PRODUCTS

BARBITURIC ACID

Barbituric acid serves as a versatile precursor for producing a wide range of substituted heterocyclic compounds.
Barbituric acid's molecular structure makes it useful in condensation reactions and the development of specialty chemical intermediates.
Barbituric acid is commonly employed in laboratory research, medicinal chemistry, and advanced organic synthesis.

CAS Number 67-52-7
EC Number: 200-658-0
Molecular Formula: C4H4N2O3
Molecular Weight: 128.09

Synonyms: BARBITURIC ACID, 67-52-7, Malonylurea, Pyrimidinetrione, 2,4,6(1H,3H,5H)-Pyrimidinetrione, pyrimidine-2,4,6(1H,3H,5H)-trione, Pyrimidinetriol, 2,4,6-Trioxohexahydropyrimidine, Barbiturate, DTXSID8020129, CHEBI:16294, WQ92Y2793G, NSC-7889, DTXCID20129, 4,6-dihydroxy-2,5-dihydropyrimidin-2-one, CHEBI:29745, RefChem:116475, CHEBI:22693, 200-658-0, 6-Hydroxyuracil, 1,3-diazinane-2,4,6-trione, 2,4,6-Trihydroxypyrimidine, 2,4,6-Pyrimidinetrione, Hexahydropyrimidine-2,4,6-trione, Malonylharnstoff, Barbitursaeure, Barbituric acid (VAN), Hydrouracil, 6-hydroxy-, Fluorouracil EP Impurity A, 2,4,6-Pyrimidinetrione(1H,3H,5H), Urea, N,N'-(1,3-dioxo-1,3-propanediyl)-, MFCD00006666, 1,2,3,4,5,6-Hexahydro-2,4,6-pyrimidinetrione, NSC 7889, 1,3,5-trihydropyrimidine-2,4,6-trione, EINECS 200-658-0, barbituric, Barbitursaure, UNII-WQ92Y2793G, AI3-02724, pyrimidine-2, Barbituric acid (VAN) (8CI), BR8, 2,6-Pyrimidinetriol, 2,4,6-(1H,3H,5H)-Pyrimidinetrione, bmse000346, Epitope ID:120355, EC 200-658-0, Fluorouracil impurity A CRS, SCHEMBL38707, SCHEMBL45717, BARBITURIC ACID [MI], 2,6-Trioxohexahydropyrimidine, SCHEMBL438738, SCHEMBL438739, SCHEMBL962989, 2-hydroxypyrimidine-4,6-dione, orb3029109, orb3141433, SCHEMBL9941322, NSC7889, 2,6(1H,3H,5H)-Pyrimidinetrione, Tox21_200924, BBL036209, SBB004242, STK317809, 2,6-(1H,3H,5H)-Pyrimidinetrione, AKOS000288853, AKOS024255606, 2,4,6-(1H,3H,5H)pyrimidinetrione, BS-3763, CS-W018516, Barbituric acid, ReagentPlus(R), 99%, CAS-67-52-7, NCGC00248877-01, NCGC00258478-01, NN'-(1,3-dioxo-1,3-propanediyl)-Urea, Urea,N'-(1,3-dioxo-1,3-propanediyl)-, N,N'-(1,3-Dioxo-1,3-propanediyl)-Urea, B0003, FLUOROURACIL IMPURITY A [EP IMPURITY], NS00009292, ST45058789, EN300-19230, C00813, Barbituric Acid(Discontinued,See C4X-164915), Q410278, T205940, 2,4,6(1H,3H,5H)-Pyrimidinetrione (ACD/Name 4.0), F0001-1773, Z104473234, 4A0BDFFD-9542-4996-A89F-E5A55D03B250, Barbituric acid, for spectrophotometric det. of cyanide, >=99.5%, Fluorouracil impurity A, European Pharmacopoeia (EP) Reference Standard, InChI=1/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9

Barbituric acid is an organic compound based on a pyrimidine heterocyclic skeleton.
Barbituric acid is an odorless powder soluble in water.

Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active.
Barbituric acid was first synthesised by Adolf von Baeyer.

Barbiturate is a class of drugs characterized as central nervous system (CNS) depressants.
Barbiturate compounds bind to the gamma amino butyric acid (GABA)-A receptor, thereby increasing the influx of chloride ions into the neuron and subsequently causing hyperpolarization, which produces a decrease in neuronal transmission.

