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439320

Sigma-Aldrich

4-(Trifluoromethyl)phenylboronic acid

≥95.0%

Sinónimos:

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

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About This Item

Fórmula lineal:
CF3C6H4B(OH)2
Número de CAS:
128796-39-4
Peso molecular:
189.93
Beilstein:
3544189
Número MDL:
MFCD00151855
Código UNSPSC:
12352103
ID de la sustancia en PubChem:
24867498
NACRES:
NA.22

Análisis

≥95.0%

mp

245-250 °C (lit.)

cadena SMILES

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

Clave InChI

ALMFIOZYDASRRC-UHFFFAOYSA-N

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Aplicación

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.

Otras notas

Contains varying amounts of anhydride

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H302

Clasificaciones de peligro

Acute Tox. 4 Oral

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

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Sigma-Aldrich

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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)
S Van Mierloo et al.
Magnetic resonance in chemistry : MRC, 50(5), 379-387 (2012-04-18)
Four 2,5-bis(5-aryl-3-hexylthiophen-2-yl)thiazolo[5,4-d]thiazole derivatives have been synthesized and thoroughly characterized. The extended aromatic core of the molecules was designed to enhance the charge transport characteristics, and solubilizing hexyl side chains were introduced on the thiophene subunits to enable possible integration of
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)
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