439320
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:
Molecular Weight:
189.93
NACRES:
NA.22
UNSPSC Code:
12352103
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3544189
Quality Level
assay
≥95.0%
mp
245-250 °C (lit.)
functional group
fluoro
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
Application
4-(Trifluoromethyl)phenylboronic acid can be used as a reactant in:
It can also be used as a reactant to prepare:
- 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
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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
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)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 439320-1G | 04061832246031 |
| 439320-5G | 04061832246048 |