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417556

Sigma-Aldrich

4-Fluorophenylboronic acid

≥95%

Sinónimos:

(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

Fórmula lineal:
FC6H4B(OH)2
Número de CAS:
1765-93-1
Peso molecular:
139.92
Beilstein:
2829653
Número MDL:
MFCD00039136
Código UNSPSC:
12352103
ID de la sustancia en PubChem:
24866160
NACRES:
NA.22
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Nivel de calidad

100

Ensayo

≥95%

Formulario

powder

mp

262-265 °C (lit.)

grupo funcional

fluoro

cadena SMILES

OB(O)c1ccc(F)cc1

InChI

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

Clave InChI

LBUNNMJLXWQQBY-UHFFFAOYSA-N

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Aplicación

4-Fluorophenylboronic acid can be used as a reactant in coupling reactions with arenediazonium tetrafluoroborates,[1] iodonium salts, and iodanes.[2] It is also used to make novel biologically active terphenyls.[3]

It can also be used as a reactant in:
  • Suzuki coupling using microwave and triton B catalyst.[4]
  • Pd-catalyzed direct arylation of pyrazoles with phenylboronic acids.[5]
  • Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles.[6]
  • Cu-catalyzed Petasis reactions.[7]
  • Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence.[8]
  • Ruthenium catalyzed direct arylation.[9]
  • Rh-catalyzed asymmetric conjugate additions.[10]
  • Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids.[11]
  • Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions.[12]
  • Suzuki cross-coupling of tetrabromothiophene.[13]
  • Palladium-catalyzed addition to nitriles.[14]

Otras notas

Contains varying amounts of anhydride

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H302,H315,H319,H335

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

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

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Certificados de análisis (COA)

Lot/Batch Number
SHBQ2160
05302MH
05402MH
03122KH
04214CH

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Cross-coupling of arenediazonium tetrafluoroborates with arylboronic acids catalysed by palladium
Sylvain Darses, et al.
Tetrahedron Letters, 37, 3857-3860 (1996)
Synthesis of tetraarylthiophenes by regioselective Suzuki cross-coupling reactions of tetrabromothiophene
Thanh Tuan Dang, et al.
Tetrahedron Letters, 48, 5, 845-847 (2007)
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
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
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
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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