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Sigma-Aldrich

Tris(2,2,2-trifluoroethyl) phosphite

99%

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Synonym(s):
Tris(2,2,2-trifluoroethoxy)phosphine
Linear Formula:
(CF3CH2O)3P
CAS Number:
370-69-4
Molecular Weight:
328.07
Beilstein:
1714041
MDL number:
MFCD00009902
UNSPSC Code:
12352100
PubChem Substance ID:
24856417
NACRES:
NA.22

Quality Level

100

Assay

99%

form

liquid

refractive index

n20/D 1.324 (lit.)

bp

130-131 °C/743 mmHg (lit.)

density

1.487 g/mL at 25 °C (lit.)

SMILES string

FC(F)(F)COP(OCC(F)(F)F)OCC(F)(F)F

InChI

1S/C6H6F9O3P/c7-4(8,9)1-16-19(17-2-5(10,11)12)18-3-6(13,14)15/h1-3H2

InChI key

CBIQXUBDNNXYJM-UHFFFAOYSA-N

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General description

Tris(2,2,2-trifluoroethyl) phosphite is an organophosphorus compound that is used as a ligand in organometallic chemistry to enhance labialization in metal clusters and as a substitutional equivalent for carbon monoxide. It is also used as an electrolyte additive to improve the electrochemical performance and as a co-solvent for nonflammable electrolytes in Li-ion batteries.

Application

Tris(2,2,2-trifluoroethyl) phosphite was used in the synthesis of N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide via the Arbuzov reaction with 2-bromo-N-methoxy-N-methylacetamide.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

235.4 °F

Flash Point(C)

113 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Samuel Fortin et al.
The Journal of organic chemistry, 67(15), 5437-5439 (2002-07-20)
The N-methoxy-N-methyl bis(2,2,2-trifluoroethyl)phosphonamide was easily obtained via the Arbuzov reaction with use of commercially available tris(2,2,2-trifluoroethyl)phosphite, 2-bromo-N-methoxy-N-methylacetamide, and KF/alumina. The reaction of bis(2,2,2-trifluoroethyl)phosphonate with several aldehydes demonstrates the versatility of the method, which gives Z-unsaturated amides in good yields.
Krzysztof Matyjaszewski et al.
Molecules (Basel, Switzerland), 26(2) (2021-01-14)
N-alkyl phosphoranimines were synthesized via the Staudinger reaction of four different alkyl azides with tris(2,2,2-trifluoroethyl) phosphite. N-adamantyl, N-benzyl, N-t-butyl, and N-trityl phosphoranimines were thoroughly characterized and evaluated as chain-capping compounds in the anionic polymerization of P-tris(2,2,2-trifluoroethoxy)-N-trimethylsilyl phosphoranimine monomer. All four

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