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417548

Sigma-Aldrich

4-Chlorophenylboronic acid

95%

Synonym(s):

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

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About This Item

Linear Formula:
ClC6H4B(OH)2
CAS Number:
1679-18-1
Molecular Weight:
156.37
Beilstein:
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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Double Suzuki Approach for Synthesis of Substituted Diarylmethylidenefluorenes
C. V. Ramana, et al.
Synlett, 1, 127-128 (2007)
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)
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)
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)
Short synthesis of 4-aryl-3-pyrrolin-2-ones
Sarah J.P.Yoon-Miller, et al.
Tetrahedron Letters, 48, 827-830 (2007)
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