PyBOP

PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium 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.[3]

PyBOP
Ball-and-stick model of the component ions of PyBOP
Names
IUPAC name
(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate
Other names
PyBOP
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.125.168
UNII
  • 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 checkY
    Key: VIAFLMPQBHAMLI-UHFFFAOYSA-N checkY
  • 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
  • F[P-](F)(F)(F)(F)F.n4nn(O[P+](N1CCCC1)(N2CCCC2)N3CCCC3)c5ccccc45
Properties
C18H28F6N6OP2
Molar mass 520.401 g·mol−1
Appearance White crystals
Melting point 150 °C (302 °F; 423 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
GHS labelling:[1][2]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P305+P351+P338
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

See also

References
  1. Sigma-Aldrich Co., product no. {{{id}}}.
  2. GHS: Sigma-Aldrich377848
  3. 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.


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