17013-41-1

Basic information

• Product Name: 5,5-dibutylbarbituric acid
• Synonyms: 5,5-dibutylbarbituric acid;5,5-Dibutylpyrimidine-2,4,6(1H,3H,5H)-trione
• CAS NO: 17013-41-1
• Molecular Formula: C₁₂H₂₀N₂O₃
• Molecular Weight: 240.2988
• EINECS: 241-088-2
• Mol File: 17013-41-1.mol

Chemical Properties

• Boiling Point: 383.02°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.1080 (rough estimate)
• Refractive Index: 1.4760 (estimate)
• CAS DataBase Reference: 5,5-dibutylbarbituric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dibutylbarbituric acid(17013-41-1)
• EPA Substance Registry System: 5,5-dibutylbarbituric acid(17013-41-1)

Safety Data

• Hazardous Substances Data: 17013-41-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H20N2O3/c1-3-5-7-12(8-6-4-2)9(15)13-11(17)14-10(12)16/h3-8H2,1-2H3,(H2,13,14,15,16,17)

Upstream product

• 596-75-8 diethyl dibutylmalonate 
• 57-13-6 urea 
• 133-08-4 diethyl butylmalonate 

Relevant articles and documents

Quantification of cooperativity in the self-assembly of H-bonded rosettes

The self-assembly of triaminopyrimidines with barbiturates and with cyanates was investigated in chloroform solution. Equimolar mixtures of two complementary components form stable macrocyclic 3:3 complexes (rosettes). The thermodynamics of self-assembly were quantified by using 1H NMR titrations to measure the strength of pairwise H-bonding interactions between two rosette components (K), allosteric cooperativity associated with formation of a second H-bonding interaction with each component, and the effective molarity for cyclisation of the rosette motif (EM). Pyrimidine-cyanurate interactions are an order of magnitude more favourable than pyrimidine-barbiturate interactions, so the cyanurate rosettes are significantly more stable than barbiturate rosettes. There is no allosteric cooperativity associated with rosette formation, but the chelate cooperativity quantified by the product K EM is exceptionally high (102-104), indicating that there are no other species present that compete with rosette assembly. The values of EM for rosette formation are approximately 2 M for all four rosettes studied and are not affected by differences in peripheral substituents or intrinsic H-bond strength.

Substituent effects on partition coefficients of barbituric acids

Precise partition coefficients in 1-octanol-water at 25°C were determined for three 2-thiobarbituric acids and 14 barbituric acids with a wider range of substituents. The experimental log P values (log P(exp)) of barbituric acids were correlated with the carbon number and the branching effect of the C5 substituent(s) by linear regression analysis. The carbon number term makes a major contribution to the partition coefficients. The contribution of the polar effect of the C5 substituents was insignificant in contrast to a previous report. Hydrophobic constants (π) were determined for allyl, phenyl, and chloro-substituents, and these emperical π values gave much closer predicted calculated log P (log P(calc)) values when applied to the reported log P(exp) values.