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Merck
CN

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

Key Documents

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Product Name

Bis(2-oxo-3-oxazolidinyl)phosphinic chloride, ≥97.0% (AT)

InChI

1S/C6H8ClN2O5P/c7-15(12,8-1-3-13-5(8)10)9-2-4-14-6(9)11/h1-4H2

SMILES string

ClP(=O)(N1CCOC1=O)N2CCOC2=O

InChI key

KLDLRDSRCMJKGM-UHFFFAOYSA-N

assay

≥97.0% (AT)

form

solid

mp

191 °C (dec.) (lit.)

Quality Level

200

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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

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ8549
BCCF4821
BCBW5270
BCBN1979V
BCBH2761V

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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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