PyBOP

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]

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
UNII	Y6KQR4GY6T Y
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
Occupational safety and health (OHS/OSH):
Main hazards	Irritant
GHS labelling:[1][2][citation needed]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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 YN ?) Infobox references

See also

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