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68641-49-6 - Bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 97% - BOP-Cl - L08775 - Alfa Aesar

L08775 Bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 97%

CAS-Nummer
68641-49-6
Synonyme
BOP-Cl

Größe Preis ($) Menge Verfügbarkeit
1g 17,80
5g 47,90
25g 162,00
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Bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 97%

MDL
MFCD00010077

Chemische Eigenschaften

Formel
C6H8ClN2O5P
Molmasse
254.57
Schmelzpunkt
ca 195° dec.
Sensitivität
Moisture Sensitive
Löslichkeit
Hydrolyzes with water.

Anwendungen

Bis(2-oxo-3-oxazolidinyl)phosphinic chloride was used in the preparation of hexadepsipeptide. Also used as reagent is used for activating the carboxylic group, synthesis of amides, esters and peptides.

Bemerkungen

Moisture Sensitive, store away from moisture. Store in cool. Keep container tightly closed in a dry and well-ventilated place. Store away from oxidizing agent.

Literaturverweise

T Miyazawa; T Donkai; T Yamada; S Kuwata. Effect of copper(II) chloride on suppression of racemization in peptide synthesis by the mixed anhydride and related methods. International Journal of Peptide and Protein Reseach. 1992, 40 (1), 49-53.

H T Le; J F Gallard; M Mayer; E Guittet; R Michelot. Use of BOP-Cl in the presence of Boc-amino monothioacids for the thioacylation of imino acid residues. Bioorganic & Medicinal Chemistry. 1996, 4(12), 2201-2209.

Coupling reagent for which the rates of reaction with various nucleophiles are sufficiently different to permit a genuine "one-step" coupling of carboxylic acids with amines: Synthesis, 547 (1980). Particularly suitable for coupling N-alkyl amino acids: J. Org. Chem., 51, 3350 (1986). For discussion of strategies for one-step coupling in synthesis of amides, see: Synthesis, 413 (1984), and of the scope and limitations of the reagent in peptide coupling, see: Int. J. Pept. Prot. Res., 29, 574 (1987); J. Org. Chem., 55, 2895 (1990). See also Appendix 6.

For use in the direct selective 5'-acylation of nucleosides by carboxylic acids, (without 3'-protection), see: Tetrahedron, 44, 229 (1988). For high yield dehydration of carboxylic acids to anhydrides, see: Synthesis, 616 (1981). Also used in macrolide cyclization: J. Am. Chem. Soc., 104, 6818 (1982), and in formation of acyclic esters: Synth. Commun., 14, 515 (1984).

The mixed anhydride formed with carboxylic acids adds to imines to give ß-lactams: Synthesis, 63 (1982):

These are also formed in high yield by cyclization of ß-amino acids: Bull. Korean Chem. Soc., 12, 457 (1991).

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Sicherheitshinweise: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
3654596
Gefahrenklasse
8
Verpackungsgruppe
II
Harmonized Tariff Code
2934.99
TSCA
No
RTECS
SZ5871000

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