Cas no 1339325-76-6 (N,N-bis(cyclopropylmethyl)sulfamoyl chloride)

N,N-bis(cyclopropylmethyl)sulfamoyl chloride is a specialized sulfamoyl chloride derivative featuring cyclopropylmethyl substituents on the nitrogen atoms. This compound is primarily utilized as a key intermediate in organic synthesis, particularly in the preparation of sulfonamide-based compounds. Its cyclopropylmethyl groups confer enhanced steric and electronic properties, which can influence reactivity and selectivity in subsequent transformations. The sulfamoyl chloride moiety serves as a versatile electrophile, enabling efficient incorporation into target molecules under controlled conditions. Suitable for use in pharmaceutical and agrochemical research, this reagent offers precise functionalization opportunities while maintaining stability under standard handling protocols. Proper storage under inert conditions is recommended to preserve its reactivity.
N,N-bis(cyclopropylmethyl)sulfamoyl chloride structure
1339325-76-6 structure
Product Name:N,N-bis(cyclopropylmethyl)sulfamoyl chloride
CAS No:1339325-76-6
MF:C8H14ClNO2S
MW:223.72026014328
CID:5207837
PubChem ID:64214050
Update Time:2025-06-15

N,N-bis(cyclopropylmethyl)sulfamoyl chloride Chemical and Physical Properties

Names and Identifiers

    • Bis(cyclopropylmethyl)sulfamoyl chloride
    • N,N-bis(cyclopropylmethyl)sulfamoyl chloride
    • Inchi: 1S/C8H14ClNO2S/c9-13(11,12)10(5-7-1-2-7)6-8-3-4-8/h7-8H,1-6H2
    • InChI Key: IRXNNIFABBYASW-UHFFFAOYSA-N
    • SMILES: ClS(N(CC1CC1)CC1CC1)(=O)=O

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 5
  • Complexity: 263
  • XLogP3: 1.8
  • Topological Polar Surface Area: 45.8

N,N-bis(cyclopropylmethyl)sulfamoyl chloride Pricemore >>

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Additional information on N,N-bis(cyclopropylmethyl)sulfamoyl chloride

Recent Advances in the Application of N,N-bis(cyclopropylmethyl)sulfamoyl chloride (CAS: 1339325-76-6) in Chemical Biology and Pharmaceutical Research

N,N-bis(cyclopropylmethyl)sulfamoyl chloride (CAS: 1339325-76-6) has recently emerged as a versatile reagent in chemical biology and pharmaceutical research. This sulfamoyl chloride derivative has garnered significant attention due to its unique reactivity profile and potential applications in drug discovery and development. Recent studies have explored its utility as a key intermediate in the synthesis of sulfonamide-based compounds, which are widely recognized for their pharmacological properties.

One of the most notable applications of N,N-bis(cyclopropylmethyl)sulfamoyl chloride is in the development of novel enzyme inhibitors. Researchers have successfully employed this compound in the synthesis of sulfonamide-containing inhibitors targeting various enzymes, including carbonic anhydrases and proteases. The cyclopropylmethyl groups confer enhanced lipophilicity and metabolic stability to the resulting compounds, making them promising candidates for further optimization.

In a recent study published in the Journal of Medicinal Chemistry, researchers utilized N,N-bis(cyclopropylmethyl)sulfamoyl chloride to develop a series of potent and selective inhibitors for a specific isoform of carbonic anhydrase implicated in certain cancers. The study demonstrated that the introduction of the cyclopropylmethyl groups significantly improved the pharmacokinetic properties of the inhibitors while maintaining their target affinity.

Another area of active research involves the use of N,N-bis(cyclopropylmethyl)sulfamoyl chloride in the synthesis of sulfonamide-based prodrugs. The compound's ability to react with various nucleophiles, including amines and alcohols, makes it particularly useful for constructing prodrug linkages that can be cleaved under specific physiological conditions. This approach has been applied to improve the bioavailability of poorly soluble drugs.

Recent synthetic methodology developments have also expanded the utility of N,N-bis(cyclopropylmethyl)sulfamoyl chloride. A 2023 publication in Organic Letters described a novel one-pot procedure for the preparation of unsymmetrical sulfamides using this reagent, offering improved yields and reduced purification steps compared to traditional methods. This advancement has important implications for the efficient synthesis of sulfamide-containing drug candidates.

From a safety and handling perspective, recent studies have provided more detailed information about the stability and storage conditions of N,N-bis(cyclopropylmethyl)sulfamoyl chloride. While the compound is generally stable under inert atmosphere at low temperatures, it has been shown to be moisture-sensitive, requiring careful handling in anhydrous conditions. These findings have important practical implications for researchers working with this reagent.

Looking forward, the unique properties of N,N-bis(cyclopropylmethyl)sulfamoyl chloride suggest continued relevance in pharmaceutical research. Its combination of reactivity and the steric/electronic effects imparted by the cyclopropylmethyl groups make it particularly valuable for the development of next-generation sulfonamide-based therapeutics. Ongoing research is exploring its potential in targeted protein degradation strategies and covalent inhibitor design, areas that are currently at the forefront of drug discovery.

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