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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:
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.)

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

related product

Product No.
Description
Pricing

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

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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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