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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

Quality Level

200

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)

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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Organic letters, 14(10), 2508-2511 (2012-05-02)
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