5417-13-0

Basic information

• Product Name: 2,4,5,6(1H,3H)-Pyrimidinetetrone,1,3-dimethyl-, 5-oxime
• Synonyms: 5-hydroxyimino-1,3-dimethyl-1,3-diazinane-2,4,6-trione; Alloxan,1,3-dimethyl-, 5-oxime; Alloxan, dimethyl-, 5-oxime; 1,3-Dimethylvioluric acid; Dimethylvioluric acid; NSC 14273; NSC 7370
• CAS NO: 5417-13-0
• Molecular Formula: C₆H₇N₃O₄
• Molecular Weight: 185.1375
• Mol File: 5417-13-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 312.4°Cat760mmHg
• Flash Point: 142.7°C
• Density: 1.61g/cm³
• CAS DataBase Reference: 2,4,5,6(1H,3H)-Pyrimidinetetrone,1,3-dimethyl-, 5-oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5,6(1H,3H)-Pyrimidinetetrone,1,3-dimethyl-, 5-oxime(5417-13-0)
• EPA Substance Registry System: 2,4,5,6(1H,3H)-Pyrimidinetetrone,1,3-dimethyl-, 5-oxime(5417-13-0)

Safety Data

• Hazardous Substances Data: 5417-13-0(Hazardous Substances Data)

Usage

Description

2,4,5,6(1H,3H)-Pyrimidinetetrone,1,3-dimethyl-, 5-oxime, also known as dimethyloximino-4,5,6(1H,3H)-pyrimidinetrione, is an organic compound with the molecular formula C6H6N4O3. It is a pyrimidine derivative characterized by its white solid appearance and sparing solubility in water. The presence of the oxime group in its structure makes it a potential candidate for a range of bioactive compounds and research in various fields. It is stable under normal conditions and is used as an intermediate in the preparation of various other organic compounds, including pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
2,4,5,6(1H,3H)-Pyrimidinetetrone,1,3-dimethyl-, 5-oxime is used as a key intermediate in the synthesis of certain pharmaceuticals. Its unique structure and properties make it a valuable component in the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical industry, 2,4,5,6(1H,3H)-Pyrimidinetetrone,1,3-dimethyl-, 5-oxime is utilized in the synthesis of various agrochemicals. Its role as an intermediate allows for the creation of compounds that can be used in pest control, crop protection, and other agricultural applications.
Used in Organic Chemistry Research:
2,4,5,6(1H,3H)-Pyrimidinetetrone,1,3-dimethyl-, 5-oxime is also used as a research compound in organic chemistry. Its unique structure and properties make it an interesting subject for study, potentially leading to new discoveries and applications in the field of chemistry.

Upstream product

• 2757-85-9 1,3-dimethylalloxan 
• 6632-68-4 6-amino-1,3-dimethyl-5-nitroso-1H-pyrimidine-2,4-dione 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 769-42-6 1,3-dimethylbarbituric acid 
• 598-94-7 1,1-Dimethylurea 
• 105-53-3 diethyl malonate 
• 58378-09-9 1,3,1',3'-tetramethylhydurilic acid 
• 21544-73-0 5,5-dichloro-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 

Downstream Products

• 21620-13-3 7-Amino-1,3-dimethyl-alloxazin 
• 67934-78-5 5-hydroxy-1,3-dimethyl-barbituric acid 
• 21544-73-0 5,5-dichloro-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 
• 14305-99-8 1,3-dimethyl-5-nitro-pyrimidin-2,4,6(1H,3H,5H)-trione 
• 2757-85-9 1,3-dimethylalloxan 
• 7803-49-8 hydroxylamine 
• 769-42-6 1,3-dimethylbarbituric acid 

Relevant articles and documents

Complexes with 6-amino-5-nitroso-2-thiouracil and violuric acid derivatives containing the fac-ReI(CO)3 core: Synthesis, XRD structural and photoluminescence characterization

The fac-tricarbonylrhenium(I) complexes of the 6-amino-1,3-dimethyl-5- nitroso-2-thiouracil (DANTU) and violuric acid (VIO) and its mono- (MVIO) and dimethyl (DVIO) derivatives have been prepared. The complexes have been characterized by elemental analysis, IR, 1H and 13C NMR spectral methods and luminescence spectroscopy. The structures of [ReCl(CO) 3(DANTU)], [Re(H2O)(CO)3(VIOH-1)] and [Re(H2O)(CO)3(DVIOH-1)] complexes were solved from single-crystal X-ray diffraction experiments. The coordination environment around the Re(I) may be described as a distorted octahedron in which the ligand behaves in a bidentate fashion through the nitrogen atom of the nitroso group and an adjacent carbonylic oxygen, making a five-membered chelate ring. The coordination sphere is completed with three carbonyl groups in fac-arrangement and one chlorine atom (DANTU complex) or water molecule (VIO complexes). The higher acidity of violuric acids, if compared with DANTU one, may explain both synergic deprotonation and chloride substitution in the [ReCl(CO)3]+ moiety to form the Re-violurato complexes.

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Enol nitrosation revisited: determining reactivity of ambident nucleophiles

Enols are one of the most Important types of ambident nucleophiles being widely used as reagents in organic chemistry, The relevance of enols has led to considerable interest in developing methods to determine the reactivity of their nucleophilic centers, In this sense, the mainstream, literature works on this topic make use of a. combination of overall rate constants together with the analysis of the reaction products, By knowing the product ratio it is possible to determine the ratio between the reaction rates on each site, Thus, the reactivity for each, nucleophilic position can be obtained, This is a reliable approach as long as the isolation or in situ characterization of the reaction products can be carried out, In the case of unstable and/or interconvertible products where the use of identification techniques is not possible, an alternative methodology must be found, For that: reason, our research group has developed a model that allows us to study and quantify separately the reaction rates of enol nucleophilic centers even if only one final reaction product is obtained, This model is based on the fact: that nitrosation of enols shows well-differentiated behavior depending on whether the reaction proceeds through the carbon or the oxygen atom, The present study provides insights into the ambident nature of enols as well as a methodology for determining the chemical reactivity of their nucleophilic centers.