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B75956 Aldrich

4-Bromophenylboronic acid

≥95.0%

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

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Description

Other Notes

Contains varying amounts of anhydride

Packaging

5 g in glass bottle

Application

Reagent used for
• Palladium catalyzed Suzuki-Miyaura cross-couplings1
• Pd(II)-catalyzed diastereoselective conjugate additions2
• Palladium-catalyzed stereoselective Heck-type reaction of allylic esters with arylboronic acids3
• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence4
• Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides5
• Pd-catalyzed arylative cyclization of alkyne-tethered enals or enones via carbopalladation of alkynes6
• Copper-catalyzed cross-couplings7,8

Reagent used in Preparation of
• Gallate-based obovatol analogs with potential anti-tumor activity9
• Protein modulators and enzymatic and kinase inhibitors10,11

Price and Availability

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26
WGK Germany 
3
RTECS 
CY8650000

Protocols & Articles

Articles

Arylboronic Acids

Aldrich is pleased to present its complete selection of arylboronic acids, the building blocks of the Suzuki coupling experiment. Most arylboronic acids readily undergo dehydration reactions to give ...
Aldrich ChemFiles 2001, 1.1, 5.
Keywords: Building blocks, Coupling reactions, Dehydration reaction, Suzuki coupling

Boronic Acids

Most boronic acids readily undergo dehydration reactions to give a cyclic (trimer) anhydride. Our selection of boronic acids may contain varying amounts of this cyclic anhydride. Fortunately, the aci...
Aldrich ChemFiles 2007, 7.7, 3.
Keywords: Chemfiles, Coupling reactions, Dehydration reaction, Suzuki coupling

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. Suzuki-Miyaura cross-couplings of arenediazonium tetrafluoroborate salts with arylboronic acids catalyzed by aluminium hydroxide-supported palladium nanoparticles Li, X.; et al. Org. Biomol. Chem. 3rd ed., 10, 495-497, (2012)

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2. Mild and Ligand-Free Pd(II)-Catalyzed Conjugate Additions to Hindered γ-Substituted Cyclohexenones Jordan-Hore, J. A.; Sanderson, J. N.; Lee, A-L. Org. Lett. 10th ed., 14, 2508-2511, (2012)

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3. Palladium-Catalyzed Heck-Type Reactions of Allylic Esters with Arylboronic Acids or Potassium Aryltrifluoroborates Yao, B.; et al. Adv. Synth. Catal. 6th ed., 354, 1069-1076, (2012)

4. Tandem-type Pd(II)-catalyzed oxidative Heck reaction/intramolecular C-H amidation sequence: a novel route to 4-aryl-2-quinolinones Inamoto, K.; et al. Chem. Commun. (Camb.) 36th ed., 48, 4332-4334, (2012)

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5. Copper-Mediated Aerobic Fluoroalkylation of Arylboronic Acids with Fluoroalkyl Iodides at Room Temperature Qi, Q.; Shen, Q.; Lu, L. J. Am. Chem. Soc. 15th ed., 134, 6548-6551, (2012)

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6. Cationic Pd(II)-Catalyzed Highly Enantioselective Arylative Cyclization of Alkyne-Tethered Enals or Enones Initiated by Carbopalladation of Alkynes with Arylboronic Acids Shen, K.; Han, X.; Lu, X. Org. Lett. 7th ed., 14, 1756-1759, (2012)

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7. Ligand-free copper-catalyzed coupling of nitroarenes with arylboronic acids Zhang, J.; et al. Green Chem. 4th ed., 14, 912-916, (2012)

8. Glycerol as a recyclable solvent for copper-catalyzed cross-coupling reactions of diaryl diselenides with aryl boronic acids Ricordi, V. G.; et al. Green Chem. 4th ed., 14, 1030-1034, (2012)

9. Synthesis of obovatol derivatives and their preliminary evaluation as antitumor agents Lee, M.-S.; et al. Bull. Korean Chem. Soc. 28, 1601-1604, (2007)

10. Discovery, synthesis, and biological evaluation of novel SMN protein modulators. J. Xiao, et al., J. Med. Chem. 54, 6215-6233, (2011)

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11. Synthesis of 6-(het) ary Xylocydine analogs and evaluating their inhibitory activities of CDK1 and CDK2 in vitro Xiao, C.; et al. Bioorg. Med. Chem. 23th ed., 19, 7100-7110, (2011)

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Synthesis and characterization of 4-iodophenylboronic acid: a new enhancer for the horseradish peroxidase-catalyzed chemiluminescent oxidation of luminol. Kricka LJ, Cooper M, and Ji X Anal. Biochem. 240(1), 119-25, (1996)

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Carbonic anhydrase inhibitors. Inhibition of the fungal beta-carbonic anhydrases from Candida albicans and Cryptococcus neoformans with boronic acids. Alessio Innocenti et al Bioorg. Med. Chem. Lett. 19, 2642-5, (2009)

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Role of interferon-gamma against invasion by Toxoplasma gondii in a human monocytic cell line (THP1): involvement of the parasite's secretory phospholipase A2. Gómez Marín JE, Bonhomme A, Guenounou M, et al. Cell. Immunol. 169(2), 218-25, (1996)

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Aryl boronic acid inhibition of synthetic melanin polymerization. Jason M Belitsky et al Bioorg. Med. Chem. Lett. 20, 4475-8, (2010)

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Electron-capture, capillary column gas chromatographic determination of low-molecular-weight diols in serum. Needham LL, Hill RH, Orti DL, et al. J. Chromatogr. A 233, 9-17, (1982)

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Inhibition studies of soybean (Glycine max) urease with heavy metals, sodium salts of mineral acids, boric acid, and boronic acids. Kumar S and Kayastha AM J. Enzyme Inhib. Med. Chem. 25(5), 646-52, (2010)

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Beil. 16,IV,1668

IR-Spectra (3), 1553:C / IR-Spectra (2), 1327:H / NMR-Reference 2 (2), 1015:A / RegBook 1 (2), 3031:A / Structure Index 1, 479:C:6

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