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Basic information

  • Name:

  • Barbituric acid

  • CAS No.:

  • 67-52-7

  • Formula:
  • C4H4N2O3
  • Synonyms:
  • Hexahydropyrimidine-2,4,6-trione;2,4,6-Pyrimidinetrione;Barbitursaeure;Hydrouracil, 6-hydroxy-;2，4，6-Trihydroxypyrimidine(Barbituric acid);2, 4, 6-Trihydroxypyrimidine;Malonylurea;6-Hydroxyuracil;Urea, N,N-(1,3-dioxo-1,3-propanediyl)-;2,4,6-Pyrimidinetriol;pyrimidine-2,4,6(1H,3H,5H)-trione;2,4,6 (1H,3H,5H)-Pyrimidinetrione;Barbituric acid (VAN) (8CI);1,3-diazinane-2,4,6-trione;Pyrimidinetrione;sodium 4,6-dioxo-1H-pyrimidin-2-olate;Urea, N, N-(1,3-dioxo-1,3-propanediyl)-;2,4,6-Trioxohexahydropyrimidine;2,4,6-(1H,3H,5H)-Pyrimidinetrione;Malonylharnstoff;Pyrimidinetriol;1,2,3,4,5,6-Hexahydro-2,4,6-pyrimidinetrione;Barbiturate;2,4,6-Trihydroxypyrimidine;

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Chemistry

IUPAC Name: 1,3-diazinane-2,4,6-trione 
Empirical Formula: C4H4N2O3
Molecular Weight: 128.0862g/mol
EINECS: 200-658-0 
Structure of Barbituric acid (CAS NO.67-52-7):

Melting Point: 248-252 °C (dec.)(lit.)
Boiling Point: 260 °C 
Flash Point: 150 °C
Water Solubility: 142 g/L (20 ºC)
Index of Refraction: 1.492
Molar Refractivity: 25.53 cm3
Molar Volume: 88 cm3
Polarizability: 10.12×10-24cm3
Surface Tension: 48.7 dyne/cm
Density: 1.455 g/cm3 
Product Categories: Pharmaceutical Intermediates;PYRIMIDINE;Miscellaneous Biochemicals;Pyrimidine series 
Canonical SMILES: C1C(=O)NC(=O)NC1=O
InChI: InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
InChIKey: HNYOPLTXPVRDBG-UHFFFAOYSA-N

History

 Barbituric acid (CAS NO.67-52-7) was discovered by the German chemist Adolf von Baeyer on 4. December 1864—the feast of St Barbara and therefore the name given to the compound—by combining urea and malonic acid in a condensation reaction. and The first to be used in medicine was barbital (Veronal) starting in 1903, and the second, phenobarbitone a.k.a. phenobarbital was first marketed in 1912.

Uses

  Barbituric acid (CAS NO.67-52-7) is used in synthesis of riboflavin.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 505mg/kg (505mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 106, Pg. 504, 1986.
rat LD50 oral > 5gm/kg (5000mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.


 

Safety Profile

Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 1
RTECS: CP8000000
HS Code: 29335200

Specification

  Barbituric acid , its cas register number is 67-52-7. It also can be called 2,4,6(1H,3H,5H)-Pyrimidinetrione ; 2,4,6-Pyrimidinetriol ; 2,4,6-Pyrimidinetrione ; 2,4,6-Trihydroxypyrimidine ; 2,4,6-Trioxohexahydropyrimidine ; 6-Hydroxyuracil ;
 Hydrouracil, 6-hydroxy- ; Malonylurea  ; Pyrimidinetriol ; Pyrimidinetrione ; Urea, N,N'-(1,3-dioxo-1,3-propanediyl)- . Barbituric acid (CAS NO.67-52-7) is a cream coloured fine crystalline powder.

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