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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%

Numéro CAS
68641-49-6
Synonymes
BOP-Cl

Dimensions Prix ($) Quantité Disponibilité
1g 14,72
5g 46,71
25g 156,19
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Bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 97%

MDL
MFCD00010077

Propriétés chimiques

Formule
C6H8ClN2O5P
Poids formulaire
254.57
Point de fusion
ca 195° dec.
Sensibilité
Moisture Sensitive
Solubilité
Hydrolyzes with water.

Applications

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.

Notes

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.

Références bibliographiques

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).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H314-H318

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

Mentions de prudence: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. 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. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
3654596
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2934.99
TSCA
No
RTECS
SZ5871000

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