BOP reagent
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| Template:Longitem | C12H22F6N6OP2 |
| Molar mass | 442.287 g/mol |
| Appearance | White crystalline powder |
| Melting point | Template:Chembox CalcTemperatures |
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Script error: No such module "Unsubst". BOP (benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) is a reagent commonly used for the synthesis of amides from carboxylic acids and amines in peptide synthesis.[1][2] It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions.[3] This reagent has advantages in peptide synthesis since it avoids side reactions like the dehydration of asparagine or glutamine residues.[4] BOP has used for the synthesis of esters from the carboxylic acids and alcohols.[5] BOP has also been used in the reduction of carboxylic acids to primary alcohols with sodium borohydride (NaBH4).[6] Its use raises safety concerns since the carcinogenic compound HMPA is produced as a stoichiometric by-product.
See also
- PyBOP, a related phosphonium reagent for amide bond formation
- PyAOP, a related phosphonium reagent for amide bond formation