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417556

Sigma-Aldrich

4-Fluorophenylboronic acid

≥95%

Sinonimo/i:

(4-Fluorophenyl)boric acid, (4-Fluorophenyl)dihydroxyborane, (4-Fluorophenyl)dihydroxyboron, (p-Fluorophenyl)boric acid, 4-Fluorobenzeneboronic acid, p-Fluorobenzylboronic acid, p-Fluorophenylboronic acid, NSC 142683

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About This Item

Formula condensata:
FC6H4B(OH)2
Numero CAS:
1765-93-1
Peso molecolare:
139.92
Beilstein:
2829653
Numero MDL:
MFCD00039136
Codice UNSPSC:
12352103
ID PubChem:
24866160
NACRES:
NA.22

Saggio

≥95%

Forma fisica

powder

Punto di fusione

262-265 °C (lit.)

Stringa SMILE

OB(O)c1ccc(F)cc1

InChI

1S/C6H6BFO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
LBUNNMJLXWQQBY-UHFFFAOYSA-N

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Applicazioni

4-Fluorophenylboronic acid can be used as a reactant in coupling reactions with arenediazonium tetrafluoroborates, iodonium salts, and iodanes. It is also used to make novel biologically active terphenyls.

It can also be used as a reactant in:
  • Suzuki coupling using microwave and triton B catalyst.
  • Pd-catalyzed direct arylation of pyrazoles with phenylboronic acids.
  • Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles.
  • Cu-catalyzed Petasis reactions.
  • Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence.
  • Ruthenium catalyzed direct arylation.
  • Rh-catalyzed asymmetric conjugate additions.
  • Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids.
  • Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions.
  • Suzuki cross-coupling of tetrabromothiophene.
  • Palladium-catalyzed addition to nitriles.

Altre note

Contains varying amounts of anhydride

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302,H315,H319,H335

Classi di pericolo

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Sigma-Aldrich

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Yuvraj Satkar et al.
Frontiers in chemistry, 8, 563470-563470 (2020-11-17)
The chemoselective reaction of the C- followed by the O-centered naphthyl radicals with the more electron-deficient hypervalent bond of the diaryliodonium(III) salts is described. This discovered reactivity constitutes a new activation mode of the diaryliodonium(III) salts which enabled a one-pot
Suk-Ku Kang et al.
The Journal of organic chemistry, 61(14), 4720-4724 (1996-07-12)
The palladium-catalyzed cross-coupling reaction of iodinanes (iodonium salts and iodanes) with organoboron compounds to form carbon-carbon bonds was achieved at ambient temperature under aqueous conditions in the absence of base. Coupling of phenylboronic acid with diphenyliodonium tetrafluoroborate in the presence
J J Li et al.
Journal of medicinal chemistry, 39(9), 1846-1856 (1996-04-26)
A novel series of terphenyl methyl sulfones and sulfonamides have been shown to be highly potent and selective cyclooxygenase-2 (COX-2) inhibitors. The sulfonamide analogs 17 and 21 were found to be much more potent COX-2 inhibitors and orally active anti-inflammatory
Robin Frauenlob et al.
The Journal of organic chemistry, 77(9), 4445-4449 (2012-04-13)
We have developed a copper-catalyzed process for the coupling of aldehydes, amines, and boronic acids. This allows greater reactivity with simple aryl boronic acids and allows coupling reactions to proceed that previously failed. Initial mechanistic studies support a process involving
Microwave-enhanced triton B catalyzed Suzuki coupling reaction
Meshram, H. M.; et al.
Indian J. Chem. B, 51, 362-365 (2012)
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