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8.51004

Sigma-Aldrich

BOP

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H22N6OP · F6P
CAS Number:
Molecular Weight:
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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

Storage Class Code

4.1A - Other explosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Articles

Novabiochem® coupling reagents for in situ activation are fast-reacting and compatible with various amino acids.

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