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 ;
3D model (JSmol)	Interactive image;
ChemSpider	133386 ;
PubChem CID	151348;
UNII	LBD3UE345W ;
	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 Key: MGEVGECQZUIPSV-UHFFFAOYSA-N ;
	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).
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	Infobox references

BOP (benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) reagent is a reagent commonly used in the synthesis of peptides. Its use is discouraged because coupling using BOP liberates HMPA which is carcinogenic, although for small scale use in an organic laboratory this is not a great disadvantage as it is in large scale industrial usage. BOP has been used for peptide coupling, synthesis of esters, esterification of carboxylic acids, or as a catalyst.^[1]^[2] This reagent is advantageous in peptide coupling to other derived reagents because there are no side reactions from the dehydration of asparagine or glutamine.^[2] In peptide coupling the BOP reagent works well because it forms reactive intermediates which allow for the amines to bond together with little energy loss.^[3] In the reduction of carboxylic acids, using the BOP reagent with NaBH₄ resulted in high percent yields.^[3]

References

↑ "(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 226084". https://www.sigmaaldrich.com/catalog/product/aldrich/226084.
↑ ^2.0 ^2.1 Prasad, KVSRG; Bharathi, K; Haseena, Banu B (5 January 2011). "Applications of Peptide Coupling Reagents- An Update". International Journal of Pharmaceutical Sciences Review and Research 8 (1): 108–119.
↑ ^3.0 ^3.1 McGeary, Ross P. (1998-05-14). "Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride" (in en). Tetrahedron Letters 39 (20): 3319–3322. doi:10.1016/S0040-4039(98)00480-8. ISSN 0040-4039.

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[1] "(Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 226084". https://www.sigmaaldrich.com/catalog/product/aldrich/226084.

[:0-2] 2.0 ^2.1 Prasad, KVSRG; Bharathi, K; Haseena, Banu B (5 January 2011). "Applications of Peptide Coupling Reagents- An Update". International Journal of Pharmaceutical Sciences Review and Research 8 (1): 108–119.

[:1-3] 3.0 ^3.1 McGeary, Ross P. (1998-05-14). "Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride" (in en). Tetrahedron Letters 39 (20): 3319–3322. doi:10.1016/S0040-4039(98)00480-8. ISSN 0040-4039.

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BOP reagent

Topic: Chemistry

See also

References