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791806

Sigma-Aldrich

Yu-Wasa Auxiliary

97%

Synonym(s):

2,3,5,6-Tetrafluoro-4-(trifluoromethyl)aniline, 2,3,5,6,α,α,α-Heptafluoro-p-toluidine

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About This Item

Linear Formula:
CF3C6F4NH2
CAS Number:
651-83-2
Molecular Weight:
233.09
Beilstein/REAXYS Number:
2657893
MDL number:
MFCD00091518
UNSPSC Code:
12352101
PubChem Substance ID:
329768293
NACRES:
NA.22

Quality Level

100

assay

97%

form

liquid

reaction suitability

reaction type: C-C Bond Formation
reagent type: catalyst
reaction type: C-H Activation

refractive index

n20/D 1.431 (lit.)
n20/D 1.432

bp

186 °C (lit.)

density

1.662 g/mL at 25 °C
1.687 g/mL at 25 °C (lit.)

functional group

fluoro

SMILES string

Nc1c(F)c(F)c(c(F)c1F)C(F)(F)F

InChI

1S/C7H2F7N/c8-2-1(7(12,13)14)3(9)5(11)6(15)4(2)10/h15H2

InChI key

FJOACTZFMHZHSC-UHFFFAOYSA-N

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Other Notes

Acidic amides are superior directing groups for promoting C-H activation reactions with both Pd(0)/PR3 and Pd(II) catalysts.

Used in the Preparation of
  • Lactams via palladium-catalyzed olefination of arylamides with benzylacrylate, followed by 1,4-conjugate addition
  • N-(fluorinated aryl)benzamides as substrates for regioselective C-H amination reactions with O-benzoylhydroxylamines
  • Substituted succinimides via palladium-catalyzed carbonylation of N-aryl amides
  • N-aryl cyclopropanecarboxamide substrates and various amino acid ligands for palladium-catalyzed C-H activation of cyclopropanes

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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

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL3917
MKCL3347
MKBR5477V

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Wasa, M;
Journal of the American Chemical Society, 132(11), 3680-3681 null
Palladium(0)-Catalyzed Alkynylation of C(sp3)-H Bonds
He, J.:
Journal of the American Chemical Society null
Eun Jeong Yoo et al.
Journal of the American Chemical Society, 133(20), 7652-7655 (2011-04-28)
C-H amination of N-aryl benzamides with O-benzoyl hydroxylamines has been achieved with either Pd(II) or Pd(0) catalysts. Furthermore, we demonstrate that secondary amines can be directly used with benzoyl peroxide in a one-pot procedure that proceeds via the in situ
Eun Jeong Yoo et al.
Journal of the American Chemical Society, 132(49), 17378-17380 (2010-11-19)
Pd(II)-catalyzed β-C(sp(3))-H carbonylation of N-arylamides under CO (1 atm) has been achieved. Following amide-directed C(sp(3))-H cleavage and insertion of CO into the resulting [Pd(II)-C(sp(3))] bond, intramolecular C-N reductive elimination gave the corresponding succinimides, which could be readily converted to 1,4-dicarbonyl
Masayuki Wasa et al.
Journal of the American Chemical Society, 133(49), 19598-19601 (2011-11-09)
Systematic ligand development has led to the identification of novel mono-N-protected amino acid ligands for Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes. A diverse range of organoboron reagents can be used as coupling partners, and the reaction proceeds under mild conditions.

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Yu Group – Professor Product Portal

The Yu program centers around the discovery of catalytic carbon–carbon and carbon–heteroatom bond forming reactions based on C–H activation. Target transformations are selected to enable 1) the use of simple and abundant starting materials such as aliphatic acids, amines and alcohols, and 2) disconnections that drastically shorten the synthesis of a drug molecule or a major class of biologically active compounds.

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