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Key Documents

8.51004

Sigma-Aldrich

BOP

Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate Novabiochem®

Sinónimos:

BOP, Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphoniumhexafluorophosphate, Castro′s Reagent

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About This Item

Fórmula empírica (notación de Hill):
C12H22N6OP · F6P
Número de CAS:
Peso molecular:
442.28
MDL number:
UNSPSC Code:
12352107
EC Index Number:
260-279-1
NACRES:
NA.22

Quality Level

product line

Novabiochem®

assay

≥99.0% (HPLC)

form

powder

reaction suitability

reaction type: Coupling Reactions

manufacturer/tradename

Novabiochem®

mp

138-145 °C

application(s)

peptide synthesis

storage temp.

2-8°C

InChI

1S/C12H22N6OP.F6P/c1-15(2)20(16(3)4,17(5)6)19-18-12-10-8-7-9-11(12)13-14-18;1-7(2,3,4,5)6/h7-10H,1-6H3;/q+1;-1

InChI key

MGEVGECQZUIPSV-UHFFFAOYSA-N

General description

Peptide coupling reagent which suppresses enantiomerization [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15]. Reduction of carboxylic acids activated with BOP provides a facile route to alcohols [16]. Novabiochem® recommends the replacement of BOP by PyBOP (for PyBOP please see 851009). The manufacture of BOP, as well as its utilization, involves the use or the formation of hexamethylphosphotriamide, the carcinogenicity and respiratory toxicity of which has been the subject of numerous reports.

Associated Protocols and Technical Articles

Guide to Selection of Coupling Reagents Literature references

[1] B. Castro, et al. (1975) Tetrahedron Lett., 16, 1219.
[2] B. Castro, et al. (1976) Synthesis, 751.
[3] B. Castro, et al. (1977) Synthesis, 413.
[4] B. Castro, et al. (1977) J. Chem. Res. (S), 182.
[5] P. Rivaille, et al. (1980) Tetrahedron, 36, 3413.
[6] D. L. Nguyen, et al. (1985) J. Chem. Soc., Perkin Trans. 1, 1025.
[7] D. L. Nguyen, et al. (1987) J. Chem. Soc., Perkin Trans. 1, 1915.
[8] A. Fournier, et al. (1988) Int. J. Peptide Protein Res., 31, 86 and 231.
[9] J.-P. Briand, et al. (1989) Pept. Res., 2, 381.
[10] A. Fournier, et al. (1989) Int. J. Peptide Protein Res., 33, 133.
[11] D. L. Nguyen, et al. (1989) Biochem. Biophys. Res. Commun., 162, 1425.
[12] W. K. Rule, et al. in ′Peptides 1988, Proc. 20th European Peptide Symposium′, G. Jung & E. Bayer (Eds), Walter de Gruyter, Berlin, 1989, pp. 238.
[13] M. Forest, et al. (1990) Int. J. Peptide Protein Res., 35, 89.
[14] R. Seyer, et al. (1990) Int. J. Peptide Protein Res., 35, 465.
[15] H. Gausepohl, et al. in ′Innovation & Perspectives in Solid Phase Synthesis, 2nd International Symposium′, R. Epton (Eds), Intercept UK Ltd., Andover, 1993, pp. 387.
[16] R. P. McGeary (1998) Tetrahedron Lett., 39, 3319.

Linkage

Replaces: 01-62-0001

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (0.6 mmole in 1 ml DMF): clearly soluble

Legal Information

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

pictograms

FlameExclamation mark

signalword

Danger

Hazard Classifications

Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

supp_hazards

Storage Class

4.1A - Other explosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Artículos

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.

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