8.51010

PyBroP

Novabiochem^®

• Synonym(s): PyBroP, Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate
• Empirical Formula (Hill Notation): C₁₂H₂₄BrN₃P · F₆P
• CAS Number: 132705-51-2
• Molecular Weight: 466.18
• MDL number: MFCD00077412
• UNSPSC Code: 12352107
• NACRES: NA.22

Properties

• Quality Level: 200
• product line: Novabiochem^®
• assay: ≥98.0% (HPLC)
• form: powder
• reaction suitability: reaction type: Coupling Reactions
• manufacturer/tradename: Novabiochem^®
• mp: >100 °C
• application(s): peptide synthesis
• storage temp.: 2-8°C
• InChI: 1S/C12H24BrN3P.F6P/c13-17(14-7-1-2-8-14,15-9-3-4-10-15)16-11-5-6-12-16;1-7(2,3,4,5)6/h1-12H2;/q+1;-1
• InChI key: CYKRMWNZYOIJCH-UHFFFAOYSA-N

Description

General description

A superior reagent for rapid and effective coupling of N-methyl amino acids with low enantiomerization and for other critical applications ^{[1,2,3,4,5,6,7,8]}. The coupling of N-methyl amino acids is difficult, and usually only gives low to moderate yields of products which are often contaminated with unwanted diastereomers. Many coupling reagents are ineffective or not practical to use: BOP and HOBt are often useless; BOP-Cl, pivaloyl chloride and Dpp-Cl require long reaction times and preactivation at 0°C.For coupling γ-aminoisobutyric acid (Aib), PyBrOP^® is most effective when used with dimethylaminopyridine (DMAP) ^[3].

Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents


Literature references

^[1] J. Coste, et al. in ′Peptides, Chemistry, Structure & Biology, Proc. 11th American Peptide Symposium′, J. E. Rivier & G. R. Marshall (Eds), ESCOM, Leiden, 1990, pp. 900.
^[2] J. Coste, et al. (1990) Tetrahedron Lett., 31, 669.
^[3] J. Coste, et al. in ′Peptides 1990, Proc. 21st European Peptide Symposium′, E. Giralt & D. Andreu (Eds), ESCOM, Leiden, 1990, pp. 76.
^[4] J. Coste, et al. (1991) Tetrahedron Lett., 32, 1967.
[5] P. W. Baures, et al. (1997) J. Peptide Res., 50, 1.
^[6] T. Doi, et al. (1999) Synlett, 11, 1751.
^[7] A. M. Boldi, et al. (2001) J. Comb. Chem., 3, 367.
^[8] S. Gazal, et al. (2001) J. Peptide Res., 58, 527.

Linkage

Replaces: 01-62-0017

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 98.0 % (a/a)

Legal Information

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

PyBroP is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H314
• pcodes: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• Storage Class: 8A - Combustible, corrosive hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable