Phenylmethylbarbituric acid

Base Information

• Chemical Name: Phenylmethylbarbituric acid
• CAS No.: 76-94-8
• Molecular Formula: C11H10 N2 O3
• Molecular Weight: 218.212
• European Community (EC) Number: 200-994-8
• NSC Number: 80543
• UNII: GFR227X6YY
• DSSTox Substance ID: DTXSID00226900
• Nikkaji Number: J4.554C
• Wikipedia: Heptobarbital
• Wikidata: Q15409436
• ChEMBL ID: CHEMBL329617
• Mol file: 76-94-8.mol

Synonyms:Phenylmethylbarbituric acid;Heptobarbital;Mephebarbital;Eudan;Rutonal;Methylphenylbarbital;76-94-8;5-Methyl-5-phenylbarbituric acid;5-Methyl-5-phenylbarbityric acid;5-methyl-5-phenyl-1,3-diazinane-2,4,6-trione;Barbituric acid, 5-methyl-5-phenyl-;5-Phenyl-5-methylbarbituric acid;NSC 80543;2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl-5-phenyl-;5-Methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione;EINECS 200-994-8;UNII-GFR227X6YY;BRN 0201825;GFR227X6YY;CHEMBL329617;C11H10N2O3;NSC-80543;5-methyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trione;5-Methyl-5-phenyl-pyrimidine-2,4,6-trione;5-24-09-00283 (Beilstein Handbook Reference);5-methyl-5-phenyl-barbituric acid;D09GIL;SCHEMBL77738;5-methyl-5-phenylbarbitursyre;DTXSID00226900;CHEBI:134900;NSC80543;BDBM50099127;STK299179;PHENYLMETHYLBARBITURIC ACID [MI];LS-24631;PHENOBARBITAL IMPURITY C [EP IMPURITY];PHENOBARBITAL SODIUM IMPURITY C [EP IMPURITY];Q15409436;2,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl-5-phenyl-;Phenylmethylbarbituric Acid (5-Methyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trione)

Chemical Property of Phenylmethylbarbituric acid

Chemical Property:

• Melting Point: 226°
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 358.89°C (rough estimate)
• PKA: pK1:8.011(0) (25°C)
• PSA: 75.27000
• Density: 1.278g/cm³
• LogP: 0.96790
• Water Solubility.: 0.91g/L(25 oC)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 218.06914219
• Heavy Atom Count: 16
• Complexity: 325

Purity/Quality:

99% ^*data from raw suppliers

5-METHYL-5-PHENYLBARBITURIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=O)NC(=O)NC1=O)C2=CC=CC=C2
• Uses: Phenobarbital (P316760) impurity.

Technology Process of Phenylmethylbarbituric acid

There total 8 articles about Phenylmethylbarbituric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

urea (57-13-6) + diethyl 2-methyl-2-phenylmalonate (34009-61-5) → 5-methyl-5-phenylbarbituric acid (76-94-8)

Guidance literature:

With sodium ethanolate;

Reference yield:

dimethyl 2-phenylmalonate (37434-59-6) → 5-methyl-5-phenylbarbituric acid (76-94-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran

1.2: tetrahydrofuran

2.1: Mg(OCH₃)2 / methanol / Heating

With sodium hydride; magnesium methanolate; In tetrahydrofuran; methanol;

DOI:10.1016/S0960-894X(01)00104-4

Reference yield:

benzeneacetic acid methyl ester (101-41-7) → 5-methyl-5-phenylbarbituric acid (76-94-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / Heating

2.1: NaH / tetrahydrofuran

2.2: tetrahydrofuran

3.1: Mg(OCH₃)2 / methanol / Heating

With sodium hydride; magnesium methanolate; In tetrahydrofuran; methanol;

DOI:10.1016/S0960-894X(01)00104-4

upstream raw materials:

urea

diethyl 2-methyl-2-phenylmalonate

2-methyl-2-phenylmalonic acid dimethyl ester

dimethyl 2-phenylmalonate

Downstream raw materials:

5-methyl-5-phenyl-1,3-di-xanthen-9-yl-pyrimidine-2,4,6-trione

1,3-bis(propionyloxymethyl)-5-methyl-5-phenylbarbital

(R)-5-methyl-5-phenyl-1-(propionyloxymethyl)barbital

5-methyl-5-(3-nitro-phenyl)-barbituric acid

Refernces

• 1、 Foley, Louise H,Palermo, Robert,Dunten, Pete,Wang, Ping. "Novel 5,5-disubstitutedpyrimidine-2,4,6-triones as selective MMP inhibitors". . p. 969 - 972. Retrieved 2007/10/03.