Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

• Catalog No.: L08775
• CAS Number: 68641-49-6
• M. F.: C6H8ClN2O5P
• M. W.: 254.564881
• Purity: 97%

SYNONYMS

• Title: 双(2-氧代'-3-噁唑烷基)次磷酰氯
• IUPAC name: bis(2-oxo-1,3-oxazolidin-3-yl)phosphinoyl chloride
• IUPAC Traditional name: bis(2-oxo-1,3-oxazolidin-3-yl)phosphinoyl chloride
• Synonyms: BOP-Cl

DATABASE IDS

• Beilstein Number: 3654596
• MDL Number: MFCD00010077
• CAS Number: 68641-49-6

PROPERTIES

• Purity: 97%
• Melting Point: ca 195°C dec.
• GHS Hazard statements: H314-H318
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Risk Statements: 34
• RTECS: SZ5871000
• Safety Statements: 26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: II

REFERENCES

• 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 ?-lactams: Synthesis, 63 (1982):
  
• These are also formed in high yield by cyclization of ?-amino acids: Bull. Korean Chem. Soc., 12, 457 (1991).