67-52-7 Usage
Chemical Description
Barbituric acid is another small organic molecule that is used as a starting material for the synthesis of various drugs.
Description
Barbituric acid, a compound formed by the condensation of malonic acid and urea, serves as a precursor for the synthesis of various barbiturate agents. Despite its lack of anesthetic properties, the substitution of its C2 and C5 atoms with different groups results in a multitude of barbiturate derivatives with sedative, hypnotic, anticonvulsant, and anesthetic effects.
Uses
Used in Pharmaceutical Industry:
Barbituric acid is used as a precursor for the synthesis of barbiturate agents, which are employed for their sedative, hypnotic, anticonvulsant, and anesthetic properties. Examples of such agents include phenobarbital, amobarbital, thiopental, and methohexital.
Used in Vitamin Production:
Barbituric acid is used as an active ingredient in the production of Vitamin B2, contributing to the synthesis of this essential nutrient.
Used in Chemical Synthesis:
Barbituric acid is utilized as a precursor for the preparation of 5-arylidene barbituric acid through a reaction with aromatic aldehyde. This allows for the creation of various chemical compounds with potential applications.
Used in Electrochemistry:
Barbituric acid is employed in the electrochemical oxidation of iodine, utilizing techniques such as cyclic voltammetry and controlled potential coulometry. This application highlights its versatility in different scientific fields.
Used in Manufacturing Industry:
Barbituric acid is widely used in the manufacturing of plastics, textiles, and polymers, showcasing its importance in various industrial applications. Its strong acidic properties and active methylene group make it a valuable component in these processes.
Preparation
Barbituric acid is derived By the reaction of diethyl malonate and urea. First put Urea in a reaction tank containing methanol ,heat , reflux , dissolve, then add the dried diethyl malonate and sodium methoxide, the reaction is refluxed at 66-68°C for 4-5h, after distillation to recover methanol, cooling to 40-50°C, add dilute hydrochloric acid to adjust to pH 1-2.Cool to room temperature, throw to obtain crude, wash with distilled water once, dry to get crude , and then purify with water and activated carbon, dry to obtain products. Industrial barbituric acid is white or pink crystalline powder, strongly acidic, more than 98% content, melting point ≥245°C. Material consumption fixed: diethyl malonate 1098kg/t, urea 476kg/t, hydrochloric acid (reagent grade III) 681kg/t, sodium methanol (28%) 369kg/t, methanol 1025kg/t.
Reactions
Barbituric acid with aromatic aldehydes was used in an experimental study, meant to demonstrate the increased efficiency of Knoevenagel condensation reaction for barbituric acid and various aromatic aldehydes on basic alumina, in the absence of organic solvents under microwave irradiation. It may also be used in electrochemical oxidation of iodine, using cyclic voltammetry and controlled-potential coulometry.
Purification Methods
Recrystallise it twice from H2O, then dry it for 2 days at 100o. [Beilstein 24 III/IV 1873.]
Check Digit Verification of cas no
The CAS Registry Mumber 67-52-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 7 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 67-52:
(4*6)+(3*7)+(2*5)+(1*2)=57
57 % 10 = 7
So 67-52-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H,(H3,5,6,7,8,9)
67-52-7Relevant articles and documents
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Bolton
, p. 166,170 (1963)
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Ultrasound-assisted rapid synthesis of 2-aminopyrimidine and barbituric acid derivatives
Bayramo?lu, Duygu,Kurtay, Gülbin,Güllü, Mustafa
, p. 649 - 658 (2020/02/11)
Novel, inexpensive, and relatively expeditious procedure to achieve the synthesis of different 2-aminopyrimidine and barbituric acid derivatives is presented here, starting from readily available compounds such as guanidine hydrochloride, urea, 1,3-dialkylurea, or thiourea. Under ultrasonic irradiation, base-driven (Na2CO3, NaOH, or NaOC2H5) heterocyclization reactions of the aforementioned substrates with diethyl malonate, diethyl-2-alkyl malonate, pentane-2,4-dione, or ethyl-3-oxobutanoate yielded corresponding products. Significant advantages of this sonochemical synthetic protocol with regard to the conventional thermal methods include easy reaction setup and work-up steps, reasonably mild conditions, shorter reaction times (～30 min) and comparably high product yields. The characterization of the synthesized compounds was based on melting points, FT-IR, GC-MS, 1H-NMR techniques, and the obtained data were also checked from the previously published studies.
Prebiotic Origin of Pre-RNA Building Blocks in a Urea “Warm Little Pond” Scenario
Menor Salván,Bouza, Marcos,Fialho, David M.,Burcar, Bradley T.,Fernández, Facundo M.,Hud, Nicholas V.
, p. 3504 - 3510 (2020/10/02)
Urea appears to be a key intermediate of important prebiotic synthetic pathways. Concentrated pools of urea likely existed on the surface of the early Earth, as urea is synthesized in significant quantities from hydrogen cyanide or cyanamide (widely accepted prebiotic molecules), it has extremely high water solubility, and it can concentrate to form eutectics from aqueous solutions. We propose a model for the origin of a variety of canonical and non-canonical nucleobases, including some known to form supramolecular assemblies that contain Watson-Crick-like base pairs.The dual nucleophilic-electrophilic character of urea makes it an ideal precursor for the formation of nitrogenous heterocycles. We propose a model for the origin of a variety of canonical and noncanonical nucleobases, including some known to form supramolecular assemblies that contain Watson-Crick-like base pairs. These reactions involve urea condensation with other prebiotic molecules (e. g., malonic acid) that could be driven by environmental cycles (e. g., freezing/thawing, drying/wetting). The resulting heterocycle assemblies are compatible with the formation of nucleosides and, possibly, the chemical evolution of molecular precursors to RNA. We show that urea eutectics at moderate temperature represent a robust prebiotic source of nitrogenous heterocycles. The simplicity of these pathways, and their independence from specific or rare geological events, support the idea of urea being of fundamental importance to the prebiotic chemistry that gave rise to life on Earth.
A compound and its preparation and use (by machine translation)
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Paragraph 0091; 0092; 0093; 0095; 0102; 0104; 0111; 0113, (2018/03/25)
The present invention discloses a structure of the formula X compound or its pharmaceutically acceptable salt and its preparation and use: Wherein R1 is at least comprises a five-membered ring or a six-membered ring of chemical structure; R2 is a molecular weight greater than 100 and chemical structure containing electron-withdrawing group. (by machine translation)
