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439320

Sigma-Aldrich

4-(Trifluoromethyl)phenylboronic acid

≥95.0%

Synonym(s):

α,α,α-Trifluoro-p-tolylboronic acid, 4-(Trifluoromethyl)benzeneboronic acid, [p-(Trifluoromethyl)phenyl]boronic acid

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About This Item

Linear Formula:
CF3C6H4B(OH)2
CAS Number:
128796-39-4
Molecular Weight:
189.93
Beilstein:
3544189
MDL number:
MFCD00151855
UNSPSC Code:
12352103
PubChem Substance ID:
24867498
NACRES:
NA.22

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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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
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Viktor O Iaroshenko et al.
Organic & biomolecular chemistry, 10(15), 2955-2959 (2012-03-10)
A facile synthetic approach for the synthesis of 1,8-naphthyridine-4(1H)-one derivatives via a catalyst free and Pd-supported tandem amination sequence is developed and described. In a case of aliphatic amines reaction proceeds in a catalyst free mode, however anilines demand Pd-supported
Microwave-promoted cross-coupling of acid chlorides with arylboronic acids: a convenient method for preparing aromatic ketones
Viera Polackova, et al.
Tetrahedron, 62, 11675-11678 (2006)
Palladium(0)-catalyzed direct cross-coupling reaction of allyl alcohols with aryl- and vinyl-boronic acids
Hirokazu Tsukamoto, et al.
Chemical Communications (Cambridge, England), 1200-1201 (2004)
Efficient synthesis of arylated coumarins by site-selective Suzuki-Miyaura cross-coupling reactions of the bis(triflate) of 4-methyl-5,7-dihydroxy-coumarin
Eleya, N.; et al.
Synlett, 23, 223-226 (2012)
M Lakshmi Kantam et al.
The Journal of organic chemistry, 71(25), 9522-9524 (2006-12-02)
N-Arylation of imidazoles and amines with arylboronic acids was accomplished with copper-exchanged fluorapatite (CuFAP) in methanol at room temperature. The products N-arylimidazoles and N-arylamines were isolated in good to excellent yields. A variety of arylboronic acids were converted to the
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