4-Chloro-2-(methylthio)pyrimidine-5-carbonyl Chloride FAQ
4-Chloro-2-(methylthio)pyrimidine-5-carbonyl Chloride FAQ
5-Pyrimidinecarbonyl chloride， 4-chloro-2-(methylthio)- is a bifunctional heterocyclic acyl chloride building block featuring both a reactive carbonyl chloride group and a displaceable ring chlorine, making it a versatile electrophilic intermediate for the construction of complex pyrimidine-containing molecules in medicinal and agricultural chemistry research.
- Product Name
- 5-Pyrimidinecarbonyl chloride, 4-chloro-2-(methylthio)-
- SKU
- P769872
- Supplier
- Aladdin Scientific
- Functional Groups
- Acyl chloride (–COCl), ring C–Cl, methylthio (–SCH₃)
- Core Scaffold
- Pyrimidine ring
- Primary Use
- Electrophilic acylation and nucleophilic aromatic substitution in heterocyclic synthesis
Chemical Identity and Structure
5-Pyrimidinecarbonyl chloride, 4-chloro-2-(methylthio)- is a substituted pyrimidine derivative carrying three distinct reactive or modifiable sites: (1) a carbonyl chloride (acyl chloride) at the 5-position, which is highly electrophilic and reacts readily with nucleophiles such as amines and alcohols; (2) a chlorine substituent at the 4-position of the pyrimidine ring, susceptible to nucleophilic aromatic substitution (SNAr); and (3) a methylthio group at the 2-position, which can serve as a leaving group or be retained as a sulfur handle for further functionalization.
This combination of functionalities makes the compound a valuable bifunctional building block in medicinal chemistry, enabling orthogonal reactivity at two independent sites within a single synthetic step or sequence.
Handling, Safety, and Storage
As an acyl chloride, 5-Pyrimidinecarbonyl chloride, 4-chloro-2-(methylthio)- is moisture-sensitive and hydrolyzes upon contact with water or atmospheric humidity to generate hydrogen chloride (HCl) gas and the corresponding carboxylic acid. All handling should be performed under anhydrous conditions using dry glassware, inert-atmosphere techniques (nitrogen or argon), and appropriate personal protective equipment including chemical-resistant gloves, eye protection, and a lab coat.
The compound should be stored in a tightly sealed container under an inert atmosphere in a cool, dry environment away from moisture and incompatible materials such as bases, alcohols, and water. Refer to the Safety Data Sheet (SDS) provided by Aladdin Scientific for specific hazard classifications, first-aid measures, and disposal requirements before use.
Synthetic Applications and Reactivity
The acyl chloride functionality at the 5-position is the most reactive site and is commonly exploited for amide bond formation with primary or secondary amines, or ester formation with alcohols, typically in the presence of a base such as triethylamine to scavenge the liberated HCl. These reactions are generally performed in aprotic solvents such as dichloromethane, tetrahydrofuran, or acetonitrile at low to ambient temperatures.
The 4-chloro substituent on the pyrimidine ring undergoes nucleophilic aromatic substitution with amines, thiols, or alkoxides, often facilitated by mild heating or by the electron-withdrawing effect of the adjacent carbonyl and the methylthio-pyrimidine scaffold. The 2-methylthio group can be oxidized to a sulfoxide or sulfone to enhance ring electrophilicity, or displaced by amines under appropriate conditions, providing additional diversity for library synthesis in drug discovery programs.
Quality, Purity, and Ordering Information
Aladdin Scientific supplies 5-Pyrimidinecarbonyl chloride, 4-chloro-2-(methylthio)- under SKU P769872. Researchers requiring purity specifications, certificate of analysis (CoA), or Safety Data Sheet (SDS) documentation should contact Aladdin Scientific directly or visit the product page on the Aladdin Scientific website. Purity data, batch-specific analytical results, and available pack sizes are detailed in the accompanying CoA for each lot.
When placing an order, please reference SKU P769872 to ensure the correct product and specification are selected. For bulk quantities or custom packaging, contact the Aladdin Scientific sales team for a quotation.
Frequently asked questions
What is 5-Pyrimidinecarbonyl chloride, 4-chloro-2-(methylthio)- used for?
This compound is primarily used as a bifunctional building block in organic and medicinal chemistry. The acyl chloride group enables rapid amide or ester bond formation, while the 4-chloro substituent on the pyrimidine ring can undergo nucleophilic aromatic substitution, allowing two orthogonal functionalization reactions on a single scaffold.
How should I store 5-Pyrimidinecarbonyl chloride, 4-chloro-2-(methylthio)- (P769872)?
The compound should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) in a cool, dry location, away from moisture, water, alcohols, and bases. As an acyl chloride, it is sensitive to hydrolysis upon exposure to atmospheric humidity. Always consult the Aladdin Scientific SDS for full storage and handling requirements.
What precautions should I take when handling this acyl chloride in the laboratory?
Handle the compound in a well-ventilated fume hood using dry glassware and inert-atmosphere techniques to prevent moisture contact. Wear appropriate PPE including chemical-resistant gloves, safety goggles, and a lab coat. HCl gas is released upon hydrolysis, so avoid inhalation. Refer to the SDS for detailed hazard information and first-aid measures.
Can the 2-methylthio group be further functionalized?
Yes. The 2-methylthio group can be oxidized to a methylsulfinyl or methylsulfonyl group to increase the electrophilicity of the pyrimidine ring, thereby facilitating nucleophilic aromatic substitution at the 2-position. It can also be displaced directly by nitrogen or oxygen nucleophiles under suitable conditions, expanding the structural diversity achievable from this building block.
How do I obtain a Certificate of Analysis or Safety Data Sheet for P769872?
Certificates of Analysis and Safety Data Sheets for SKU P769872 are available through the Aladdin Scientific website on the product page, or by contacting Aladdin Scientific customer service directly. Please have your lot number ready when requesting batch-specific documentation.
References
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for acyl chloride reactivity and nucleophilic aromatic substitution.)
- Aladdin Scientific Product Page for SKU P769872: 5-Pyrimidinecarbonyl chloride, 4-chloro-2-(methylthio)-. Aladdin Scientific, Shanghai.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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