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8.51004

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:
56602-33-6
Molecular Weight:
442.28
UNSPSC Code:
12352107
EC Index Number:
260-279-1
NACRES:
NA.22
MDL number:
MFCD00011948
Assay:
≥99.0% (HPLC)
Form:
powder
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Quality Segment

200

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

SMILES string

F[P-](F)(F)(F)(F)F.[P](=[N+](C)C)(N(C)C)(N(C)C)O[n]1nnc2c1cccc2

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.

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

Other Notes

Replaces: 01-62-0001

Legal Information

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

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

EUH044

Storage Class

4.1A - Other explosive hazardous materials

wgk

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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