PyBOP

PyBOP (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate) is a peptide coupling reagent used in solid phase peptide synthesis. It is used as a substitute for the BOP reagent - avoiding the formation of the carcinogenic waste product HMPA.[1]

PyBOP

Names
IUPAC name (Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate
Other names PyBOP
Identifiers
CAS Number	128625-52-5^N
3D model (JSmol)	Interactive image
ChemSpider	2006820^Y
ECHA InfoCard	100.125.168
PubChem CID	2724699
CompTox Dashboard (EPA)	DTXSID40369209
InChI InChI=1S/C18H28N6OP.F6P/c1-2-10-18-17(9-1)19-20-24(18)25-26(21-11-3-4-12-21,22-13-5-6-14-22)23-15-7-8-16-23;1-7(2,3,4,5)6/h1-2,9-10H,3-8,11-16H2;/q+1;-1^Y Key: VIAFLMPQBHAMLI-UHFFFAOYSA-N^Y InChI=1/C18H28N6OP.F6P/c1-2-10-18-17(9-1)19-20-24(18)25-26(21-11-3-4-12-21,22-13-5-6-14-22)23-15-7-8-16-23;1-7(2,3,4,5)6/h1-2,9-10H,3-8,11-16H2;/q+1;-1 Key: VIAFLMPQBHAMLI-UHFFFAOYAY
SMILES F[P-](F)(F)(F)(F)F.n4nn(O[P+](N1CCCC1)(N2CCCC2)N3CCCC3)c5ccccc45
Properties
Chemical formula	C18H28F6N6OP2
Molar mass	520.401 g·mol^−1
Appearance	White crystals
Melting point	150 °C (302 °F; 423 K)
Hazards
Main hazards	Irritant
R-phrases (outdated)	R36/37/38
S-phrases (outdated)	S26-S36
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

See also

• BOP reagent
• DEPBT, a related reagent that contains no phosphorus-nitrogen bonds
• HATU
• HBTU

References

1. Coste, J.; Le-Nguyen, D.; Castro, B. (1990). "PyBOP®: A new peptide coupling reagent devoid of toxic by-product". Tetrahedron Letters. 31 (2): 205. doi:10.1016/S0040-4039(00)94371-5.