimidine-2,4,6(1H,3H,5H)-trione;Dibromin;5,5-Dibromo-2,4,6(1H,3H,5H)-pyrimidinetrione;5,5-dibromo-1,3-diazinane-2,4,6-trione;5,5-Di BroMo Barbutyric Acid
• CAS NO: 511-67-1
• Molecular Formula: C₄H₂Br₂N₂O₃
• Molecular Weight: 285.88
• EINECS: 208-131-7
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks
• Mol File: 511-67-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 240-242 °C(lit.)
• Appearance: /
• Density: 2.5685 (rough estimate)
• Refractive Index: 1.6220 (estimate)
• PKA: pKa 5.68±0.02(H2O t=25.0±0.02 I=0.00)(Approximate)
• CAS DataBase Reference: 5,5-DIBROMOBARBITURIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-DIBROMOBARBITURIC ACID(511-67-1)
• EPA Substance Registry System: 5,5-DIBROMOBARBITURIC ACID(511-67-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 511-67-1(Hazardous Substances Data)

Usage

Uses

5,5-Dibromobarbituric acid was used in the synthesis of condensed pteridine system by undergoing condensation with 4,5-diamino-pyrimidines in the presence of pyridine.

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

• 87-39-8 violuric acid 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 91135-71-6 5-benzoyl-pyrimidine-2,4,6-trione 
• 476-61-9 [5,5']bipyrimidinyl-2,4,6,2',4',6'-hexaone 
• 65-86-1 orotic acid 
• 58713-02-3 5-acetyl-pyrimidine-2,4,6-trione 
• 62459-19-2 5,5-dibromo-6-hydroxy-6-methyl-5,6-dihydrouracil 
• 7697-37-2 nitric acid 
• 480-68-2 dilituric acid 
• 56032-78-1 2,4,6-trioxo-hexahydro-pyrimidine-5-carboxylic acid amide 
• 19645-78-4 5-bromobarbituric acid 
• 67-52-7 BARBITURIC ACID 
• 67-56-1 methanol 

Downstream Products

• 19645-78-4 5-bromobarbituric acid 
• 75-25-2 Bromoform 
• 57-13-6 urea 
• 108-19-0 BIURET 
• 174605-23-3 5-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-2-bromopentyl-aldehyde 
• 24764-97-4 2-bromobutanal 
• 5978-87-0 Lyxoflavin 
• 83-88-5 riboflavin 
• 76-24-4 Alloxantin 
• 88982-70-1 tribromoacetyl-urea 
• 67-52-7 BARBITURIC ACID 
• 506-68-3 bromocyane 
• 444-15-5 5-hydroxybarbituric acid 

Relevant articles and documents

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.

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.

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.