1,3-Dimethylbarbituric acid Chemical Properties

Melting point:

121-123 °C (lit.) 121-123 °C

Boiling point:

228.1±23.0 °C(Predicted)

Density 

1.322±0.06 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

hot water: soluble0.5g/10 mL, clear, colorless to faintly yellow

form 

Crystalline Powder

pka

pK1:4.68(+1) (25°C)

color 

White/cream/pale yellow

Water Solubility 

Soluble in water.

BRN 

139810

CAS DataBase Reference

769-42-6(CAS DataBase Reference)

NIST Chemistry Reference

1,3-Dimethylbarbituric acid(769-42-6)

EPA Substance Registry System

2,4,6(1H,3H,5H)-Pyrimidinetrione, 1,3-dimethyl- (769-42-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-36/39

WGK Germany 

3

TSCA 

Yes

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1,3-Dimethylbarbituric acid Usage And Synthesis

Chemical Properties

Yellow or brownish powder

Uses

1,3-Dimethylbarbituric acid is used as a catalyst in the Knoevenagel condensation of a series of aromatic aldehydes. It is also used in the synthesis of 5-aryl-6-(alkyl- or aryl-amino)-1,3-dimethylfuro [2,3-d]pyrimidine derivatives and enantioselective synthesis of isochromene pyrimidinedione derivatives.

Uses

1,3-Dimethyl Barbituric Acid (Urapidil Impurity 4) is a derivative of Barbituric acid. All of the barbituric acid derivatives which have been reported to have pronounced hypnotic activity are disubstituted in the 5-position.

General Description

1,3-Dimethylbarbituric acid (1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione) is an active methylene compound. It undergoes hollow Pd₆ water-soluble cage, [{(tmen)Pd}₆(timb)₄](NO₃)₁₂ (tmen= N,N,N′,N′-tetramethylethylenediamine, timb=1,3,5-tris(1-imidazolyl)benzene)-catalyzed Knoevenagel condensation reaction with pyrene-1-carboxaldehyde. It undergoes self-sorted Pd₇ molecular boat having an internal nanocavity (catalyst)-assisted Knoevenagel condensation reaction with various aromatic aldehydes. It has been synthesized by reacting 1,3-dimethylurea, malonic acid and acetic anhydride in acetic acid. It is widely used for the synthesis of various synthetic intermediates and heterocyclic compounds.

Purification Methods

Crystallise the acid from water and sublime it in a vacuum. Also purify it by dissolving 10g in 100mL of boiling CCl4/CHCl3 (8:2) (1g charcoal), filtering and cooling to 25o. Dry it in vacuo [Kohn et al. Anal Chem 58 3184 1986]. [Beilstein 24 III/IV 1875.]

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