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
• 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

Properties

• 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

Description

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

Safety Information

• pictograms: GHS02,GHS07
• signalword: Danger
• pcodes: P210 - P240 - P241 - P261 - P264 - P302 + P352
• 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
• hcodes: H228,H315,H335