Other barbiturate effects in the CNS may include modulation of sodium and calcium channels as well as inhibition of glutamate-mediated excitation.
Although the effects of barbiturates are seen throughout the CNS, the predominant effect occurs in the midbrain region, the part of the brain associated with arousal.
CNS depressive effects associated with this drug class include mild sedation, hypnosis, anesthesia, and coma as well as a decrease in seizure activity.

Barbituric acid is an organic heterocyclic compound derived from pyrimidine and contains three carbonyl groups within a six-membered ring structure.
Barbituric acid is also known as malonylurea because it can be prepared conceptually from malonic acid and urea.

Barbituric acid itself has little pharmacological activity, but its substituted derivatives form the important class of compounds known as barbiturates.
Barbituric acid is widely used as a chemical intermediate in organic synthesis, pharmaceutical research, heterocyclic chemistry, and the preparation of dyes and analytical reagents.

Barbituric acid is a useful acid for organic and drug syntheses.
Barbituric acid's dihydrate form can be synthesized from barbituric acid via crystallization from aqueous solution.

Crystal structure of barbituric acid (in tautomeric form) has been investigated by a three dimensional fourier transform method.
Barbituric acid's enol crystal form has been reported to be thermodynamically stable.

Barbiturates are derivatives of barbituric acid, barbituric acid is formed by the condensation of malonic acid and urea, itself has no anesthetic effect, but if its C2 and C5 atoms are substituted by different genes, it can generate many species of barbiturate agents ,for example, oxygen of C2 is replaced by sulfur, which generates sulfur barbiturates, such as thiopental.
Barbiturates'mechanism is basically the same, they act on different levels of the central nervous system, and have a non-specific inhibition.

Barbituric acid's sedative and hypnotic effects may be related to selective inhibition of thalamic reticular upstream activating system, thereby blocking the excite transduction to cerebral cortex.
Barbituric acid's Anticonvulsant effect is performed through inhibiting synaptic transmission in the central nervous system ,to improve the electrical stimulation threshold in motor cortex.

Barbiturates having a therapeutic effect play a inhibiting role in the central nervous system, such as phenobarbital (phenobarbitone), amobarbital (amylobarbitone), thiopental, methohexital (methohexi-tone ).
Inhibitory barbiturates have sedative, hypnotic, anticonvulsant and anesthetic effects, but its sedative-hypnotic agent has been eliminated, because in the process it is easy to produce severe tolerance, drug dependence and drug liver enzyme induction.

Because of some differences in their chemical structure, the body eliminate and fat-soluble manner of every drug are different, thus the speed of appearing effect and time of continuing also vary.
Long-acting barbiturates such as phenobarbital (phenobarbi-tone) are still used in the treatment of epilepsy anticonvulsant.

Ultrashort acting barbiturates (thiopental and methohexital) are often applied as an intravenous anesthetic.
Barbiturate intravenous anesthetics used clinically are now about ten kinds, but three to five species are commonly used.

According to the view of Anesthesiology, barbiturates can be divided into two categories, namely hypnotic barbiturates and barbiturate anesthesia.
The former are markedly slower drugs such as phenobarbital, having a sedative effect, before anesthesia, Barbituric acid's administration can make the patient quiet.

After intravenous injection of the latter, consciousness soon disappear, Barbituric acid is mainly used for general anesthesia, in which the most commonly used drug is thiopental, so this drug is representative.
Phenobarbital is a barbituric acid derivative, having weak acid, Barbituric acid is the central inhibitor, mainly inhibiting brain ascending reticular activating system.

The shallow to deep degree of inhibition of the drug are due to the amount of small to large, Barbituric acid has different levels of sedative, hypnotic and anticonvulsant, anesthetic effect.
In addition, the drug also has antiepileptic effect.
The above information is edited by the chemicalbook of Tian Ye.

Barbituric acid is a barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups.
Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active.

Barbituric acid has a role as a xenobiotic and an allergen.
Barbituric acid is a conjugate acid of a barbiturate, a barbiturate(2-) and a barbiturate(1-).

Barbituric acid is defined as a compound formed by the condensation of malonic acid and urea, characterized by its structure as 2,4,6-trioxohexahydropyrimidine.
Barbituric acid lacks central depressant activity but serves as a precursor for barbiturates that can exhibit sedative-hypnotic and anticonvulsant properties.

Barbituric acid is widely used in the manufacturing of plastics, textiles, polymers and pharmaceuticals.
Barbituric acid is an active ingredient in the production of Vitamin B2.

