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B75956

Sigma-Aldrich

4-Bromophenylboronic acid

≥95.0%

Synonym(s):

(p-Bromophenyl)boronic acid, 4-Bromobenzeneboronic acid, 4-Bromophenylboric acid, p-Bromobenzeneboronic acid, p-Bromophenylboric acid, NSC 25407

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About This Item

Linear Formula:
BrC6H4B(OH)2
CAS Number:
5467-74-3
Molecular Weight:
200.83
Beilstein:
2936347
EC Number:
226-779-9
MDL number:
MFCD00002104
UNSPSC Code:
12352103
PubChem Substance ID:
24892010
NACRES:
NA.22

Assay

≥95.0%
95%

form

crystals

mp

284-288 °C (lit.)

SMILES string

OB(O)c1ccc(Br)cc1

InChI

1S/C6H6BBrO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H

InChI key

QBLFZIBJXUQVRF-UHFFFAOYSA-N

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Application

Reagent used for
  • Palladium catalyzed Suzuki-Miyaura cross-couplings
  • Pd(II)-catalyzed diastereoselective conjugate additions
  • Palladium-catalyzed stereoselective Heck-type reaction of allylic esters with arylboronic acids
  • Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence
  • Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides
  • Pd-catalyzed arylative cyclization of alkyne-tethered enals or enones via carbopalladation of alkynes
  • Copper-catalyzed cross-couplings

Reagent used in Preparation of
  • Gallate-based obovatol analogs with potential anti-tumor activity
  • Protein modulators and enzymatic and kinase inhibitors

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis of obovatol derivatives and their preliminary evaluation as antitumor agents
Lee, M.-S.; et al.
Bull. Korean Chem. Soc., 28, 1601-1604 (2007)
James A Jordan-Hore et al.
Organic letters, 14(10), 2508-2511 (2012-05-02)
Ligand-free cationic Pd(II) catalyst with NaNO3 as an additive is a highly active catalytic system for conjugate additions to sterically hindered γ-substituted cyclohexenones. More challenging γγ- and βγ-substrates also react well to produce products with quaternary centers in good dr.
Chuan Xiao et al.
Bioorganic & medicinal chemistry, 19(23), 7100-7110 (2011-11-01)
A series of purine nucleoside analogues bearing an aryl and hetaryl group in position 6 were prepared and their biological activities were assessed by in vitro CDK1/Cyclin B1 and CDK2/Cyclin A2 kinase assay. From the synthesized chemicals, three Xylocydine derivatives
Anna C Pham et al.
Journal of controlled release : official journal of the Controlled Release Society, 268, 400-406 (2017-11-04)
Phosphorylated tocopherols are a new class of lipid excipients that have demonstrated potential in pharmaceutical applications. Their ability to solubilise poorly water soluble drugs indicates their potential utility in improving bioavailability of drugs where solubility limits their bioavailability. In this
Xing Li et al.
Organic & biomolecular chemistry, 10(3), 495-497 (2011-11-22)
Suzuki-Miyaura cross-couplings of arenediazonium salts with arylboronic acids catalyzed by highly active aluminium hydroxide-supported palladium nanoparticles catalyst have been investigated for the first time. The reactions are performed at 25 °C in MeOH without any base and ligand to afford
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