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791806

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
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
329768293
MDL number:
MFCD00091518
Beilstein/REAXYS Number:
2657893
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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

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

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

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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Related Content

Yu Group – Prof. Product Portal

Yu program focuses on efficient C–H bond activation for drug synthesis, using simple starting materials.

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
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
Palladium(0)-Catalyzed Alkynylation of C(sp3)-H Bonds
He, J.:
Journal of the American Chemical Society null
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Global Trade Item Number

SKUGTIN
791806-1G04061832950679
791806-10G04061833332795