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417556

Sigma-Aldrich

4-Fluorophenylboronic acid

≥95%

Synonym(s):

(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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1 G
$29.09
5 G
$58.26
25 G
$115.00

About This Item

Linear Formula:
FC6H4B(OH)2
CAS Number:
1765-93-1
Molecular Weight:
139.92
Beilstein/REAXYS Number:
2829653
MDL number:
MFCD00039136
UNSPSC Code:
12352103
PubChem Substance ID:
24866160
NACRES:
NA.22

$29.09

List Price$36.50Save 20%
Web-Only Promotion

Available to ship onApril 22, 2025Details

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Quality Level

100

assay

≥95%

form

powder

mp

262-265 °C (lit.)

functional group

fluoro

SMILES string

OB(O)c1ccc(F)cc1

InChI

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

InChI key

LBUNNMJLXWQQBY-UHFFFAOYSA-N

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Application

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]

Other Notes

Contains varying amounts of anhydride

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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

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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)
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
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
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
View All Related Papers

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      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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    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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