Barbituric acid is a strong acid in an aqueous medium with an active methylene group involved Knoevenegal condensation.
Barbituric acid is used as precursor for the preparation of 5-arylidene barbituric acid by reacting with aromatic aldehyde.
Barbituric acid is also used in electrochemical oxidation of iodine using cyclic voltammetry and controlled potential coulometry.

Barbituric Acid is an important heterocyclic organic compound widely used as a key intermediate in pharmaceutical synthesis and chemical research.
Barbituric acid serves as the core structure for barbiturate derivatives, which are used in sedative, hypnotic, and anticonvulsant drug development.

Although Barbituric Acid itself has limited direct therapeutic use, it is essential in the synthesis of numerous active pharmaceutical ingredients.
Barbituric Acid appears as a white crystalline powder with good thermal stability and predictable reactivity.

Barbituric acid is soluble in hot water and polar solvents, making it suitable for controlled chemical reactions and formulation research.
Barbituric acid's well-defined chemical structure and consistency make it valuable in pharmaceutical manufacturing and laboratory applications.

Naming:
Barbituric acid remains unclear why Baeyer chose to name the compound that he discovered "barbituric acid".
In his textbook Organic Chemistry, the American organic chemist Louis Frederick Fieser (1899–1977) initially speculated that the name stemmed from the German word Schlüsselbart (literally, the beard (Bart, Latin: barba) of a key (Schlüssel), that is, the bit of a key), because Baeyer had regarded barbituric acid as central (or "key") to understanding uric acid and its derivatives.

However, Fieser subsequently decided that Baeyer had named Barbituric acid after a young lady whom he had met and who was called "Barbara"' hence the name "barbituric acid" was a combination of the name "Barbara" and "uric acid".
Other sources claim that Baeyer named Barbituric acid after Saint Barbara, either because he discovered it on the feast day of St. Barbara (December 4) or because he sometimes lunched with artillery officers and St. Barbara is their patron saint.

Uses of Barbituric Acid:
Using the Knoevenagel condensation reaction, barbituric acid can form a large variety of barbiturate drugs that behave as central nervous system depressants.
As of 2007, more than 2550 barbiturates and related compounds have been synthesised, with 50 to 55 in clinical use around the world at present.
The first to be used in medicine was barbital (Veronal) starting in 1903, and the second, phenobarbital was first marketed in 1912.

Barbituric acid is a chemical building block in the laboratory synthesis of riboflavin (vitamin B2) and in a method of producing the pharmaceutical drug minoxidil.
Barbituric acid is one of the four ingredients in the synthesis of riboflavin.
Before barbituric acid was substituted in the synthesis of riboflavin, it was too expensive to synthesize riboflavin.

Barbituric acid is used as an intermediate in the synthesis of barbiturate derivatives and other heterocyclic compounds.
Barbituric acid is employed in pharmaceutical and medicinal chemistry research for developing biologically active molecules.

Barbituric acid is also used in the preparation of dyes, pigments, and color-forming compounds through condensation reactions.
Barbituric acid serves as a building block in organic synthesis because its active methylene group readily participates in various chemical transformations.

Barbituric acid is used in analytical chemistry and laboratory research as a reagent for studying reaction mechanisms and molecular interactions.
Barbituric acid is also applied in the synthesis of functional materials and specialized research chemicals.

Barbituric acid is widely used in the manufacturing of plastics, textiles, polymers and pharmaceuticals.
Barbituric acid is an active ingredient in the production of Vitamin B2.

Barbituric acid may be used in the preparation of the corresponding hemiaminals, via chemoselective reduction in the presence of SmI2/H2O reagent.
Barbituric acid may be used in the preparation of BA- modified conjugated carbon nitride nanosheets.

Barbituric acid may be used to synthesize:
5-ylidenebarbituric acid derivatives via Knoevenagel condensation with aromatic and α,β-conjugated aromatic aldehydes
5-diaminomethylenebarbiturates by reacting with substituted carbodiimides

Industry Uses:
Pigment

Applications of Barbituric Acid:
Barbituric acid is widely used in the manufacturing of plastics, textiles, polymers and pharmaceuticals.
Barbituric acid is an active ingredient in the production of Vitamin B2.

Barbituric acid is a parent compound of barbiturate drugs.
Unsubstituted barbituric acid has no hypnotic properties.

