BOP reagent
| Names | |
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| IUPAC name
((1H-Benzo[d][1,2,3]triazol-1-yl)oxy)tris(dimethylamino)phosphonium hexafluorophosphate(V)
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| Other names
Castro's reagent
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C12H22F6N6OP2 | |
| Molar mass | 442.287 g/mol |
| Appearance | White crystalline powder |
| Melting point | 136 to 140 °C (277 to 284 °F; 409 to 413 K) |
| Partially soluble in cold water reacts (decomposes) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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This article may be too technical for most readers to understand. (January 2021) |
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
[edit | edit source]- PyBOP, a related phosphonium reagent for amide bond formation
- PyAOP, a related phosphonium reagent for amide bond formation
References
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