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B75956

Sigma-Aldrich

4-Bromophenylboronic acid

≥95.0%

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Synonym(s):
(p-Bromophenyl)boronic acid, 4-Bromobenzeneboronic acid, 4-Bromophenylboric acid, p-Bromobenzeneboronic acid, p-Bromophenylboric acid, NSC 25407
Linear Formula:
BrC6H4B(OH)2
CAS Number:
Molecular Weight:
200.83
Beilstein:
2936347
EC Number:
MDL number:
PubChem Substance ID:
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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1 of 4

This Item
417599471933417548
form

crystals

form

powder

form

-

form

-

mp

284-288 °C (lit.)

mp

204-206 °C (lit.)

mp

326-330 °C (lit.)

mp

284-289 °C (lit.)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

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

Signal Word

Warning

Hazard Statements

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

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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)
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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.
Erin Tay et al.
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Lipid based formulations (LBFs) are commonly employed to enhance the absorption of highly lipophilic, poorly water-soluble drugs. However, the utility of LBFs can be limited by low drug solubility in the formulation. Isolation of ionizable drugs as low melting, lipophilic
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
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

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