Barbitursure
Barbituric Acid
Grundinformationen
- CAS
67-52-7- Standard-SMILES
O=C1CC(=O)NC(=O)N1- InChIKey
HNYOPLTXPVRDBG-UHFFFAOYSA-N- Summenformel
- C4H4N2O3
- Durchschnittliche Molmasse
- 128,09 g/mol
- Monoisotopische Masse
- 128,02219199
Überblick
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. It has a role as a xenobiotic and an allergen. It is a conjugate acid of a barbiturate, a barbiturate(2-) and a barbiturate(1-).
Namen und Bezeichner
- Bevorzugter Name
- Barbituric Acid
- IUPAC
- 1,3-diazinane-2,4,6-trione
- Lokaler Name
- Barbitursure
- Englischer Name
- Barbituric acid
- Summenformel
- C4H4N2O3
- Molmasse
- 128.09
Namen und Synonyme
BARBITURIC ACID67-52-7MalonylureaPyrimidinetrione2,4,6(1H,3H,5H)-Pyrimidinetrionepyrimidine-2,4,6(1H,3H,5H)-trioneBarbiturate2,4,6-TrioxohexahydropyrimidineDTXSID8020129CHEBI:16294WQ92Y2793GNSC-7889
Weitere Namen anzeigen
barbituricPyriMidine-2,4,6-triolFluorouracil EP Impurity AHexahydropyrimidine-2,4,6-trioneBARBITURIC ACID, FOR THE DETERMINATION O F CYANIDEBarbitursureARBIBTONE ACID
DTXCID201294,6-dihydroxy-2,5-dihydropyrimidin-2-oneCHEBI:29745RefChem:116475CHEBI:22693200-658-0Pyrimidinetriol6-Hydroxyuracil
Datenbank-Bezeichner
- CAS
67-52-7- PubChem CID
- 6211
- DTXSID
DTXSID8020129
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,5
- Polarare Oberfläche (TPSA)
- 75,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 168
Experimentelle und physikochemische Eigenschaften
Chemical ClassesNitrogen Compounds -> Pyrimidines
DrugsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
SpringerMaterials PropertiesBoiling point
LogP
-1.47
-1.41
Solubility1.9e-05 mg/mL at 37 °C
Melting Point248 °C
Physical Description
Dry Powder
White powder; [Alfa Aesar MSDS]
Solid
Collision Cross Section112.69 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physikochemische Eigenschaften
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 35.7% (60 of 168) of reports.
Warning
H315 (63.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 168 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: 2,4,6(1H,3H,5H)-Pyrimidinetrione
2,4,6(1H,3H,5H)-Pyrimidinetrione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,4,6(1H,3H,5H)-Pyrimidinetrione are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: Barbituric acid (EC: 200-658-0)
2,4,6(1H,3H,5H)-Pyrimidinetrione: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Unsubstituted barbituric acid has no hypnotic properties. [Merck Index] Causes somnolence, impaired liver function tests, depressed renal function tests, and other changes in urine composition in acute inhalation studies of rats; Causes somnolence and ataxia in oral lethal-dose studies of mice and rats; Causes somnolence and impaired liver function tests in 30-day intermittent inhalation studies of rats; [RTECS] An irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (63.1%)
Toxikologische Informationen
Chemie und Industrie
Verwendung und Herstellung
UsesUsed to make plastics and pharmaceuticals; [Merck Index]
U.S. Production2023: 30,291 lb
Industry UsesPigment
General Manufacturing Information
Synthetic Dye and Pigment Manufacturing
2,4,6(1H,3H,5H)-Pyrimidinetrione: ACTIVE
Darstellung
synthetischeBarbituric 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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Zugehörige Reaktionen
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