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405957

Sigma-Aldrich

Tris(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite

98%

Synonym(s):

Tris(2H-perfluoro-2-propyl) phosphite

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About This Item

Linear Formula:
[(CF3)2CHO]3P
CAS Number:
66470-81-3
Molecular Weight:
532.06
Beilstein:
2315565
MDL number:
MFCD00192561
UNSPSC Code:
12352100
PubChem Substance ID:
24865342
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.300 (lit.)

bp

130 °C (lit.)

density

1.69 g/mL at 25 °C (lit.)

SMILES string

FC(F)(F)C(OP(OC(C(F)(F)F)C(F)(F)F)OC(C(F)(F)F)C(F)(F)F)C(F)(F)F

InChI

1S/C9H3F18O3P/c10-4(11,12)1(5(13,14)15)28-31(29-2(6(16,17)18)7(19,20)21)30-3(8(22,23)24)9(25,26)27/h1-3H

InChI key

MJOVEPJSFHDSOJ-UHFFFAOYSA-N

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General description

Tris(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite (tris(1,1,1,3,3,3-hexafluoroisopropyl) phosphite) is a sterically hindered, weakly σ-donating and strongly π-accepting ligand. It can be prepared by the reaction of lithium salt of 1,1,1,3,3,3-hexafluoro-2-propoxide with PCl3. It reacts with nucleosides to form deoxyribonucleoside 3′-bis(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite units.

Application

Tris(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite (tris(1,1,1,3,3,3-hexafluoroisopropyl) phosphite) may be used in the following processes:
  • Preparation of new phosphonylating and coupling agents for the synthesis of oligodeoxyribonucleotides.
  • Preparation of nucleoside H-phosphonate units.
  • Synthesis of tetrakis(1,1,1,3,3,3-hexafluoroisopropoxy)(phenylthio)phosphorane by reacting with 1,1,1,3,3,3-hexafluoroisopropyl benzenesulfenate.

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Preparation and nuclear magnetic resonance studies of pentacoordinated phosphorus compounds containing hexafluoroisopropoxy groups.
Denney DB, et al.
The Journal of Organic Chemistry, 48(13), 2159-2164 (1983)
Stereoselective propargylation mediated by a chiral metal cluster: reactions of [(propargylium)Co2 (CO)5{P(OR)3}][BF4] with carbon nucleophiles.
Caffyn AJM and Nicholas KM.
Journal of the American Chemical Society, 115(14), 6438-6439 (1993)
O Sakatsume et al.
Nucleic acids research, 18(11), 3327-3331 (1990-06-11)
New phosphonylating and coupling agents for the synthesis of oligodeoxyribonucleotides via H-phosphonate approach have been developed. Tris(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite, prepared by the reaction of lithium salt of 1,1,1,3,3,3-hexafluoro-2-propoxide with PCl3, reacts with deoxyribonucleosides in the presence of a catalytic amount of
O Sakatsume et al.
Nucleic acids research, 17(10), 3689-3697 (1989-05-25)
The solid phase synthesis of oligoribonucleotides using the H-phosphonate approach and the 1-[(2-chloro-4-methyl)phenyl]-4-methoxypiperidin-4-yl (Ctmp) and dimethoxytrityl (DMTr) groups, respectively, for the protection of the 2'- and 5'-hydroxy functions is described. The use of a new reagent, tris-(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite for the
Synthesis of antisense oligodeoxyribonucleotide analogues by use of deoxyribonucleoside 3'-bis(1,1, 1,3,3,3-hexafluoro-2-propyl)phosphites as new key intermediates.
Hosaka H, et al.
Heteroatom Chem., 2(1), 197-204 (1991)

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