1,3-Dimethyluracil-5-carboxaldehyde
[CAS# 4869-46-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Urinary (urea) pyrimidine
• Name: 1,3-Dimethyluracil-5-carboxaldehyde
• Molecular Formula: C₇H₈N₂O₃
• Molecular Weight: 168.15
• CAS Registry Number: 4869-46-9
• EC Number: 676-471-7
• SMILES: CN1C=C(C(=O)N(C1=O)C)C=O

Properties

• Solubility: 6901 mg/L (25 ºC water)
• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.611, Calc.^*
• Melting point: 135.86 ºC
• Boiling Point: 274.1±50.0 ºC (760 mmHg), Calc.^*, 365.12 ºC
• Flash Point: 122.6±22.5 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

1,3-Dimethyluracil-5-carboxaldehyde is a significant compound within the realm of organic chemistry and medicinal chemistry, primarily recognized for its diverse applications and potential therapeutic benefits. The substance is a derivative of uracil, a naturally occurring pyrimidine base found in nucleic acids. The discovery of 1,3-Dimethyluracil-5-carboxaldehyde can be traced back to the mid-20th century when researchers began exploring modified uracil compounds for their biological activities and potential pharmaceutical applications.

The chemical structure of 1,3-Dimethyluracil-5-carboxaldehyde features a uracil skeleton with two methyl groups at the 1 and 3 positions and an aldehyde group at the 5 position. This modification not only alters the compound's solubility and stability but also enhances its reactivity, making it a valuable precursor for further chemical transformations. The synthesis of 1,3-Dimethyluracil-5-carboxaldehyde typically involves multi-step organic reactions, including oxidation and condensation processes that enable the introduction of functional groups into the uracil framework.

One of the primary applications of 1,3-Dimethyluracil-5-carboxaldehyde lies in the field of medicinal chemistry, where it has been investigated for its antiviral properties. The compound has shown promise as a potential antiviral agent due to its ability to inhibit viral replication and affect viral polymerases. Studies have indicated that derivatives of 1,3-Dimethyluracil-5-carboxaldehyde can act against various viruses, including those that cause respiratory infections and other viral diseases. This has led to ongoing research into its efficacy and mechanisms of action, positioning the compound as a candidate for further development in antiviral therapeutics.

In addition to its antiviral properties, 1,3-Dimethyluracil-5-carboxaldehyde has been explored for its potential applications in cancer treatment. The compound has been shown to exhibit cytotoxic effects on certain cancer cell lines, prompting investigations into its mechanism of action and possible use in combination therapies. The ability to selectively target cancer cells while minimizing harm to healthy cells is a key focus of current cancer research, and compounds like 1,3-Dimethyluracil-5-carboxaldehyde contribute valuable insights into this pursuit.

Moreover, 1,3-Dimethyluracil-5-carboxaldehyde serves as a versatile building block in organic synthesis. Its unique functional groups allow it to participate in various chemical reactions, enabling the creation of more complex molecules. This versatility makes it an essential compound in the development of new materials and pharmaceuticals, contributing to advancements in drug discovery and formulation.

The compound also finds utility in the field of biochemistry, where it may be used as a biochemical probe to study enzyme activities related to nucleic acid metabolism. Understanding how such compounds interact with enzymes involved in nucleotide synthesis and degradation can provide valuable insights into cellular processes and potential therapeutic targets.

Safety considerations are paramount in the handling and use of 1,3-Dimethyluracil-5-carboxaldehyde. Appropriate safety measures should be in place to minimize exposure, and research involving the compound should adhere to regulatory guidelines governing the use of chemical substances in laboratories and pharmaceutical applications.

In summary, 1,3-Dimethyluracil-5-carboxaldehyde is a compound of significant interest in the fields of medicinal chemistry and organic synthesis. Its discovery has opened avenues for research into antiviral and anticancer therapies, while its versatility in organic synthesis underscores its importance in the development of novel materials and pharmaceuticals. Ongoing research into the compound's properties and potential applications continues to contribute to advancements in various scientific disciplines.