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8.51009

Sigma-Aldrich

PyBOP®

greener alternative

Novabiochem®

Synonym(s):

Benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate, PyBOP®

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About This Item

Empirical Formula (Hill Notation):
C18H28N6OP · F6P
CAS Number:
128625-52-5
Molecular Weight:
520.39
MDL number:
MFCD00077411
UNSPSC Code:
12352107
NACRES:
NA.22

Quality Level

400

product line

Novabiochem®

assay

≥99.0% (HPLC)

form

powder

reaction suitability

reaction type: Coupling Reactions

manufacturer/tradename

Novabiochem®

greener alternative product characteristics

Less Hazardous Chemical Syntheses
Learn more about the Principles of Green Chemistry.

mp

140-155 °C

application(s)

peptide synthesis

greener alternative category

Aligned

storage temp.

2-8°C

InChI

1S/C18H28N6OP/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/h1-2,9-10H,3-8,11-16H2/q+1

InChI key

WGNZRLMOMHJUSP-UHFFFAOYSA-N

Related Categories

General description

The standard in situ coupling reagent for solid phase peptide synthesis [1,2,3,4,5]. This product can replace BOP in all applications without loss of performance. Unlike uronium-based reagents, PyBOP® does not give rise to guanidinated by-products during cyclization and fragment condensation reactions.

Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents

Literature references

[1] J. Martinez, et al. (1985) J. Med. Chem., 28, 1874.
[2] J. Coste, et al. (1990) Tetrahedron Lett., 31, 205.
[3] G. B. Fields, et al. in ′Innovation & Perspectives in Solid Phase Synthesis, 1st International Symposium′, R. Epton (Eds), SPCC UK Ltd., Birmingham, 1990, pp. 241.
[4] T. Høeg-Jensen, et al. (1991) Tetrahedron Lett., 32, 7617.
[5] R. von Eggelkraut-Gottanka, et al. (2003) Tetrahedron Lett., 44, 3551.
We are committed to bringing you greener alternative products, which adhere to one or more of the 12 Principles of Green Chemistry. PyBOP is widely used as a substitute for the BOP, with the aim of avoiding formation of hexamethylphosphoric triamide (HMPA) which is a carcinogenic side product. Click here for more information.

Linkage

Replaces: 01-62-0016

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany
PyBOP is a registered trademark of Merck KGaA, Darmstadt, Germany

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pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Sens. 1

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Articles

Peptide Coupling Reagents Selection Guide

Novabiochem® offers a large number of coupling reagents for in situ activation. In situ activating reagents are easy to use, fast reacting – even with sterically hindered amino acids, and their use is generally free of side reactions.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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