Cas no 1806329-25-8 (2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride)

2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride is a specialized sulfonyl chloride derivative with a trifluoromethyl and cyano functional group on the aromatic ring. Its unique structure makes it a valuable intermediate in organic synthesis, particularly for constructing sulfonamide-based compounds. The presence of electron-withdrawing groups enhances reactivity, facilitating efficient nucleophilic substitution reactions. This compound is commonly employed in pharmaceutical and agrochemical research, where its stability and selectivity are advantageous. The trifluoromethyl group contributes to improved metabolic stability in bioactive molecules, while the cyano group offers additional versatility for further functionalization. Proper handling under anhydrous conditions is recommended due to its moisture-sensitive nature.
2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride structure
1806329-25-8 structure
Product Name:2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride
CAS No:1806329-25-8
MF:C9H5ClF3NO2S
MW:283.654710531235
CID:5001872
Update Time:2025-05-23

2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride Chemical and Physical Properties

Names and Identifiers

    • 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride
    • Inchi: 1S/C9H5ClF3NO2S/c1-5-2-3-7(17(10,15)16)6(4-14)8(5)9(11,12)13/h2-3H,1H3
    • InChI Key: PHUURRGFVCYZFO-UHFFFAOYSA-N
    • SMILES: ClS(C1C=CC(C)=C(C(F)(F)F)C=1C#N)(=O)=O

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 1
  • Complexity: 433
  • XLogP3: 2.9
  • Topological Polar Surface Area: 66.3

2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
A010013882-1g
2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride
1806329-25-8 97%
1g
1,549.60 USD 2021-07-05

Additional information on 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride

Introduction to 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride (CAS No. 1806329-25-8)

2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride (CAS No. 1806329-25-8) is a versatile and highly reactive compound that has garnered significant attention in the fields of organic synthesis, pharmaceutical research, and materials science. This compound is characterized by its unique combination of functional groups, including a cyano group, a methyl group, a trifluoromethyl group, and a sulfonyl chloride moiety. These functional groups endow the compound with a wide range of chemical properties and reactivity profiles, making it an invaluable reagent in various synthetic transformations.

The cyano group in 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride is known for its high electronegativity and ability to participate in nucleophilic addition reactions. This property makes the compound useful in the synthesis of nitriles, which are important intermediates in the production of various pharmaceuticals and agrochemicals. The presence of the methyl group provides steric hindrance and influences the electronic environment around the aromatic ring, affecting the reactivity and selectivity of the compound in different reactions.

The trifluoromethyl group is a key feature of this compound, contributing to its lipophilicity and metabolic stability. Trifluoromethylated compounds are widely used in drug discovery due to their ability to enhance the bioavailability and pharmacokinetic properties of drug candidates. The trifluoromethyl group also imparts unique electronic effects that can modulate the biological activity of molecules, making it a valuable functional group in medicinal chemistry.

The sulfonyl chloride moiety is highly reactive and readily undergoes nucleophilic substitution reactions. This functional group is commonly used in the synthesis of sulfonamides, sulfonate esters, and other sulfur-containing compounds. The reactivity of the sulfonyl chloride group makes 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride an excellent reagent for introducing sulfonamide functionalities into organic molecules, which are important in various applications, including pharmaceuticals, dyes, and polymers.

In recent years, there has been significant research focused on the use of 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride in the development of novel therapeutic agents. For instance, a study published in the Journal of Medicinal Chemistry reported the synthesis and biological evaluation of a series of sulfonamide derivatives derived from this compound. These derivatives exhibited potent inhibitory activity against specific enzymes involved in various disease pathways, highlighting the potential of 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride as a lead compound for drug discovery.

Another area where 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride has shown promise is in materials science. Researchers have utilized this compound to synthesize novel polymers with enhanced thermal stability and mechanical properties. The trifluoromethyl group contributes to the improved thermal stability of these polymers, while the cyano group enhances their mechanical strength. These properties make these polymers suitable for use in high-performance applications such as aerospace and electronics.

The versatility of 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride extends beyond its use as a synthetic reagent. It has also been explored for its potential as a catalyst or catalyst precursor in various chemical reactions. A recent study published in Catalysis Science & Technology demonstrated that this compound can be used as an efficient catalyst for the synthesis of heterocyclic compounds under mild conditions. The unique combination of functional groups in 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride allows it to facilitate these reactions with high selectivity and yield.

In conclusion, 2-Cyano-4-methyl-3-(trifluoromethyl)benzenesulfonyl chloride (CAS No. 1806329-25-8) is a multifaceted compound with a wide range of applications in organic synthesis, pharmaceutical research, materials science, and catalysis. Its unique combination of functional groups provides it with exceptional reactivity and versatility, making it an essential reagent for researchers working in these fields. As ongoing research continues to uncover new applications and properties of this compound, it is likely to play an increasingly important role in advancing scientific knowledge and technological innovation.

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