15140
Bis(2-oxo-3-oxazolidinyl)phosphinic chloride
≥97.0% (AT)
Synonym(s):
BOP-Cl, Phosphoric acid bis(2-oxooxazolidide) chloride
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About This Item
Empirical Formula (Hill Notation):
C6H8ClN2O5P
CAS Number:
Molecular Weight:
254.56
Beilstein:
3654596
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
≥97.0% (AT)
form
solid
mp
191 °C (dec.) (lit.)
SMILES string
ClP(=O)(N1CCOC1=O)N2CCOC2=O
InChI
1S/C6H8ClN2O5P/c7-15(12,8-1-3-13-5(8)10)9-2-4-14-6(9)11/h1-4H2
InChI key
KLDLRDSRCMJKGM-UHFFFAOYSA-N
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Application
Bis(2-oxo-3-oxazolidinyl)phosphinic chloride was used in the preparation of hexadepsipeptide.
Other Notes
Reagent for activating the carboxylic group, synthesis of amides ; Esters ; Peptides
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Corr. 1B
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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R.D. Tung et al.
Journal of the American Chemical Society, 107, 4342-4342 (1985)
Yanjie Xu et al.
Molecules (Basel, Switzerland), 10(1), 259-264 (2007-11-17)
Hexadepsipeptide 2, the precursor of Hirsutellide A (1), was synthesized in an overall yield of 45% from N-Boc-Me-Gly via three coupling reactions using dicyclohexylcarbodiimide (DCC), O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyl- uronium hexafluorophosphate (HATU) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl), respectively.
E.J. Corey et al.
Journal of the American Chemical Society, 104, 6818-6818 (1982)
S. Danishefsky et al
Tetrahedron Letters, 25, 4203-4203 (1984)
J. Cabre et al.
Synthesis, 413-413 (1984)
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