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441627

Sigma-Aldrich

3-Bromophenylboronic acid

≥95%

Synonym(s):

3-Bromobenzeneboronic acid

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About This Item

Linear Formula:
BrC6H4B(OH)2
CAS Number:
89598-96-9
Molecular Weight:
200.83
MDL number:
MFCD00239386
UNSPSC Code:
12352103
PubChem Substance ID:
24867690
NACRES:
NA.22

Assay

≥95%

form

powder or crystals

mp

164-168 °C (lit.)

SMILES string

OB(O)c1cccc(Br)c1

InChI

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

InChI key

AFSSVCNPDKKSRR-UHFFFAOYSA-N

Application

Reactant involved in a variety of organic reactions including:
  • Oxidative cross coupling
  • Gold salt catalyzed homocoupling
  • 1,4-Addition reactions with α,β-unsaturated ketones
  • Enantioselective addition reactions
  • Suzuki-Miyaura coupling for synthesis of anthranilamide-protected arylboronic acids
  • C-H Functionalization of quinones

Other Notes

Contains varying amounts of anhydride

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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G K Surya Prakash et al.
Organic letters, 6(13), 2205-2207 (2004-06-18)
[reaction: see text] A mixture of nitrate salt and chlorotrimethylsilane is found to be an efficient regioselective nitrating agent for the ipso-nitration of arylboronic acids to produce the corresponding nitroarenes in moderate to excellent yields. High selectivity, simplicity, and convenience

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