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417548

Sigma-Aldrich

4-Chlorophenylboronic acid

95%

Sinónimos:

(p-Chlorophenyl)boronic acid, 4-Chlorobenzeneboronic acid, NSC 25408, p-Chlorobenzeneboronic acid

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About This Item

Fórmula lineal:
ClC6H4B(OH)2
Número de CAS:
1679-18-1
Peso molecular:
156.37
Beilstein/REAXYS Number:
2936346
EC Number:
216-845-5
MDL number:
MFCD00039137
UNSPSC Code:
12352103
PubChem Substance ID:
24866159
NACRES:
NA.22

assay

95%

mp

284-289 °C (lit.)

SMILES string

OB(O)c1ccc(Cl)cc1

InChI

1S/C6H6BClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H

InChI key

CAYQIZIAYYNFCS-UHFFFAOYSA-N

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Application

4-Chlorophenylboronic acid can be used as a reactant in:
  • Palladium-catalyzed direct arylation.
  • Cyclopalladation.
  • Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation.
  • Copper-mediated ligandless aerobic fluoroalkylation.
  • Pd-catalyzed arylative cyclization.
  • Ruthenium catalyzed direct arylation.
  • Ligand-free copper-catalyzed coupling reactions.
  • Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions.

It can also be used to prepare:
  • Substituted diarylmethylidenefluorenes via Suzuki coupling reaction.
  • Baclofen lactam by Suzuki coupling of a pyrrolinyl tosylate, followed by hydrogenation reaction.
  • Palladium(II) thiocarboxamide complexes as Suzuki coupling catalysts.
  • Biaryls by Suzuki reactions of aryl chlorides, bromides, and iodides with arylboronic acids.

Other Notes

Contains a varying amounts of anhydride

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

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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A Double Suzuki Approach for Synthesis of Substituted Diarylmethylidenefluorenes
C. V. Ramana, et al.
Synlett, 1, 127-128 (2007)
Franco Furlani et al.
Carbohydrate polymers, 208, 451-456 (2019-01-20)
Developing synthetic materials able to mimic micro- and macrorheological properties of natural networks opens up to novel applications and concepts in materials science. The present contribution describes an active network based on a semi-synthetic polymer, a lactitol-bearing chitosan derivative (Chitlac)
Immobilized palladium on surface-modified Fe3O4/SiO2 nanoparticles: as a magnetically separable and stable recyclable high-performance catalyst for Suzuki and Heck cross-coupling reactions
Du, Q.; et al.
Tetrahedron, 68, 3577-3584 (2012)
Copper-Mediated Aerobic Fluoroalkylation of Arylboronic Acids with Fluoroalkyl Iodides at Room Temperature
Qi, Q.; Shen, Q.; Lu, L.
Journal of the American Chemical Society, 134, 648-6551 (2012)
Elangovan Sindhuja et al.
Dalton transactions (Cambridge, England : 2003), 41(17), 5351-5361 (2012-03-09)
A simple route to synthesise palladium(II) complexes from the reaction of N-substituted pyridine-2-thiocarboxamide ligands and PdCl(2)(PPh(3))(2) has been developed. The new complexes are very soluble in common solvents and have been fully characterised (elemental analysis, FT-IR, (1)H, (31)P, (13)C-NMR), including
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