BOP reagent

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.

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

See also

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