Cas no 1216026-07-1 (6-fluoro-1H-indole-3-sulfonyl chloride)

6-Fluoro-1H-indole-3-sulfonyl chloride is a versatile sulfonylation reagent used in organic synthesis, particularly for introducing the 6-fluoroindole-3-sulfonyl moiety into target molecules. Its key advantages include high reactivity as an electrophile, enabling efficient sulfonamide bond formation with amines and other nucleophiles. The fluorine substituent enhances electronic properties, making it valuable for medicinal chemistry applications, such as the development of bioactive compounds. The compound is stable under controlled conditions and offers selectivity in reactions due to its distinct indole core. It is commonly employed in the synthesis of pharmaceuticals, agrochemicals, and advanced intermediates, where precise functionalization is critical. Proper handling under inert conditions is recommended due to its moisture sensitivity.
6-fluoro-1H-indole-3-sulfonyl chloride structure
1216026-07-1 structure
Product Name:6-fluoro-1H-indole-3-sulfonyl chloride
CAS No:1216026-07-1
MF:C8H5ClFNO2S
MW:233.647203207016
CID:2617693
PubChem ID:53438780
Update Time:2025-10-28

6-fluoro-1H-indole-3-sulfonyl chloride Chemical and Physical Properties

Names and Identifiers

    • 6-fluoro-1H-indole-3-sulfonyl chloride
    • AKOS006336055
    • DB-140647
    • EN300-368556
    • DTXSID40701504
    • SCHEMBL20355068
    • 1216026-07-1
    • Inchi: 1S/C8H5ClFNO2S/c9-14(12,13)8-4-11-7-3-5(10)1-2-6(7)8/h1-4,11H
    • InChI Key: JSTGPRSOPPQMDQ-UHFFFAOYSA-N
    • SMILES: ClS(C1=CNC2C=C(C=CC1=2)F)(=O)=O

Computed Properties

  • Exact Mass: 232.9713554g/mol
  • Monoisotopic Mass: 232.9713554g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 316
  • 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: 2.2
  • Topological Polar Surface Area: 58.3?2

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Additional information on 6-fluoro-1H-indole-3-sulfonyl chloride

6-Fluoro-1H-indole-3-sulfonyl chloride (CAS No. 1216026-07-1)

6-Fluoro-1H-indole-3-sulfonyl chloride, also known by its CAS number 1216026-07-1, is a highly reactive and versatile compound in the field of organic chemistry. This compound belongs to the family of sulfonyl chlorides, which are widely used as intermediates in the synthesis of various pharmaceuticals, agrochemicals, and advanced materials. The presence of the fluoro group at the 6-position of the indole ring introduces unique electronic and steric properties, making it a valuable building block for designing bioactive molecules.

The structure of 6-fluoro-1H-indole-3-sulfonyl chloride consists of an indole ring system with a sulfonyl chloride group attached at the 3-position and a fluorine atom at the 6-position. The indole moiety is a heterocyclic aromatic compound with significant biological activity, often found in natural products and synthetic drugs. The sulfonyl chloride group is highly electrophilic, making it an excellent leaving group in substitution reactions. This property enables the compound to participate in various nucleophilic aromatic substitutions, which are crucial in drug discovery and material synthesis.

Recent studies have highlighted the potential of 6-fluoro-1H-indole-3-sulfonyl chloride as a key intermediate in the development of kinase inhibitors, which are essential in targeting cancer cells. Researchers have demonstrated that the fluorine substituent at the 6-position enhances the compound's ability to bind to specific protein targets, thereby improving its bioavailability and efficacy. This finding has opened new avenues for exploring its applications in oncology and other therapeutic areas.

In addition to its role in drug discovery, 6-fluoro-1H-indole-3-sulfonyl chloride has been utilized in the synthesis of advanced materials such as conductive polymers and optoelectronic devices. The indole-based structure provides a platform for creating conjugated systems with tailored electronic properties. For instance, recent research has shown that incorporating this compound into polymer frameworks can significantly enhance their charge transport capabilities, making them suitable for use in organic light-emitting diodes (OLEDs) and flexible electronics.

The synthesis of 6-fluoro-1H-indole-3-sulfonyl chloride typically involves multi-step processes that require precise control over reaction conditions. One common approach involves the sulfonation of 6-fluoroindole followed by chlorination to introduce the sulfonyl chloride group. The reaction conditions, such as temperature, solvent, and catalyst selection, play a critical role in ensuring high yields and product purity. Researchers have optimized these conditions to achieve scalable production methods that meet industrial standards.

The application of 6-fluoro-1H-indole-3-sulfonyl chloride extends beyond traditional organic synthesis. It has been employed as a reagent in click chemistry, where it facilitates rapid and efficient bond formation between molecules. This capability has been leveraged in combinatorial chemistry to generate diverse libraries of compounds for high-throughput screening in drug discovery programs.

In conclusion, 6-fluoro-1H-indole-3-sulfonyl chloride (CAS No. 1216026-07-1) is a multifaceted compound with significant potential in various fields of science and technology. Its unique chemical properties, combined with recent advancements in synthetic methodologies and application areas, position it as an indispensable tool for researchers aiming to develop innovative solutions in medicine, materials science, and beyond.

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