PyBOP Chemical Properties

Melting point:

154-156 °C (dec.)(lit.)

Density 

1.438 at 20℃

vapor pressure 

0-0Pa at 20-50℃

storage temp. 

2-8°C

solubility 

methanol: 25 mg/mL, clear

form 

Fine Crystalline Powder

color 

White to off-white

Sensitive 

Moisture Sensitive

BRN 

3584612

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

InChIKey

BYCLGHOAELJLOF-UHFFFAOYSA-M

SMILES

[P+](ON1N=NC2C=CC=CC1=2)(N1CCCC1)(N1CCCC1)N1CCCC1.[P-](F)(F)(F)(F)(F)F

LogP

-0.3 at 26℃ and pH3.5-3.7

CAS DataBase Reference

128625-52-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-44-36/37/38

Safety Statements 

26-36-24/25-37/39

RIDADR 

UN 1325 4.1/PG 2

WGK Germany 

3

F 

8-10-21

Hazard Note 

Irritant

HS Code 

29339980

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

PyBOP Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

One of the most convenient coupling reagents for peptide synthesis without carcinogenic by-products. It replaces BOP reagent. This is especially suitable for solid-phase peptide synthesis, avoids racemization.

Uses

1H-Benzotriazol-1-yloxytri(1-pyrrolidinyl) phosphonium hexafluorophosphate (PyBOP) is a peptide coupling reagent utilized in solid phase peptide synthesis. It is also used as a substitute for the (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) reagent.

Uses

PyBOP is a reagent for: Synthesis of single labeled oligonucleotides that fluoresce upon matched hybridization
Generation of endocrine disruptor chemical binders
Cycloaddition to template-assembled multivalent peptide conjugates

Definition

PyBOP (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate) coupling reagent was selected for the peptidic bond formation. This selection was because PyBOP is efficient and could generate less toxic byproducts. PyBOP is an efficient coupling reagent utilized in solid-phase peptide synthesis. It reacts similarly to BOP, but its byproduct is not highly carcinogenic. PyBOP was utilized in the solid-phase synthesis of the tetrapeptide H-Ile-Ala-Leu-Pro-OH on 2-chlorotrityl resin. In contrast to uronium-based coupling reagents, PyBOP does not form guanidinated byproducts when used in excess. This makes it useful in fragment condensation reactions and head-to-tail cyclizations[1].

General Description

(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) is an activator of carboxyl group commonly used in peptide synthesis. It also participates in the carboxylic acid esterification. It shows characteristics similar to benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and can be utilized as an alternative to BOP in peptide bond formation.

References

[1] Maharani, R. et al. “Good coupling performance of PyBOP in the solid-phase synthesis of tetrapeptide, OH-Pro-Leu-Ala-Ileu-NH2.” 2017. 0.

PyBOP(128625-52-5)Related Product Information

• Bis(2-oxo-3-oxazolidinyl)phosphinic chloride
• DEPBT
• TSTU
• 5-Chloro-1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide hexafluorophosphate
• Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate
• Diphenylphosphoryl azide
• 1H-Benzotriazole
• Hexafluorophosphoric acid
• Potassium hexafluorophosphate
• Lithium hexafluorophosphate
• Sodium hexafluorophosphate
• Hexafluorophosphate
• TRIS(DIETHYLAMINO)PHOSPHINE
• 1-Hydroxybenzotriazole hydrate
• 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate
• Hexamethylphosphorous triamide
• Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate