The Hofmann rearrangement (also known as the Hofmann degradation) is the reaction of a primary amide with a halogen (bromine or chlorine) in the presence of a base (sodium or potassium hydroxide) to produce a primary amine. The reaction transforms a primary amide to a primary amine, losing one carbon in the process.
| Starting Material | Intermediate | Product | CAS No. | Application |
|---|---|---|---|---|
| Phthalic Anhydride (85-44-9) ↓ Phthalimide (85-41-6) ↓ Isatoic Anhydride (118-48-9) |
— | Methyl Anthranilate | 134-20-3 | Fragrance, Pharma |
| — | Ethyl Anthranilate | 87-25-2 | Fragrance, Cosmetics & Food Flavorings | |
| — | Decyl Anthranilate | 18189-07-6 | Fragrance & Cosmetic | |
| — | N-Butyl Anthranilate | 7756-96-9 | Fragrance & Flavor | |
| — | Phenyl Ethyl Anthranilate | 133-18-6 | Flavor | |
| — | N-Methyl Isatoic Anhydride | 10328-92-4 | Intermediate for API, Dyes | |
| — | Anthranilamide | 88-68-6 | PET bottles as acetaldehyde scavenger, Dyes & Pharma | |
| — | 5-Chloro Methyl Anthranilate | 5202-89-1 | Tolvaptan | |
| — | 2-Amino-5-Chloro Benzoic Acid | 635-21-2 | Pharma, Agro | |
| Side Products | 2-[(2-Aminobenzoyl) Amino] Benzoic Acid | 612-34-0 | Pigments | |
| Side Products | 2-[(2-Hydroxybenzoyl) Amino] Benzoic Acid | 13316-98-8 | Pharma | |
| Fragrance Product | Dimethyl Anthranilate | 85-91-6 | Fragrance | |