8.51004

BOP

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

• Sinônimo(s): BOP, Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphoniumhexafluorophosphate, Castro′s Reagent
• Fórmula empírica (Notação de Hill): C₁₂H₂₂N₆OP · F₆P
• Número CAS: 56602-33-6
• Peso molecular: 442.28
• Número MDL: MFCD00011948
• Código UNSPSC: 12352107
• Número do índice EC: 260-279-1
• NACRES: NA.22

Propriedades

• Nível de qualidade: 200
• linha de produto: Novabiochem^®
• Ensaio: ≥99.0% (HPLC)
• Formulário: powder
• adequação da reação: reaction type: Coupling Reactions
• fabricante/nome comercial: Novabiochem^®
• pf: 138-145 °C
• aplicação(ões): peptide synthesis
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres SMILES: 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
• chave InChI: MGEVGECQZUIPSV-UHFFFAOYSA-N

Descrição

Descrição geral

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.

Ligação

Replaces: 01-62-0001

Nota de análise

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

Informações legais

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

Informações de segurança

• Pictogramas: GHS02,GHS07
• Palavra indicadora: Danger
• Frases de perigo: H228 - H315 - H335
• Declarações de precaução: P210 - P240 - P241 - P261 - P264 - P302 + P352
• Classificações de perigo: Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3
• Órgãos-alvo: Respiratory system
• Perigos de suplementos: EUH044
• Código de classe de armazenamento: 4.1A - Other explosive hazardous materials
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable