1-Benzyl-5-phenylbarbituric acid

• CAT Number: R065576
• CAS Number: 72846-00-5
• Molecular Formula: C17H14N2O3
• Molecular Weight: 294.31
• Purity: ≥95%
• Synonyms: 1-benzyl-5-phenylpyrimidine-2,4,6(1h,3h,5h)-trione; Benzyl-5-phenylbarbituric acid; 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-phenyl-1-(phenylmethyl)-;1-benzyl-5-phenyl-1,3-diazinane-2,4,6-trione
• Storage: -20°C
• IUPAC Name: 1-benzyl-5-phenyl-1,3-diazinane-2,4,6-trione
• InChI: InChI=1S/C17H14N2O3/c20-15-14(13-9-5-2-6-10-13)16(21)19(17(22)18-15)11-12-7-3-1-4-8-12/h1-10,14H,11H2,(H,18,20,22)
• InChIKey: KCWWCWMGJOWTMY-UHFFFAOYSA-N
• SMILES: C1=CC=C(C=C1)CN2C(=O)C(C(=O)NC2=O)C3=CC=CC=C3

1-Benzyl-5-phenylbarbituric acid (CAS 72846-00-5) is useful as a pharmaceutical intermediate in organic synthesis. It is often used in the initiator system for acid dental formulations. 



 

Reference

1. Dental materials journal.A review of our development of dental adhesives—Effects of radical polymerization initiators and adhesive monomers on adhesion.Ikemura K, Endo T. 

This paper reviews the development of dental adhesives by collating information of related studies from original scientific papers, reviews, and patent literatures. Through our development, novel radical polymerization initiators, adhesive monomers, and microcapsules were synthesized, and their effects on adhesion were investigated. It was found that 5-monosubstituted barbituric acid (5-MSBA)-containing ternary initiators in conjunction with adhesive monomers contributed to effective adhesion with good polymerization reactivity. Several kinds of novel adhesive monomers bearing carboxyl group, phosphonic acid group or sulfur-containing group were synthesized, and investigated their multi-purpose bonding functions. It was suggested that the flexible methylene chain in the structure of adhesive monomers played a pivotal role in their enhanced bonding durability. It was found that the combination of acidic monomers with sulfur-containing monomer markedly improved adhesion to enamel, dentin, porcelain, alumina, zirconia, non-precious metals and precious metals. A new poly(methyl methacrylate) (PMMA)-type adhesive resin comprising microencapsulated polymerization initiators was also found to exhibit both good formulation stability and excellent adhesive property.


2.Dental materials journal. 2006;25(3):566-75.Design of new phosphonic acid monomers for dental adhesives-synthesis of (Meth) acryloxyalkyl 3-phosphonopropionates and evaluation of their adhesion-promoting functions.

Ikemura K, Tay FR, Nishiyama N, Pashley DH, Endo T.

The aims of this study were to synthesize new phosphonic acid monomers, and to examine their bonding performance. Four kinds of newly designed phosphonic acid monomers were synthesized, and seven experimental composite-type adhesive resins comprising the synthesized monomers (3 wt%), with BPO/ DEPT/ BPBA initiator were prepared. Tensile bond strengths of the adhesive resins to enamel and metal were measured with a universal testing machine at a crosshead speed of 1.0 mm/ min. The synthesized adhesive monomers were light yellow viscous liquids with 32.5%-49.3% yields, and identified by 1H NMR, IR and elemental analysis to be (meth)acryloxyalkyl 3-phosphonopropionates [R-P(=O)(OH)2] (5-MPPP, 6-MHPP, 6-AHPP, 10-MDPP). It was found that the newly developed phosphonic acid monomers with BPO/ DEPT/ BPBA initiator attained strong adhesion to both unetched, ground enamel and sandblasted Ni-Cr alloy with good durability. They exhibited significantly higher bond strengths than conventional phosphorous-containing monomers such as MEPP and VBPA (p<0.01). These findings indicate that the experimental phosphonic acid monomer-containing adhesive resins have potential prosthodontic and orthodontic applications, especially as self-etching, non-rinsing orthodontic adhesive resins.