Structure via PubChem · Public domain (PubChem)
PyBOP
Sign in to saveAlso known as benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate
PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis. It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions. It is a substitute for the BOP reagent that avoids the formation of the carcinogenic waste product HMPA. Thermal hazard analysis by differential scanning calorimetry (DSC) shows PyBOP is potentially explosive.
Chemical data
- Formula
- C18H28F6N6OP2
- Molecular weight
- 520.4 g/mol
- IUPAC name
- benzotriazol-1-yloxy(tripyrrolidin-1-yl)phosphanium hexafluorophosphate
- SMILES
- C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
- InChIKey
- VIAFLMPQBHAMLI-UHFFFAOYSA-N
- Polar surface area
- 49.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 520.170402
Show 3 more facts
- canonical SMILES
- C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F
- chemical formula
- C₁₈H₂₈F₆N₆OP₂
- Commons category
- PyBOP
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis. It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions. It is a substitute for the BOP reagent that avoids the formation of the carcinogenic waste product HMPA. Thermal hazard analysis by differential scanning calorimetry (DSC) shows PyBOP is potentially explosive.
==See also== BOP reagent DEPBT, a related reagent that contains no phosphorus-nitrogen bonds HATU HBTU
Excerpted from Wikipedia’s “PyBOP” article, available under the CC BY-SA 4.0 licence.
Available in 10 languages
via Wikidata sitelinks · CC0