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Sigma-Aldrich

4-(Trifluoromethyl)phenylboronic acid

≥95.0%

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Synonym(s):
α,α,α-Trifluoro-p-tolylboronic acid, 4-(Trifluoromethyl)benzeneboronic acid, [p-(Trifluoromethyl)phenyl]boronic acid
Linear Formula:
CF3C6H4B(OH)2
CAS Number:
Molecular Weight:
189.93
Beilstein/REAXYS Number:
3544189
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95.0%

mp

245-250 °C (lit.)

SMILES string

OB(O)c1ccc(cc1)C(F)(F)F

InChI

1S/C7H6BF3O2/c9-7(10,11)5-1-3-6(4-2-5)8(12)13/h1-4,12-13H

InChI key

ALMFIOZYDASRRC-UHFFFAOYSA-N

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Show Differences

1 of 4

This Item
417599471933471070
4-Methoxyphenylboronic acid ≥95.0%

417599

4-Methoxyphenylboronic acid

4-Iodophenylboronic acid ≥95.0%

471933

4-Iodophenylboronic acid

mp

245-250 °C (lit.)

mp

204-206 °C (lit.)

mp

326-330 °C (lit.)

mp

217-220 °C (lit.)

Application

4-(Trifluoromethyl)phenylboronic acid can be used as a reactant in:
  • Site-selective Suzuki-Miyaura cross-coupling reactions.
  • Palladium-catalyzed direct arylation reactions.
  • Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence.
  • Ruthenium catalyzed direct arylation.
  • Ligand-free copper-catalyzed coupling reactions.
  • Amination and conjugate addition reactions.
  • Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions.
  • Rhodium-catalyzed asymmetric 1,4-addition reactions.
  • Copper-catalyzed nitration reactions.
  • Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation.
  • Palladium catalyzed allylation reaction with allyl alcohols.
  • N-Arylation of imidazoles and amines in the presence of copper-exchanged fluorapatite as a catalyst.

It can also be used as a reactant to prepare:
  • Thiazole derivatives for printable electronics.
  • Terphenyl benzimidazoles as tubulin polymerization inhibitors.
  • Aryl ketones by cross-coupling reaction with acid chlorides.

Other Notes

Contains varying amounts of anhydride

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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