8.51004

BOP

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

• Synonyme(s) : BOP, Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphoniumhexafluorophosphate, Castro′s Reagent
• Formule empirique (notation de Hill): C₁₂H₂₂N₆OP · F₆P
• Numéro CAS: 56602-33-6
• Poids moléculaire : 442.28
• Numéro MDL: MFCD00011948
• Code UNSPSC : 12352107
• Numéro de classement CE : 260-279-1
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 200
• Gamme de produits: Novabiochem^®
• Pureté: ≥99.0% (HPLC)
• Forme: powder
• Capacité de réaction: reaction type: Coupling Reactions
• Fabricant/nom de marque: Novabiochem^®
• Pf: 138-145 °C
• Application(s): peptide synthesis
• Température de stockage: 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
• Clé InChI: MGEVGECQZUIPSV-UHFFFAOYSA-N

Description

Description générale

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.

Liaison

Replaces: 01-62-0001

Remarque sur l'analyse

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

Informations légales

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

Informations sur la sécurité

• Pictogrammes: GHS02,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H228 - H315 - H335
• Conseils de prudence: P210 - P240 - P241 - P261 - P264 - P302 + P352
• Classification des risques: Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3
• Organes cibles: Respiratory system
• Risques supp: EUH044
• Code de la classe de stockage: 4.1A - Other explosive hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable