BOP reagent

BOP reagent

Names
IUPAC name ((1H-Benzo[d][1,2,3]triazol-1-yl)oxy)tris(dimethylamino)phosphonium hexafluorophosphate(V)
Other names Castro's reagent
Identifiers
CAS Number	56602-33-6^Y
3D model (JSmol)	Interactive image
ChemSpider	133386^Y
ECHA InfoCard	100.054.782
PubChem CID	151348
UNII	LBD3UE345W^Y
CompTox Dashboard (EPA)	DTXSID60205170
InChI InChI=1S/C12H22N6OP.F6P/c1-15(2)20(16(3)4,17(5)6)19-18-12-10-8-7-9-11(12)13-14-18;1-7(2,3,4,5)6/h7-10H,1-6H3;/q+1;-1^Y Key: MGEVGECQZUIPSV-UHFFFAOYSA-N^Y
SMILES F[P-](F)(F)(F)(F)F.n1nn(O[P+](N(C)C)(N(C)C)N(C)C)c2ccccc12
Properties
Chemical formula	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)
Solubility in water	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). Y verify (what is ^YN ?) Infobox references

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.

See also

• PyBOP, a related phosphonium reagent for amide bond formation
• PyAOP, a related phosphonium reagent for amide bond formation

References

1. "(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 226084". BOP Reagent. Retrieved 2020-02-11.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.