| |
| Names | |
|---|---|
|
IUPAC name
((1H-Benzo[d][1,2,3]triazol-1-yl)oxy)tris(dimethylamino)phosphonium hexafluorophosphate(V)
| |
| Other names
Castro's reagent
| |
| Identifiers | |
3D model (
JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.054.782 |
PubChem
CID
|
|
| UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
| 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).
| |
 | 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 redisues. [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.
- PyBOP, a related phosphonium reagent for amide bond formation
- PyAOP, a related phosphonium reagent for amide bond formation
- ^ "(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 226084". BOP Reagent. Retrieved 2020-02-11.
- ^ Mansour, Tarek S.; Bardhan, Sujata; Wan, Zhao-Kui (2010). "Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications". Synlett. 2010 (08): 1143–1169. doi: 10.1055/s-0029-1219820. ISSN 0936-5214.
- ^ Hoffmann, Frank; Jäger, Lothar; Griehl, Carola (2003-02-01). "Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation". Phosphorus, Sulfur, and Silicon and the Related Elements. 178 (2): 299–309. doi: 10.1080/10426500307942. ISSN 1042-6507.
- ^ Prasad, KVSRG; Bharathi, K; Haseena, Banu B (2011). "Applications of Peptide Coupling Reagents- An Update" (PDF). International Journal of Pharmaceutical Sciences Review and Research. 8 (1): 108–119.
- ^ Kim, Moon H.; Patel, Dinesh V. (1994-08-01). ""BOP" as a reagent for mild and efficient preparation of esters". Tetrahedron Letters. 35 (31): 5603–5606. doi: 10.1016/S0040-4039(00)77257-1. ISSN 0040-4039.
- ^ McGeary, Ross P. (1998). "Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride". Tetrahedron Letters. 39 (20): 3319–3322. doi: 10.1016/S0040-4039(98)00480-8. ISSN 0040-4039.
 | This article about an organic compound is a stub. You can help Wikipedia by expanding it. |
|
| |
| Names | |
|---|---|
|
IUPAC name
((1H-Benzo[d][1,2,3]triazol-1-yl)oxy)tris(dimethylamino)phosphonium hexafluorophosphate(V)
| |
| Other names
Castro's reagent
| |
| Identifiers | |
3D model (
JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.054.782 |
PubChem
CID
|
|
| UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
| 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).
| |
| 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 redisues. [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.
- PyBOP, a related phosphonium reagent for amide bond formation
- PyAOP, a related phosphonium reagent for amide bond formation
- ^ "(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 226084". BOP Reagent. Retrieved 2020-02-11.
- ^ Mansour, Tarek S.; Bardhan, Sujata; Wan, Zhao-Kui (2010). "Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications". Synlett. 2010 (08): 1143–1169. doi: 10.1055/s-0029-1219820. ISSN 0936-5214.
- ^ Hoffmann, Frank; Jäger, Lothar; Griehl, Carola (2003-02-01). "Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation". Phosphorus, Sulfur, and Silicon and the Related Elements. 178 (2): 299–309. doi: 10.1080/10426500307942. ISSN 1042-6507.
- ^ Prasad, KVSRG; Bharathi, K; Haseena, Banu B (2011). "Applications of Peptide Coupling Reagents- An Update" (PDF). International Journal of Pharmaceutical Sciences Review and Research. 8 (1): 108–119.
- ^ Kim, Moon H.; Patel, Dinesh V. (1994-08-01). ""BOP" as a reagent for mild and efficient preparation of esters". Tetrahedron Letters. 35 (31): 5603–5606. doi: 10.1016/S0040-4039(00)77257-1. ISSN 0040-4039.
- ^ McGeary, Ross P. (1998). "Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride". Tetrahedron Letters. 39 (20): 3319–3322. doi: 10.1016/S0040-4039(98)00480-8. ISSN 0040-4039.
|
| This article about an organic compound is a stub. You can help Wikipedia by expanding it. |