Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

405957

Sigma-Aldrich

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

98%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

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

Quality Level

100

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCT5899
MKCV4414
MKCR3723
MKCM2383
MKCJ8405

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service