CAS 2991507-62-9, Cat. No EN300-46605561
Reagent for chlorination
N-acetoxy-N-chloro-4-nitrobenzamide is a novel and efficient electrophilic chlorination reagent derived from anomeric amides, designed to exploit the unique reactivity of pyramidalized nitrogen1. This reagent enables regioselective and chemoselective chlorination of (hetero)arenes, offering a powerful tool for late-stage functionalization in complex synthetic sequences. Its high reactivity, scalability, and mild reaction conditions make it a valuable alternative to traditional chlorination methods. It demonstrates broad substrate compatibility, including sensitive functional groups like amines, sulfonamides, and tertiary alcohols. The reagent provides clean transformations with minimal byproducts, outperforming other halogenating agents like Palau'chlor and N-chlorosuccinimide in both yield and selectivity. The compound is a bench-stable solid that decomposes gradually under ambient conditions. It is best stored below 0°C to minimize degradation. This reagent is scalable for both batch and flow chemistry, with demonstrated success in gram- and decagram-scale chlorination reactions.
Synonyms: [chloro-(4-nitrobenzoyl)amino] acetate; N-acetoxy-N-chloro-4-nitrobenzamide
Selected publication
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Discovery of N–X Anomeric Amides as Electrophilic Halogenation Reagents.
Wang Y.; Bi C.; Kawamata Y.; Grant L.; Samp L.; Richardson P.; Zhang S.; Harper K.; Palkowitz M.; Vasilopoulos A.; Collins M.; Oderinde M.; Tyrol C.; Chen D.; LaChapelle E.; Bailey J.; Qiao J.; Baran P. Nat Chem 2024, 16 (9), 1539–1545. DOI: 10.1038/s41557-024-01539-4