2417-22-3

Basic information

• Product Name: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl- (9CI)
• Synonyms: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl- (9CI);5-methyl-1,3-diazinane-2,4,6-trione;5-methylbarbituric acid;5-methylpyrimidine-2,4,6-trione;5-Methyl-2,4,6(1H,3H,5H)-pyrimidinetrione
• CAS NO: 2417-22-3
• Molecular Formula: C₅H₆N₂O₃
• Molecular Weight: 142.11274
• Product Categories: PYRIMIDINE
• Mol File: 2417-22-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 320-323 °C
• Appearance: /
• Density: 1.315 g/cm³
• Refractive Index: 1.471
• PKA: pK1:3.386(＋1) (25°C)
• CAS DataBase Reference: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl- (9CI)(2417-22-3)
• EPA Substance Registry System: 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl- (9CI)(2417-22-3)

Safety Data

• Hazardous Substances Data: 2417-22-3(Hazardous Substances Data)

Usage

General Description

5-methyl-2,4,6(1H,3H,5H)-Pyrimidinetrione, also known as 5-methyl barbituric acid, is a chemical compound with the molecular formula C5H4N2O3. It is a derivative of barbituric acid and is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-methyl- (9CI) has a variety of applications, including as a precursor to the sedative and hypnotic drug phenobarbital, as well as in the production of insecticides and herbicides. It is a white, crystalline solid that is sparingly soluble in water and has a melting point of around 250°C. Due to its potential health and environmental hazards, proper handling and disposal procedures should be followed when working with this compound.

InChI:InChI=1/C5H6N2O3/c1-2-3(8)6-5(10)7-4(2)9/h2H,1H3,(H2,6,7,8,9,10)

Upstream product

• 696-04-8 5,6-dihydrothymine 
• 65-71-4 thymin 
• 1124-84-1 cis-5,6-dihydroxy-5,6-dihydrothymine 
• 1195-73-9 5-bromo-6-hydroxy-5,6-dihydrothymine 

Downstream Products

• 112054-93-0 5-methyl-5-<(2-methylbenzoylamino)(4-pyridyl)methyl>barbituric acid 
• 112054-94-1 5-methyl-5-<(4-nitrobenzoylamino)(4-pyridyl)methyl>barbituric acid 
• 112054-92-9 5-methyl-5-<(3,5-dimethylbenzoylamino)(4-pyridyl)methyl>barbituric acid 
• 67-52-7 BARBITURIC ACID 
• 1113-63-9 2-methyl-malonamide 
• 1780-36-5 5-methyl-2,4,6-trichloropyrimidine 
• 1627-28-7 6-chloro-5-methylpyrimidine-2,4(1H,3H)-dione 
• 136160-18-4 5-methyl-6-(phenylthio)pyrimidine-2,4(1H,3H)-dione 
• 31458-38-5 6-iodo-5-methylpyrimidine-2,4(1H,3H)-dione 
• 132774-39-1 1-(ethoxymethyl)-6-(phenylthio)thymine 
• 123027-56-5 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine 
• 1393847-40-9 1-ethoxymethyl-3,4-dihydro-5-methyl-6-(phenylthio)-4-thioxopyrimidin-2(1H)-one 
• 1393847-36-3 1-(2,5-dimethylbenzyl)-6-(phenylthio)thymine 
• 1393847-35-2 1-ethoxymethyl-6-(3-chlorophenylthio)thymine 

Relevant articles and documents

Reactions of Ni(II) and its complexes with free radicals derived from thymine

The effects of nickel(II) ions and its complexes on the products arising from the γ-radiolysis of thymine were studied.The decomposition of the pyrimidine base and formation of different radiolytic products indicate that nickel(II) ions or its complexes have little effect on the radiosensitivity of thymine.The transient hydroxyl adduct of thymine reacts with Ni(II) with the formation of a complex having a nickel-carbon bond.The rate constants for the reactions are of the order of 106 dm3mol-1s-1.Possible mechanisms for the formation of different products in the radiolysis of thymine in the presence of nickel(II) compounds are discussed.

Far ultraviolet induced decomposition of thymine in deaerated and aerated aqueous solutions

Thymine in aqueous solution was decomposed with quantum yields of 0.3 and 0.4 under N2-saturated and aerated conditions by far-ultraviolet light (>180 nm, far-uv), and quantum yields of 2E-4 and 3E-4 by near-ultraviolet light (>220 nm, near-uv), respectively.The main photolytic products by far-uv were 5,6-dihydrothymine (DHT) (selectivity: S(DHT) = 0.2) and 5-hydroxymethyluracil (HMU) (S(HMU) = 0.1) under N2-saturated conditions. cis- and trans-5,6-Dihydroxy-5,6-dihydrothymine (TG), 6(5)-hydroperoxy-5(6)-hydroxy-5,6-dihydrothymine (HTP) (S(TG) + S(HTP) = 0.2), and N1-formyl-N2-pyruvylurea (FPU) (S(FPU) = 0.4) were obtained under aerated conditions.These products were attributed to the reactions of thymine with the radical H and radical O produced by photolysis of water.

RADIOLYSIS OF DIHYDROURACIL AND DIHYDROTHYMINE IN AQUEOUS SOLUTIONS CONTAINING OXYGEN; FIRST- AND SECOND-ORDER REACTIONS OF THE ORGANIC PEROXYL RADICALS; THE ROLE OF ISOPYRIMIDINES AS INTERMEDIATES

The nature and yields of the products of radiolysis of aqueous solutions of dihydrouracil containing both N2O and O2 strongly depend on pH and dose rate.At a dose rate of 0.3 Gy s-1 and at pH 3, the major products are barbituric acid (G 2.4), labile material (G 2.8), and uracil (G 0.1).The labile material is converted into uracil upon treatment with acid and is largely composed of 5,6-dihydro-6-hydroxyuracil.At pH 7 barbituric acid is absent and uracil becomes the major product (G 4.5); some labile material is also formed (G 0.7).At pH 5 the pattern of the product distribution changes as a function of dose rate.With increasing dose r ate G(uracil) decreases whereas G(barbituric acid) increases.The predominant radical formed in the dihydrouracil system is the 6-peroxyl radical, and it has been found, using pulse radiolysis with both optical and conductometric detection, that this peroxyl radical can eliminate O2-. to give uracil via an unstable isomeric form of the pyrimidine (isouracil).The elimination is base-catalysed so that, under alkaline conditions, uracil is the major radiolysis product.At lower pH, and also at higher dose rates, bimolecular decay of the peroxyl radical competes with the O2-. elimination process, barbituric acid being a specific product of the bimolecular decay route.The mechanism of these processes are discussed.Irradiation of dihydrothymine-N2O-O2 solutions gave similar results.