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270954

Sigma-Aldrich

Tris(2,2,2-trifluoroethyl) phosphite

99%

Synonym(s):

Tris(2,2,2-trifluoroethoxy)phosphine

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About This Item

Linear Formula:
(CF3CH2O)3P
CAS Number:
370-69-4
Molecular Weight:
328.07
Beilstein/REAXYS Number:
1714041
MDL number:
MFCD00009902
UNSPSC Code:
12352100
PubChem Substance ID:
24856417
NACRES:
NA.22

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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.
Jiulin Wang et al.
Angewandte Chemie (International ed. in English), 53(38), 10099-10104 (2014-07-26)
Of the various beyond-lithium-ion batteries, lithium-sulfur (Li-S) batteries were recently reported as possibly being the closest to market. However, its theoretically high energy density makes it potentially hazardous under conditions of abuse. Therefore, addressing the safety issues of Li-S cells
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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