Substance
ID:735775
Names and Identifiers
IUPAC Traditional name
bis(2-oxo-1,3-oxazolidin-3-yl)phosphinoyl chloride
Synonyms
Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideBOP-Cl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
Properties
Physical Property
Melting Point
ca 195°C dec.
Safety Information
GHS Hazard statements
H314-H318
RTECS
SZ5871000
GHS Pictograms
Corrosive to metals, category 1
Skin corrosion, categories 1A,1B,1C
Serious eye damage, category 1
Safety Statements
26-36/37/39-45
European Hazard Symbols
Corrosive (C)Hazard Class
8
Risk Statements
34
Storage Warning
Moisture Sensitive
UN Number
UN3261
Packing Group
II
TSCA Listed
否
GHS Precautionary statements
P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
Product Information
Purity
97%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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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.
• The mixed anhydride formed with carboxylic acids adds to imines to give ?-lactams: Synthesis, 63 (1982):
• 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).
• These are also formed in high yield by cyclization of ?-amino acids: Bull. Korean Chem. Soc., 12, 457 (1991).