Cas no 24590-55-4 (N,N-bis(2-chloroethyl)sulfamoyl chloride)

N,N-bis(2-chloroethyl)sulfamoyl chloride is a reactive sulfonyl chloride derivative primarily used as an intermediate in organic synthesis. Its key advantages include its bifunctional reactivity, enabling the introduction of both sulfamoyl and chloroethyl groups into target molecules. This compound is particularly valuable in the preparation of alkylating agents and sulfonamide-based pharmaceuticals. The presence of two chloroethyl groups enhances its utility in crosslinking applications, making it suitable for modifying polymers or biomolecules. It exhibits high electrophilicity, facilitating efficient nucleophilic substitution reactions. Proper handling under inert conditions is recommended due to its moisture sensitivity. The compound’s versatility makes it a useful building block in medicinal chemistry and materials science.
N,N-bis(2-chloroethyl)sulfamoyl chloride structure
24590-55-4 structure
Product Name:N,N-bis(2-chloroethyl)sulfamoyl chloride
CAS No:24590-55-4
MF:C4H8Cl3NO2S
MW:240.535817146301
CID:278700
PubChem ID:212596
Update Time:2025-05-25

N,N-bis(2-chloroethyl)sulfamoyl chloride Chemical and Physical Properties

Names and Identifiers

    • Sulfamoyl chloride,N,N-bis(2-chloroethyl)-
    • N.N-Di-(2-chlorethyl)-sulfaminsaeurechlorid
    • N,N-bis(2-chloroethyl)sulfamoyl chloride
    • N,N-Bis-(2-chloraethyl)-sulfamidsaurechlorid
    • 24590-55-4
    • BRN 2249509
    • N,N-Bis-(2-chloraethyl)-sulfamidsaurechlorid [German]
    • DTXSID70947478
    • AKOS006333950
    • Sulfamoyl chloride, N,N-bis(2-chloroethyl)-
    • bis(2-chloroethyl)sulfamyl chloride
    • EN300-1612253
    • Inchi: 1S/C4H8Cl3NO2S/c5-1-3-8(4-2-6)11(7,9)10/h1-4H2
    • InChI Key: VLCSGRLLYBKYGG-UHFFFAOYSA-N
    • SMILES: ClS(N(CCCl)CCCl)(=O)=O

Computed Properties

  • Exact Mass: 238.93434
  • Monoisotopic Mass: 238.934
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 5
  • Complexity: 182
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.5
  • Topological Polar Surface Area: 45.8?2

Experimental Properties

  • Density: 1.532
  • Boiling Point: 322.7°Cat760mmHg
  • Flash Point: 148.9°C
  • Refractive Index: 1.52
  • PSA: 37.38

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Additional information on N,N-bis(2-chloroethyl)sulfamoyl chloride

N,N-Bis(2-Chloroethyl)Sulfamoyl Chloride: A Comprehensive Overview

N,N-Bis(2-chloroethyl)sulfamoyl chloride, also known by its CAS number 24590-55-4, is a chemical compound with significant applications in various industries. This compound is a derivative of sulfamoyl chloride, where the sulfonamide group is substituted with two chloroethyl groups. The molecular formula of this compound is C6H8Cl3NO2, and its molecular weight is approximately 197.56 g/mol. The compound exists as a colorless to pale yellow liquid, and it is highly reactive due to the presence of the chloroethyl groups and the sulfonamide moiety.

The synthesis of N,N-bis(2-chloroethyl)sulfamoyl chloride involves the reaction of sulfamoyl chloride with 2-chloroethanol in the presence of a base such as pyridine. This reaction typically occurs under controlled conditions to ensure optimal yield and purity. The compound is widely used as an intermediate in organic synthesis, particularly in the preparation of various pharmaceuticals, agrochemicals, and specialty chemicals.

In recent years, there has been growing interest in the application of N,N-bis(2-chloroethyl)sulfamoyl chloride in the development of new drug delivery systems. Researchers have explored its potential as a building block for creating bioactive molecules with enhanced pharmacokinetic properties. For instance, studies have shown that this compound can be used to synthesize prodrugs that exhibit improved solubility and bioavailability.

The reactivity of N,N-bis(2-chloroethyl)sulfamoyl chloride makes it an ideal candidate for nucleophilic substitution reactions. In such reactions, the chlorides can be replaced by various nucleophiles, leading to the formation of diverse derivatives. This versatility has made it a valuable reagent in medicinal chemistry, where it is often used to modify existing drug molecules to improve their therapeutic efficacy.

From an environmental perspective, understanding the degradation pathways of N,N-bis(2-chloroethyl)sulfamoyl chloride is crucial for assessing its potential impact on ecosystems. Recent studies have focused on its biodegradation under aerobic and anaerobic conditions, as well as its fate in aquatic environments. These studies have provided valuable insights into the compound's persistence and toxicity, which are essential for regulatory assessments.

In conclusion, N,N-bis(2-chloroethyl)sulfamoyl chloride (CAS No. 24590-55-4) is a versatile and important chemical compound with a wide range of applications in organic synthesis and drug development. Its unique reactivity and structural properties make it a valuable tool for researchers and industry professionals alike. As ongoing research continues to uncover new applications and improve our understanding of its behavior, this compound will undoubtedly remain a key player in the field of chemical synthesis.

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