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02610

Sigma-Aldrich

Ethyl dimethylphosphonoacetate

technical, ≥90% (GC)

Synonym(s):

Ethoxycarbonylmethylphosphonic acid dimethylester, Phosphonoacetic acid P,P-dimethyl ethylester

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About This Item

Linear Formula:
(CH3O)2P(O)CH2COOC2H5
CAS Number:
311-46-6
Molecular Weight:
196.14
Beilstein:
1777603
EC Number:
206-222-6
MDL number:
MFCD00015677
UNSPSC Code:
12352108
PubChem Substance ID:
329747474
NACRES:
NA.22

grade

technical

Quality Level

100

Assay

≥90% (GC)

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.435 (lit.)
n20/D 1.435

bp

134 °C/10 mmHg (lit.)

density

1.188 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CP(=O)(OC)OC

InChI

1S/C6H13O5P/c1-4-11-6(7)5-12(8,9-2)10-3/h4-5H2,1-3H3

InChI key

HUNISAHOCCASGM-UHFFFAOYSA-N

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Application

Reactant for synthesis of:
  • Non-nucleoside inhibitors of HCV polymerase NS5B
  • Neuropeptide Y1 receptor antagonists
  • Alkenylcarboxylates from Horner-Wadsworth-Emmons reactions

Reactant for:
  • Enantioselective transfer hydrogenation for preparation of the C7-C14 fragment of ulapualide A
  • Intramolecular Michael reactions
  • Olefination of peptidyl aldehydes with stabilized ylides

Other Notes

Horner-Wittig reagent

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

210.2 °F - closed cup

Flash Point(C)

99 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
038526/1
38526/1

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Hans M Larsson et al.
PloS one, 9(2), e90006-e90006 (2014-03-04)
Although urothelial progenitor-like cells have been described in the human urinary tract, the existence of stem cells remains to be proven. Using a culture system that favors clonogenic epithelial cell growth, we evaluated and characterized clonal human urothelial cells. We
Marie-Anaïs Locquet et al.
Cells, 10(2) (2021-03-07)
Chordomas are rare, slow-growing tumors of the axial skeleton. These tumors are locally aggressive and refractory to conventional therapies. Radical surgery and radiation remain the first-line treatments. Despite these aggressive treatments, chordomas often recur and second-line treatment options are limited.
W.S. Wadsworth
Org. React., 25, 73-73 (1977)
Marjaana Rantala et al.
Bio-protocol, 8(13), e2899-e2899 (2018-07-05)
The hierarchical composition and interactions of the labile thylakoid protein complexes can be assessed by sequential 2D-native gel-electrophoresis system. Mild non-ionic detergent digitonin is used to solubilize labile protein super-and megacomplexes, which are then separated with first-dimension blue native polyacrylamide

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