2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride FAQ
2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride FAQ
2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride is a reactive uracil-derived sulfonyl chloride used as an electrophilic sulfonylating agent for the preparation of sulfonamides, sulfonate esters, and other sulfone-containing building blocks in medicinal and synthetic chemistry.
- Chemical Name
- 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride
- Common Synonym
- Uracil-5-sulfonyl chloride
- SKU
- D696629
- Functional Group
- Sulfonyl chloride (–SO₂Cl) on a pyrimidine-2,4(1H,3H)-dione scaffold
- Key Reactivity
- Reacts with amines to form sulfonamides; reacts with alcohols/phenols to form sulfonate esters; highly moisture-sensitive
- Storage Recommendation
- Store in a cool, dry, well-ventilated location, away from moisture; use under inert atmosphere when possible
What Is 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl Chloride?
2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride, commonly referred to as uracil-5-sulfonyl chloride, is a heterocyclic sulfonyl chloride in which the electrophilic –SO₂Cl group is installed at the 5-position of the uracil (pyrimidine-2,4-dione) ring system. The compound combines the hydrogen-bonding and pharmacophoric features of the uracil scaffold with the high reactivity of a sulfonyl chloride electrophile, making it a versatile bifunctional building block.
Because the sulfonyl chloride moiety is among the most reactive acylating-type electrophiles, this reagent enables rapid, high-yielding coupling reactions with nucleophiles under mild conditions, which is particularly attractive for fragment-based drug discovery and the synthesis of sulfonamide libraries targeting nucleobase-binding proteins.
Chemical Properties and Handling
As a sulfonyl chloride, this compound is highly susceptible to hydrolysis upon contact with moisture, generating the corresponding sulfonic acid (uracil-5-sulfonic acid) and hydrochloric acid. Researchers should therefore handle it under anhydrous conditions, preferably under an inert atmosphere of nitrogen or argon. Solvents such as dry dichloromethane, acetonitrile, or tetrahydrofuran are commonly employed.
The compound liberates HCl during reactions with amines or alcohols; an external base such as triethylamine or pyridine is typically added to neutralize the acid and prevent protonation of the nucleophile. Personal protective equipment including chemical-resistant gloves, eye protection, and a lab coat must be worn, and reactions should be performed in a fume hood to avoid inhalation of HCl vapour.
Synthetic Applications
The primary application of 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride is the preparation of uracil-5-sulfonamides through reaction with primary or secondary amines. Sulfonamides derived from uracil are of interest in medicinal chemistry because the uracil ring can engage in specific interactions with enzyme active sites that recognise nucleobases or nucleotides.
Additional uses include the synthesis of sulfonate esters via reaction with phenols or aliphatic alcohols, and the preparation of sulfonyl fluorides through halogen exchange (SuFEx chemistry). The compound may also serve as a precursor to uracil-5-sulfinic acid derivatives under reductive conditions. Overall, it provides a convenient single-step route to a wide range of sulfone-containing nucleobase analogues that would otherwise require multi-step synthesis.
Storage, Stability, and Quality
To maintain reagent integrity, 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride should be stored in a tightly sealed container in a cool, dry environment away from moisture and incompatible materials such as bases, alcohols, and water. Refrigerated storage (2–8 °C) under an inert gas blanket is recommended for long-term preservation.
Aladdin Scientific supplies this compound (SKU D696629) with a certificate of analysis confirming identity and purity. Researchers requiring specific purity data or analytical documentation should contact Aladdin Technical Support or refer to the product's certificate of analysis available on the product page.
Ordering and Availability
2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride is available from Aladdin Scientific under SKU D696629. To place an order, visit the Aladdin Scientific website and search by SKU or chemical name, or contact your regional Aladdin sales representative. Bulk quantities and custom packaging may be available upon request.
For questions about pricing, lead times, export restrictions, or technical specifications, please reach out to Aladdin customer service. Researchers can also request a safety data sheet (SDS) and certificate of analysis directly from the product page.
Frequently asked questions
What nucleophiles react with 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride?
Primary and secondary amines react readily to give sulfonamides, which are the most common target products. Phenols and aliphatic alcohols can be sulfonylated to afford sulfonate esters, while fluoride sources under SuFEx conditions can convert the sulfonyl chloride to the corresponding sulfonyl fluoride.
Why is moisture control critical when working with this sulfonyl chloride?
The –SO₂Cl group hydrolyses rapidly in the presence of water to produce uracil-5-sulfonic acid and HCl, rendering the reagent inactive before it can react with the intended nucleophile. Working under anhydrous conditions with dry solvents and an inert atmosphere preserves reagent activity and maximises reaction yield.
Do I need an external base when performing sulfonamide synthesis with this reagent?
Yes. Each equivalent of sulfonyl chloride reacts with one equivalent of amine to release one equivalent of HCl. Without a base, this acid can protonate the amine nucleophile and slow or stop the reaction. A tertiary amine base such as triethylamine or Hünig's base (DIPEA) is typically added in slight excess to scavenge HCl and maintain reactivity.
How should I confirm the identity and purity of SKU D696629 upon receipt?
Aladdin Scientific provides a certificate of analysis (CoA) with each lot, which includes identity confirmation (typically by NMR or HPLC) and purity data. You can download the CoA from the product page on the Aladdin Scientific website or contact customer service to request it directly.
What solvents are recommended for reactions involving this compound?
Dry aprotic solvents are preferred, including anhydrous dichloromethane, acetonitrile, and tetrahydrofuran. Protic solvents and solvents containing residual water should be avoided because they promote hydrolysis of the sulfonyl chloride before the desired reaction can proceed.
References
- General reactivity of sulfonyl chlorides as electrophilic sulfonylating agents — textbook-level knowledge; no specific primary reference cited.
- SuFEx click chemistry involving sulfonyl fluorides and sulfonyl chlorides — general field knowledge attributed to Sharpless and coworkers; specific citation not confirmed from source material.
- Aladdin Scientific product page for D696629 — 2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-sulfonyl chloride.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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