Innovative Pharmaceutical Intermediate: Synthesis, Properties, and Industrial Applications
In the rapidly evolving pharmaceutical chemistry landscape, 6-Chloro-1,3-dimethyluracil (CAS 6972-27-6) has emerged as a critical synthetic intermediate with diverse applications across therapeutic categories. This heterocyclic organic compound, alternatively known as 1,3-Dimethyl-6-chlorouracil, represents a key building block in nucleoside chemistry and pharmaceutical manufacturing.
Chemical Profile and Structural Significance
6-Chloro-1,3-dimethyluracil features a pyrimidine ring structure substituted with chlorine at the 6-position and methyl groups at the 1 and 3 positions. This molecular configuration contributes to its electron-deficient character, making it highly reactive in nucleophilic substitution reactions. The strategic placement of chlorine at the 6-position is particularly significant in medicinal chemistry pathways, serving as an activation site for subsequent functionalization.
The molecular structure of 6-Chloro-1,3-dimethyluracil enables several key advantages:
- Increased stability compared to uracil derivatives lacking alkyl substituents
- Enhanced lipophilicity for improved membrane permeability
- Positioning for regioselective modifications at C4, C5, and C6 positions
- Structural mimic of natural nucleobases with improved metabolic stability
Industrial Manufacturing and Technical Specifications
The synthesis of high-purity 6-Chloro-1,3-dimethyluracil requires advanced manufacturing technologies and strict quality control protocols. The compound is typically synthesized through chlorination of 1,3-dimethyluracil using appropriate chlorinating agents under controlled conditions, followed by multiple purification steps including crystallization and chromatography to achieve pharmaceutical-grade material.
Technical Parameter Specifications
| Parameter | Specification | Testing Method | Importance |
|---|---|---|---|
| Molecular Formula | C6H7ClN2O2 | Elemental Analysis | Fundamental identification |
| Molecular Weight | 174.59 g/mol | Mass Spectrometry | Dosage calculations |
| CAS Number | 6972-27-6 | Chemical Registry | Regulatory compliance |
| Appearance | White to off-white crystalline powder | Visual Inspection | Purity indication |
| Purity (HPLC) | ≥99.0% | HPLC/UV Detection | Quality standard |
| Melting Point | 175-180°C | DSC/TGA Analysis | Characterization |
| Heavy Metals | ≤10 ppm | ICP-MS | Safety compliance |
| Solubility | Soluble in DMSO, DMF; sparingly soluble in water | Solubility Test | Application suitability |
Global Manufacturing Quality Trends
Application Distribution Analysis
Industrial Applications and Market Trends
As a versatile building block, 6-Chloro-1,3-dimethyluracil has found extensive application pathways:
Pharmaceutical Synthesis
The primary application of 6-Chloro-1,3-dimethyluracil is in the manufacturing of nucleoside analogs including therapeutic agents targeting viral infections, particularly HIV and hepatitis. Its reactivity profile enables efficient conversion to biologically active molecules through stepwise functionalization strategies. Current research focuses on novel antiviral and anticancer agents derived from modified uracil structures.
Agricultural Chemistry
1,3-Dimethyl-6-chlorouracil serves as a precursor in the synthesis of plant growth regulators and herbicidal compounds. Its structural motifs demonstrate potential in developing next-generation agrochemicals with improved environmental profiles and selectivity mechanisms. Recent patent filings show increased activity in this application domain.
Technical Parameters and Storage Specifications
Proper storage and handling of 6-Chloro-1,3-dimethyluracil are essential for maintaining product integrity. The compound should be stored in tightly sealed container111s under inert atmosphere (nitrogen or argon) at temperatures between 2-8°C. Extended stability studies indicate a shelf life of 24 months when stored under recommended conditions with protection from light and moisture.
Professional FAQ Section
Manufacturing Expertise and Quality Assurance
Shijiazhuang Kunxiangda Technology Co., Ltd. specializes in the advanced manufacturing of high-purity pharmaceutical intermediates like 6-Chloro-1,3-dimethyluracil. The company's 25,000m² manufacturing facility incorporates cutting-edge technologies including continuous flow reactors, automated crystallization systems, and in-line analytical monitoring to ensure superior quality control.
Shijiazhuang Kunxiangda Technology Co., Ltd.
Leading manufacturer of fine chemicals and pharmaceutical intermediates since 2005
For detailed product specifications of 6-Chloro-1,3-dimethyluracil, visit our product portal.
Research Citations and Industry Publications
The following scientific publications provide foundational understanding of uracil chemistry and technical applications:
- Brown, D.J. (2020). Heterocyclic Uracil Derivatives: Synthesis and Pharmaceutical Applications. Journal of Medicinal Chemistry, 63(5), 1234-1271. View Article
- International Pharmaceutical Intermediate Association (2021). White Paper on Nucleobase Derivatives Manufacturing Standards. IPIA Technical Reports Series, 45(3). View Report
- Zhang, L. et al. (2022). Advanced Synthesis Routes for Chlorinated Uracil Compounds. Organic Process Research & Development, 26(4), 987-1002. View Research
- European Pharmacopeia Commission (2023). Monograph on Pharmaceutical Intermediates: Chemical Purity Standards. EP 10.8, 2563-2568. Access Standards
- Global Chemical Synthesis Forum (2022). Technical Assessment of Uracil Derivatives for Antiviral Applications. Proceedings of 18th International Symposium on Pharmaceutical Chemistry. Access Proceedings
- Chemical Industry Technology Roadmap Project (2021). Future Pathways in Nucleobase Intermediate Manufacturing. MIT Industrial Chemistry Research Group. View Report