Grundinformationen
- 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)-trionePyrimidinetriol2,4,6-TrioxohexahydropyrimidineBarbiturateDTXSID8020129CHEBI:16294WQ92Y2793G
Weitere Namen anzeigen
barbituricPyriMidine-2,4,6-triolFluorouracil EP Impurity AHexahydropyrimidine-2,4,6-trioneBARBITURIC ACID, FOR THE DETERMINATION O F CYANIDEBarbitursureARBIBTONE ACID
NSC-7889DTXCID201294,6-dihydroxy-2,5-dihydropyrimidin-2-oneCHEBI:29745RefChem:116475CHEBI:22693200-658-06-Hydroxyuracil
Datenbank-Bezeichner
- CAS
67-52-7- PubChem CID
- 6211
- DTXSID
DTXSID8020129- ChEMBL
CHEMBL574699- ChEBI
CHEBI:16294- UNII
- WQ92Y2793G
- EC Number
- 200-658-0
- Nikkaji
- J348D
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
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
- Schmelzpunkt
- 248 · 248-252 °C (dec.) (lit.)
- Siedepunkt
- 260 ℃ · 260℃ (decomposition)
- Dichte
- 1.6006 · 1.6006 (rough estimate)
- Brechungsindex
- 1.461 · 1.4610 (estimate)
- Flammpunkt
- 150 °C · 150 °C
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 11.45 g/l · 11.45g/l
- Aggregatzustand
- Powder/Solid
- pka
- 4.01 · 4.01(at 25℃)
- Farbe
- Light Cream
- Geruch (Odor)
- Odorless
- PH
- 2 · 2-3 (50g/l, H2O, 60℃)
- Wasserlöslichkeit
- 142 g/L · 142 g/L (20 ºC)
- Merck
- 14 · 14,963
- BRN
- 120502 · 120502
- Kosmetik-Inhaltsstoffe Funktionen
- 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 Datenbank
- 67 · 67-52-7(CAS DataBase Reference)
- NIST chemische Informationen
- Barbituric acid(67-52-7)
- EPA chemische Informationen
- Barbituric acid (67-52-7)
Sicherheit und Regulatorisches
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)
Status: Active Update: 25-11-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/13234
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
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Sicherheitsdaten
- wgk
- 1
- tsca
- TSCA listed
- hs_code
- 29335200
- RTECS-Nr.
- CP8000000
- risk_code
- 36/37/38
- Toxizität
- LD50 orally in Rabbit: > 5000 mg/kg
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
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.
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Ergänzende Hinweise
DefinitionChEBI: 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 an allergen and a xenobiotic. It is a conjugate acid of a barbiturate, a barbiturate(2-) and a barbiturate(1-).
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