Pharmaceutical Intermediates:
Barbituric acid is used in the synthesis of barbiturate derivatives
Barbituric acid is applied in sedative and anticonvulsant drug development
Barbituric acid is essential building block in pharmaceutical chemistry

Chemical & Pharmaceutical Research:
Barbituric acid is used in heterocyclic compound research
Barbituric acid is applied in reaction mechanism and synthesis studies

Academic & Analytical Applications:
Barbituric acid is used in teaching and analytical chemistry studies
Barbituric acid is applied in reference and comparative chemical analysis
Barbituric acid supports structure–activity relationship research

Specialty Chemical Manufacturing:
Barbituric acid is used in the production of fine chemicals and intermediates
Barbituric acid is applied in custom synthesis and contract manufacturing
Barbituric acid ensures reproducible chemical performance

Properties of Barbituric Acid:
The α-carbon atom has a reactive hydrogen atom and is quite acidic (pKa = 4.01) even for a diketone species (cf. dimedone with pKa 5.23 and acetylacetone with pKa 8.95) because of the additional aromatic stabilization of the carbanion.

Synthesis of Barbituric Acid:
Barbituric acid was first prepared and named in 1864 by the German chemist Adolf von Baeyer, by reducing what Baeyer called Alloxanbromid (alloxan dibromide) with hydrocyanic acid, and later by reducing dibromobarbituric acid with a combination of sodium amalgam and hydrogen iodide.
In 1879, the French chemist Édouard Grimaux synthesized barbituric acid from malonic acid, urea, and phosphorus oxychloride (POCl3).
Malonic acid has since been replaced by diethyl malonate because using the ester avoids the problem of having to deal with the acidity of the carboxylic acid and its unreactive carboxylate.

Reactions of Barbituric Acid:
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.
Barbituric acid may also be used in electrochemical oxidation of iodine, using cyclic voltammetry and controlled-potential coulometry.

Preparation of Barbituric Acid:
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.

Stability and Reactivity of Barbituric Acid:

Chemical stability:
Stable under normal storage and handling conditions.

Conditions to avoid:
Avoid excessive heat, moisture, and incompatible materials.

Incompatible materials:
Strong oxidizing agents, acids, and bases.

Hazardous decomposition products:
May produce carbon oxides and nitrogen-containing fumes upon decomposition.

Handling and Storage of Barbituric Acid:

Safe handling:
Avoid dust formation and contact with skin and eyes.
Use adequate ventilation.

Storage conditions:
Store tightly closed in a cool, dry, well-ventilated place.

First Aid Measures of Barbituric Acid:

Inhalation:
Move to fresh air and seek medical attention if symptoms persist.

Skin contact:
Wash with soap and water.

Eye contact:
Rinse with water for several minutes.

Ingestion:
Rinse mouth and seek medical advice if necessary.

Firefighting Measures of Barbituric Acid:

Suitable extinguishing media:
Use water spray, foam, dry chemical, or CO₂.

Protective equipment:
Firefighters should wear suitable protective equipment.

Accidental Release Measures of Barbituric Acid:

Personal precautions:
Avoid dust formation and ensure ventilation.

Cleanup methods:
Collect carefully into a suitable closed container.

Exposure Controls / Personal Protective Equipment of Barbituric Acid:

Engineering controls:
Provide adequate ventilation.

Personal protection:
Wear protective gloves, safety glasses, and suitable clothing.
Use respiratory protection if dust is generated.

Identifiers of Barbituric Acid:
CAS No: 67-52-7
Chemical Name: Barbituric acid
CBNumber: CB0258599
Molecular Formula: C4H4N2O3
Molecular Weight: 128.09
MDL Number: MFCD00006666
MOL File: 67-52-7.mol

Empirical Formula (Hill Notation): C4H4N2O3
CAS Number: 67-52-7
Molecular Weight: 128.09
UNSPSC Code: 12352100
PubChem Substance ID: 24851157
NACRES: NA.21
EC Number: 200-658-0
MDL number: MFCD00006666
Beilstein/REAXYS Number: 120502
Assay: 99%
Form: powder

Article No.: 01639
Grade: For Synthesis
Purity: 99%
CAS No.: 67-52-7
Molecular Formula: C4H4N2O3
Molecular Weight: 128.09
H.S. Code: 2933.5200

Product Number: B1063
Purity / Analysis Method : >99.0%(T)
Molecular Formula / Molecular Weight: C4H4N2O3 = 128.09
Physical State (20 deg.C): Solid
Storage Temperature : Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 67-52-7
Reaxys Registry Number: 120502
SDBS (AIST Spectral DB): 1686
Merck Index (14): 963
MDL Number: MFCD00006666

