Chemical Identity and Physical Properties

4,6-Dimethyl-2-(methylsulfonyl)pyrimidine (CAS 19269-28-4; SKU D155140) is a six-membered nitrogen heterocycle bearing two ring nitrogen atoms at positions 1 and 3, methyl substituents at positions 4 and 6, and a methylsulfonyl group (–SO₂CH₃) at position 2. Its molecular formula is C₇H₁₀N₂O₂S with a molecular weight of 186.23 g/mol.

The compound typically presents as a white to off-white crystalline solid at room temperature. The electron-withdrawing sulfonyl moiety, flanked by the two ring nitrogen atoms, renders C-2 highly electrophilic, making the methylsulfonyl group an excellent leaving group in nucleophilic aromatic substitution reactions. The two methyl groups at C-4 and C-6 contribute steric and electronic modulation of ring reactivity and can themselves serve as handles for further functionalization via benzylic deprotonation or oxidation.

Note: Precise melting point, boiling point, solubility data, and appearance specifications should be confirmed from the Aladdin Scientific certificate of analysis (CoA) supplied with SKU D155140, as these values may vary by lot.

Synthetic Applications and Reactivity

The primary synthetic value of 4,6-Dimethyl-2-(methylsulfonyl)pyrimidine lies in its role as an activated electrophilic pyrimidine in nucleophilic aromatic substitution (SNAr). The –SO₂CH₃ group at C-2 is activated by the flanking ring nitrogens and departs as methanesulfinate upon reaction with nucleophiles. This strategy is widely applied in the preparation of:

• 2-Aminopyrimidines: Reaction with primary or secondary amines under mild conditions affords 2-amino-4,6-dimethylpyrimidine derivatives, key scaffolds in kinase inhibitor design and antimicrobial research.
• 2-Alkoxy- and 2-aryloxypyrimidines: Alkoxide or phenoxide nucleophiles displace the sulfonyl group to give ether-linked pyrimidine products relevant to agrochemical and pharmaceutical programs.
• C–C Bond Formation: Stabilised carbanions (e.g., malonates, active methylene compounds) can attack C-2, enabling carbon–carbon bond formation for complex molecule synthesis.

Additionally, the methyl groups at C-4 and C-6 can be exploited for Knoevenagel-type condensations or directed metalation strategies, expanding the utility of this scaffold beyond simple SNAr chemistry.

Review flag: Specific reaction conditions (temperature, solvent, base, yield data) cited above are based on general textbook knowledge of activated pyrimidine SNAr chemistry. Researchers should consult primary literature for optimised protocols for specific transformations.

Safe Handling, Storage, and Disposal

Personal Protective Equipment (PPE): Handle 4,6-Dimethyl-2-(methylsulfonyl)pyrimidine wearing appropriate nitrile gloves, safety glasses or goggles, and a laboratory coat. Where dust or aerosols may be generated, use a half-face respirator with an appropriate particulate filter or work in a fume hood.

Storage: Store the compound in a tightly sealed container in a cool (15–25 °C), dry, well-ventilated area away from strong oxidising agents, strong acids, and moisture. Keep away from sources of ignition. Verify recommended storage temperature range on the CoA or product label supplied with SKU D155140.

Stability: The compound is expected to be stable under recommended storage conditions; however, prolonged exposure to moisture or high humidity may cause hydrolysis of the sulfonyl group or other degradation. Confirm stability data from the CoA.

Spill Management: Collect solid spills using non-sparking tools into a suitable, labelled waste container. Avoid generating dust. Prevent contamination of drains and waterways.

Disposal: Dispose of in accordance with local, regional, and national chemical waste regulations. Do not dispose of via municipal sewage. Consult your institution's Environmental Health and Safety (EHS) office for guidance.

Note: Always consult the current Safety Data Sheet (SDS) for SKU D155140 before use. Specific hazard classifications, GHS pictograms, and first-aid measures are detailed therein.

Quality, Purity, and Procurement Guidance

For research applications demanding high reproducibility—such as medicinal chemistry lead optimisation, structure–activity relationship (SAR) studies, or reference standard preparation—the purity of 4,6-Dimethyl-2-(methylsulfonyl)pyrimidine is critical. Aladdin Scientific supplies SKU D155140 with lot-specific certificates of analysis (CoA) detailing purity determination methods (typically HPLC or GC), appearance, and identity confirmation (e.g., NMR, MS).

Procurement checklist for laboratory managers:

• Request a CoA and, where required, an SDS before placing an order.
• Confirm purity specification meets your assay threshold (commonly ≥97% or ≥98% for synthetic applications).
• Verify packaging size options (milligram to gram scale) available for SKU D155140 to match consumption and minimise freeze–thaw or open-container cycles.
• For regulated research environments, confirm compliance documentation requirements with Aladdin Scientific customer service.

Note: Specific purity grades and available pack sizes should be confirmed directly on the Aladdin Scientific product page for SKU D155140 or by contacting customer support, as these may be updated.