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PyBOP

From Wikipedia, the free encyclopedia
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 InfoCard100.125.168Edit 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 mass520.401 g·mol−1
AppearanceWhite crystals
Melting point150 °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 theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepareamides fromcarboxylic acids andamines in the context ofpeptide synthesis.[3] It can be prepared from1-hydroxybenzotriazole and achlorophosphonium reagent under basic conditions.[4] It is a substitute for theBOP reagent that avoids the formation of thecarcinogenic waste productHMPA.[5] Thermal hazard analysis bydifferential scanning calorimetry (DSC) shows PyBOP is potentially explosive.[6]

See also

[edit]

References

[edit]
  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 (8):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.
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