8.51004

BOP

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

• Sinonimo/i: BOP, Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphoniumhexafluorophosphate, Castro′s Reagent
• Formula empirica (notazione di Hill): C₁₂H₂₂N₆OP · F₆P
• Numero CAS: 56602-33-6
• Peso molecolare: 442.28
• Numero MDL: MFCD00011948
• Codice UNSPSC: 12352107
• Numero indice EU: 260-279-1
• NACRES: NA.22

Proprietà

• Livello qualitativo: 200
• Nome Commerciale: Novabiochem^®
• Saggio: ≥99.0% (HPLC)
• Forma fisica: powder
• Impiego in reazioni chimiche: reaction type: Coupling Reactions
• Produttore/marchio commerciale: Novabiochem^®
• Punto di fusione: 138-145 °C
• applicazioni: peptide synthesis
• Temperatura di conservazione: 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; MGEVGECQZUIPSV-UHFFFAOYSA-N

Descrizione

Descrizione generale

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

Risultati analitici

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

Note legali

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

Informazioni sulla sicurezza

• Pittogrammi: GHS02,GHS07
• Avvertenze: Danger
• Indicazioni di pericolo: H228 - H315 - H335
• Consigli di prudenza: P210 - P240 - P241 - P261 - P264 - P302 + P352
• Classi di pericolo: Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3
• Organi bersaglio: Respiratory system
• Rischi supp: EUH044
• Codice della classe di stoccaggio: 4.1A - Other explosive hazardous materials
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable