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274259

Sigma-Aldrich

Methyl P,P-bis(2,2,2-trifluoroethyl)phosphonoacetate

95%

Synonym(s):

Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate

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About This Item

Linear Formula:
CH3O2CCH2P(O)(OCH2CF3)2
CAS Number:
Molecular Weight:
318.11
Beilstein:
3594044
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Assay

95%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.370 (lit.)

density

1.504 g/mL at 25 °C (lit.)

SMILES string

COC(=O)CP(=O)(OCC(F)(F)F)OCC(F)(F)F

InChI

1S/C7H9F6O5P/c1-16-5(14)2-19(15,17-3-6(8,9)10)18-4-7(11,12)13/h2-4H2,1H3

InChI key

PVSJXEDBEXYLML-UHFFFAOYSA-N

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Application

Methyl P,P-bis(2,2,2-trifluoroethyl)phosphonoacetate can be used:
  • In one of the key synthetic steps for the preparation of trans-hydrindanes and (R)-(+)-umbelactone.
  • To prepare a cis-olefinic ester derivative by Still–Gennari olefination of an aldehyde derivative using 18-crown ether and potassium bis(trimethylsilyl)amide (KHMDS).
  • In the synthesis of (−)-(6S,2′S)-epi cryptocaryalactone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Sulfur-mediated intramolecular double Michael-type reaction: synthesis of trans-hydroindanes and mechanism
Ihara M, et al.
Journal of the Chemical Society. Perkin Transactions 1, 19, 2527-2535 (1992)
Journal of the Chemical Society. Perkin Transactions 1, 2527-2527 (1992)
Stereoselective total synthesis of (+)-(6R, 2′S)-cryptocaryalactone and (−)-(6S, 2′S)-epi cryptocaryalactone
Sabitha G, et al.
Tetrahedron, 64(44), 10207-10213 (2008)
First stereoselective total synthesis of pectinolide H
Ramesh D, et al.
Tetrahedron Letters, 53(10), 1258-1260 (2012)
An expedient synthesis of (R)-(+)-umbelactone
Gibson CL and Handa S
Tetrahedron Asymmetry, 7(5), 1281-1284 (1996)

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