N-(4-(2-Chloroacetyl)phenyl)methanesulfonamide (CAS 64488-52-4) is an alpha-chloroketone sulfonamide of the chloroacetylphenyl-methanesulfonamide chemical class. This electrophilic intermediate is an important part of making a lot of APIs that contain sulfonamides. For example, it is an important step in making Sotalol and other beta-adrenergic blocking agents that have the phenylmethanesulfonamide pharmacophore. The alpha-halo ketone (chloroacetyl) is a reactive electrophile that can be used in nucleophilic substitution with amines (Darzens, N-alkylation) to add the aminoalcohol side chain that is found in beta-blockers and antiarrhythmics. Because ICH M7 genotoxic impurity assessment is needed for reactive alpha-haloketones, this class of compounds often has positive Ames test results because they can alkylate other compounds.
ApiSyn offers N-(4-(2-Chloroacetyl)phenyl)methanesulfonamide (CAS 64488-52-4) as a pharmaceutical synthetic intermediate and ICH M7 mutagenic impurity reference standard for the development of antiarrhythmic and beta-blocker APIs.
| Chemical Name | N-[4-(2-Chloroacetyl)phenyl]methanesulfonamide |
| Molecular Formula | C9H10ClNO3S |
| Molecular Weight | 247.7 |
| CAS Number | 64488-52-4 |