PyBOP

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 Edit this at Wikidata
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][citation needed]
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).
☒N verify (what is checkY☒N ?)

PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis.[3] It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions.[4] It is a substitute for the BOP reagent that avoids the formation of the carcinogenic waste product HMPA.[5] Thermal hazard analysis by differential scanning calorimetry (DSC) shows PyBOP is potentially explosive.[6]

  1. ^ Sigma-Aldrich Co., product no. {{{id}}}.
  2. ^ GHS: Sigma-Aldrich377848
  3. ^ 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.
  4. ^ Hoffmann, Frank; Jäger, Lothar; Griehl, Carola (2003). "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.
  5. ^ 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.
  6. ^ Sperry, Jeffrey B.; Minteer, Christopher J.; Tao, JingYa; Johnson, Rebecca; Duzguner, Remzi; Hawksworth, Michael; Oke, Samantha; Richardson, Paul F.; Barnhart, Richard; Bill, David R.; Giusto, Robert A.; Weaver, John D. (2018-09-21). "Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing". Organic Process Research & Development. 22 (9): 1262–1275. doi:10.1021/acs.oprd.8b00193. ISSN 1083-6160.