5-Methylbarbituric acid

Base Information

• Chemical Name: 5-Methylbarbituric acid
• CAS No.: 2417-22-3
• Deprecated CAS: 37780-27-1,94414-44-5,294851-88-0,328289-32-3,697787-37-4,1257872-56-2,1393847-11-4
• Molecular Formula: C5H6N2O3
• Molecular Weight: 142.114
• Hs Code.: 2933540000
• NSC Number: 30724
• UNII: VUR44R5FYX
• DSSTox Substance ID: DTXSID10178880
• Nikkaji Number: J497.987G
• Wikidata: Q27103739
• Metabolomics Workbench ID: 51736
• Mol file: 2417-22-3.mol

Synonyms:2417-22-3;5-Methylbarbituric acid;5-methylpyrimidine-2,4,6(1H,3H,5H)-trione;Barbituric acid, 5-methyl-;5-Methylbarbiturate;5-Methyl-2,4,6(1H,3H,5H)-pyrimidinetrione;6-Hydroxythymine;5-methyl-1,3-diazinane-2,4,6-trione;6-Hydroxy-5-methyluracil;NSC30724;VUR44R5FYX;2,4,6(1H,3H,5H)-pyrimidinetrione, 5-methyl-;MFCD00233524;NSC 30724;NSC-30724;2,4,6(1H,3H,5H)-Pyrimidinetrione,5-methyl-(9CI);5-methyl barbituric acid;2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl- (9CI);UNII-VUR44R5FYX;SCHEMBL367457;CHEBI:28492;DTXSID10178880;5-Methyl-2,4,6-trihydroxypyrimidine;AKOS000351436;GS-5620;5-methylhexahydropyrimidine-2,4,6-trione;SY122333;CS-0117039;FT-0717521;2,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl-;C05281;2,4,6(1H,3H, 5H)-Pyrimidinetrione, 5-methyl-;Q27103739

Chemical Property of 5-Methylbarbituric acid

Chemical Property:

• Melting Point: 320-323 °C
• Refractive Index: 1.471
• PKA: pK1:3.386(＋1) (25°C)
• PSA: 75.27000
• Density: 1.315 g/cm³
• LogP: -0.35390
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 142.03784206
• Heavy Atom Count: 10
• Complexity: 191

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Methylpyrimidine-2,4,6(1H,3H,5H)-trione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)NC(=O)NC1=O

Technology Process of 5-Methylbarbituric acid

There total 9 articles about 5-Methylbarbituric 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: 19.0%

5-bromo-6-hydroxy-5,6-dihydrothymine (1195-73-9) → 5-methylbarbituric acid (2417-22-3,697787-37-4) + thymin (65-71-4,28806-14-6,691841-57-3) + 6-Hydroxydihydrothymine (13514-92-6)

Guidance literature:

With sodium formate; In water; Irradiation;

DOI:10.1246/cl.1983.1441

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → 5-hydroxymethyl uracil (4433-40-3) + 5-methylbarbituric acid (2417-22-3,697787-37-4) + 6-hydroxy-5,6-dihydrothymine (1123-21-3) + cis-5,6-dihydroxy-5,6-dihydrothymine (1124-84-1,1431-06-7,2943-56-8,57908-05-1,57908-06-2,57968-48-6,57968-49-7,57968-50-0,58000-49-0) + 6-Hydroxydihydrothymine (13514-92-6) + 5,6-dihydrothymine (696-04-8)

Guidance literature:

With ammonium ferric sulfate; In water; Product distribution; γ-radiolysis, absence of NH4Fe(SO4)2, in presence of NH4Fe(SO4)2 and t-butyl alcohol;

DOI:10.1246/bcsj.63.3001

Reference yield:

5-bromo-6-hydroxy-5,6-dihydrothymine (1195-73-9) → 5-methylbarbituric acid (2417-22-3,697787-37-4) + thymin (65-71-4,28806-14-6,691841-57-3) + 6-Hydroxydihydrothymine (13514-92-6) + 5,6-dihydrothymine (696-04-8)

Guidance literature:

With sodium formate; In water; Mechanism; Irradiation; reaction in the presence of aromatic amine or inorganic reductant;

upstream raw materials:

5-bromo-6-hydroxy-5,6-dihydrothymine

cis-5,6-dihydroxy-5,6-dihydrothymine

thymin

5,6-dihydrothymine

Downstream raw materials:

5-ethyl-5-methyl-1H,3H,5H-pyrimidin-2,4,6-trione

6-Methyluracil

5-methyl-5-<(2-methylbenzoylamino)(4-pyridyl)methyl>barbituric acid

5-methyl-5-<(4-nitrobenzoylamino)(4-pyridyl)methyl>barbituric acid

Refernces

• 1、 Bhattacharyya,Mandal,Chakrabarti. "Effect of Fe(III) ions on the γ-radiolysis of thymine". . p. 3001 - 3005. Retrieved 2007/10/02.
• 2、 Nishimoto, Sei-ichi,Ide, Hiroshi,Otsuki, Nobuaki,Nakamichi, Kikumi,Kagiya, Tsutomu. "Radiation-induced Reduction of Thymine Derivatives in Aqueous Solution. Part 4. Promoted Transformation of Thymine Glycol into Thymine by Aromatic Amines and Low-valent Transition Metal Salts". . p. 1127 - 1134. Retrieved 2007/10/02.