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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.)

functional group

fluoro

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT5899
MKCV4414
MKCR3723
MKCM2383
MKCJ8405

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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)
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
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)
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)
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

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