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15140

Sigma-Aldrich

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:
68641-49-6
Molecular Weight:
254.56
Beilstein:
3654596
MDL number:
MFCD00010077
UNSPSC Code:
12352100
PubChem Substance ID:
57647324
NACRES:
NA.22

Quality Level

200

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

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

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

Certificates of Analysis (COA)

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S. Danishefsky et al
Tetrahedron Letters, 25, 4203-4203 (1984)
J. Cabre et al.
Synthesis, 413-413 (1984)
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)
R.D. Tung et al.
Journal of the American Chemical Society, 107, 4342-4342 (1985)
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