1461-67-2

Basic information

• Product Name: 5-IODO-6-METHYLURACIL
• Synonyms: 5-IODO-6-METHYLURACIL;5-iodo-6-methyl-1H-pyrimidine-2,4-dione;5-iodo-6-MethylpyriMidine-2,4(1H,3H)-dione;5-iodo-6-MethylpyriMidine-2,4-diol
• CAS NO: 1461-67-2
• Molecular Formula: C₅H₅IN₂O₂
• Molecular Weight: 252.01
• Mol File: 1461-67-2.mol

Chemical Properties

• Melting Point: 280 °C (dec.)(lit.)
• Appearance: /
• Density: 2.17 g/cm³
• Refractive Index: 1.666
• Storage Temp.: -20°C
• PKA: 8.07±0.10(Predicted)
• CAS DataBase Reference: 5-IODO-6-METHYLURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-IODO-6-METHYLURACIL(1461-67-2)
• EPA Substance Registry System: 5-IODO-6-METHYLURACIL(1461-67-2)

Safety Data

• Hazard Codes: Xn
• Statements: 40-42/43
• Safety Statements: 22-26-36
• WGK Germany: 3
• Hazardous Substances Data: 1461-67-2(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
5-IODO-6-METHYLURACIL is used as a research compound for exploring its interactions with RNA and other biomolecules, potentially leading to a better understanding of RNA structure and function.
Used in Pharmaceutical Development:
As a derivative of uracil, 5-IODO-6-METHYLURACIL is used as a starting material or intermediate in the synthesis of novel pharmaceuticals, with the aim of developing new drugs that could target RNA-related diseases or processes.
Used in Laboratory Settings:
5-IODO-6-METHYLURACIL is used as a stable and easily handled chemical for educational purposes, allowing students and researchers to study its properties and behavior in various chemical reactions and experiments.

InChI:InChI=1/C5H5IN2O2/c1-2-3(6)4(9)8-5(10)7-2/h1H3,(H2,7,8,9,10)

Upstream product

• 626-48-2 2,4-dihydroxy-6-methylpyrimidine 
• 626-48-2 6-Methyluracil 

Downstream Products

• 134039-54-6 1,2,3,4-Tetrahydro-5-iodo-1,3,6-trimethyl-2,4-dioxopyrimidine 
• 1146966-39-3 C₂₃H₂₅IN₂O₅ 
• 1174267-63-0 1,3-dibenzyl-5-iodo-6-phenethyluracil 
• 15018-56-1 5-bromo-6-methyluracil 
• 62459-19-2 5,5-dibromo-6-hydroxy-6-methyl-5,6-dihydrouracil 

Relevant articles and documents

Oxidative halogenation of 6-methyluracil

An efficient method has been developed for the preparation of halo derivatives of 6-methyluracil by employing oxidative halogenation. Elemental halogens and potassium halides were used as the halogenating agents, while NaNO3 and H2O2 were used as the oxidizing agents. Iodination of 6-methyl-uracil leads to 5-iodo-6-methyluracil as the single reaction product, while bromination or chlorination lead to 5-halo-6-methyluracil, 5,5-dihalo-6-hydroxy-6-methyl-5,6-dihydrouracil, or their mixture depending on the acidity of the medium and the ratio of the substrate and reagents. Bromination of 5-chloro-6-methyluracil leads to 5-bromo-5-chloro-6-hydroxy-6-methyl-5,6-dihydrouracil, while chlorination of 6-methyl-, 5-bromo-6-methyl-, and 5-chloro-6-methyluracils using gaseous chlorine yields 5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil.

A DNA-Based Two-Component Excitonic Switch Utilizing High-Performance Diarylethenes

Nucleosidic diarylethenes (DAEs) are an emerging class of photochromes but have rarely been used in materials science. Here, we have developed doubly methylated DAEs derived from 2′-deoxyuridine with high thermal stability and fatigue resistance. These new photoswitches not only outperform their predecessors but also rival classical non-nucleosidic DAEs. To demonstrate the utility of these new DAEs, we have designed an all-optical excitonic switch consisting of two oligonucleotides: one strand containing a fluorogenic double-methylated 2′-deoxyuridine as a fluorescence donor and the other a tricyclic cytidine (tC) as acceptor, which together form a highly efficient conditional F?rster-Resonance-Energy-Transfer (FRET) pair. The system was operated in liquid and solid phases and showed both strong distance- and orientation-dependent photochromic FRET. The superior ON/OFF contrast was maintained over up to 100 switching cycles, with no detectable fatigue.

SULFONAMIDE DERIVATIVE AND PHARMACEUTICAL USE THEREOF

Provided is a sulfonamide derivative represented by the following general formula (1) and having an α4 integrin inhibitory effect with high selectivity with a low effect on α4β1 and a high effect on α4β7, or a pharmaceutically acceptable salt thereof (in the general formula (1), A, B, D, E, R41, and a to h are as described in the description).

PYRIMIDINE COMPOUNDS AS TUBERCULOSIS INHIBITORS

The present invention relates to compounds II useful as inhibitors of treating tuberculosis. The invention also provides processes for preparing compounds of the invention.

Facile alternative synthesis of 1-alkyl-5-alkylamino-6-phenethyluracils

A short alternative synthesis of 1-alkyl-5-alkylamino-6-phenethyluracil is described in 47% overall yield of 1a via five steps starting from commercially available 6-methyluracil.

A comparison of microwave-accelerated and conventionally heated iodination reactions of some arenes and heteroarenes, using ortho-periodic acid as the oxidant

A fast and simple method for the oxidative iodination of some activated arenes and heteroarenes, either under microwave irradiation or by conventional heating, is reported, using diiodine and ortho-periodic acid as the oxidant. The reactions were carried out in hot 95% ethanol under a reflux condenser. For the microwave assisted reactions, the reaction times were always notably shortened, but the yields were nearly the same as those afforded by the conventional method.

The supramolecular structure of 5-Iodo-6-methyluracil

5-Iodo-6-methyluracil crystals were studied by X-ray diffraction; the crystals were isolated from an aqueous solution at pH 5.5. The elementary unit in the structure of 5-iodo-6-methyluracil was found to be a pseudocentrosymmetrical H-dimer of type k. Subsequent self-assemblage of H-dimers results in the formation of strongly corrugated layers whose outside surface is formed by methyl groups and iodine atoms. 5-Iodo-6-methyluracil molecules have two H-bond recognition centers, one of which participates in the formation of H-dimers, and the other, in their association to layers through the formation of H-bonds with water molecules. Such a layer structure has not been observed earlier for uracil derivatives. Copyright

Hypervalent iodine in synthesis 91: A mild and efficient method for the halogenation of 6-methyluracil derivatives

The combined reagent of iodobenzene diacetate (or polymer-supported iodobenzene diacetate) with iodine or bromine was used as an effective halogenative agent of 6-methyluracil derivatives to the corresponding 5-halo-6-methyluracil derivatives at room temperature with high yields.