CAS Number: 67-52-7
Beilstein Reference: 120502
ChEBI: CHEBI:16294
ChEMBL: ChEMBL574699
ChemSpider: 5976
ECHA InfoCard: 100.000.598
EC Number: 200-658-0
Gmelin Reference: 101571
KEGG: C00813
PubChem CID: 6211
UNII: WQ92Y2793G
CompTox Dashboard (EPA): DTXSID8020129
InChI: InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
Key: HNYOPLTXPVRDBG-UHFFFAOYSA-N
InChI=1/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
Key: HNYOPLTXPVRDBG-UHFFFAOYAE
SMILES: O=C1NC(=O)NC(=O)C1

CAS: 67-52-7
IUPAC Name: 1,3-diazinane-2,4,6-trione
Molecular Formula: C4H4N2O3
InChI Key: HNYOPLTXPVRDBG-UHFFFAOYSA-N
SMILES: O=C1CC(=O)NC(=O)N1
Molecular Weight (g/mol): 128.09

Properties of Barbituric Acid:
Chemical formula: C4H4N2O3
Molar mass: 128.087 g·mol−1
Appearance: White crystals
Melting point: 245 °C (473 °F; 518 K)
Boiling point: 260 °C (500 °F; 533 K)
Solubility in water: 142 g/L (20 °C)
Acidity (pKa): 4.01 (H2O)
Magnetic susceptibility (χ): −78.6·10−6 cm3/mol crystal+2H20, −53.8·10−6 cm3/mol Anhy.

Physical state at 20 °C: Solid
Colour: White powder
Odour: Odorless
Melting point/ Freezing point [°C]: 248 - 252 °C
Flash point [°C]: 150°C
Boiling point [°C]: 260°C
Solubility in water [% weight]: Patially soluble in water

Molecular Weight: 128.09 g/mol
XLogP3: -1.5
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 0
128.02219199 Da
Monoisotopic Mass: 128.02219199 Da
Topological Polar Surface Area: 75.3 Å²
Heavy Atom Count: 9
Complexity: 168
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Product Name: Barbituric acid, ReagentPlus®, 99%
Quality Segment: 200
product line: ReagentPlus®
assay: 99%
form: powder
mp: 248-252 °C ((lit.)), 248-252 °C (dec.) (lit.)
SMILES string: [O=C1CC(=O)NC(=O)N1], O=C1CC(=O)NC(=O)N1
InChI: [1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)], 1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
InChI key: [HNYOPLTXPVRDBG-UHFFFAOYSA-N], HNYOPLTXPVRDBG-UHFFFAOYSA-N

Melting point: 248-252 °C (dec.) (lit.)
Boiling point: 260℃ (decomposition)
Density: 1.6006 (rough estimate)
bulk density: 720kg/m3
refractive index: 1.4610 (estimate)
Flash point: 150 °C
storage temp.: Store below +30°C.
solubility: 11.45g/l
form: Powder/Solid
pka: 4.01(at 25℃)
color: Light Cream
Odor: Odorless
PH: 2-3 (50g/l, H2O, 60℃)
Water Solubility: 142 g/L (20 ºC)
Merck: 14,963
BRN: 120502
Cosmetics Ingredients Functions: SKIN CONDITIONING - EMOLLIENT
InChI: 1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
InChIKey: HNYOPLTXPVRDBG-UHFFFAOYSA-N
SMILES: O=C1CC(=O)NC(=O)N1
CAS DataBase Reference: 67-52-7(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: WQ92Y2793G
NIST Chemistry Reference: Barbituric acid(67-52-7)
EPA Substance Registry System: Barbituric acid (67-52-7)
UNSPSC Code: 41116107
NACRES: NA.24

Specifications of Barbituric Acid:
Appearance (Color): White to cream
Identification (FTIR): Conforms
Assay (Aqueous acid-base Titration): ≥98.5 to ≤101.5%
Form: Powder
Melting Point: ca. 245-255?C dec.

Names of Barbituric Acid:

Preferred IUPAC name:
1,3-Diazinane-2,4,6-trione

Other names:
2,4,6(1H,3H,5H)-Pyrimidinetrione
Pyrimidine-2,4,6(1H,3H,5H)-trione
2,4,6-Trioxohexahydropyrimidine
2,4,6-Trihydroxypyrimidine
2,4,6-Trioxypyrimidine
2,4,6-Pyrimidinetriol
2,4,6-Pyrimidinetrione
Pyrimidinetriol
2,4,6-Trihydroxy-1,3-diazine
N,N-Malonylurea
Malonylurea
6-Hydroxyuracil
6-Hydroxy-hydrouracil
N,N-(1,3-Dioxo-1,3-propanediyl)urea