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417130

Sigma-Aldrich

Benzene-1,4-diboronic acid

≥95.0%

Synonym(s):

p-Phenylenediboronic acid, 1,4-Phenylenebisboronic acid, 1,4-Phenylenediboronic acid, p-Benzenediboronic acid, Benzene-1,4-diboronic acid, NSC 25410

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About This Item

Linear Formula:
C6H4[B(OH)2]2
CAS Number:
4612-26-4
Molecular Weight:
165.75
Beilstein/REAXYS Number:
2836921
MDL number:
MFCD00236018
UNSPSC Code:
12352103
PubChem Substance ID:
24866124
NACRES:
NA.22

assay

≥95.0%

form

powder

mp

>350 °C (lit.)

SMILES string

OB(O)c1ccc(cc1)B(O)O

InChI

1S/C6H8B2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4,9-12H

InChI key

BODYVHJTUHHINQ-UHFFFAOYSA-N

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Related Categories

application

Reagent used for
  • Externally initiated Kumada catalyst-transfer polycondensation
  • Suzuki-Miyaura cross-coupling reactions
  • Energy transfer processes in optoelectronic devices
  • Palladium-catalyzed sequential alkenylation and conjugate addition reactions
  • Scholl cyclizations

Reagent used in Preparation of
  • Crosslinkers and cross-linked core-shell nanoparticles by RAFT polymerization and palladium-catalyzed Suzuki coupling reaction
  • Fluorescence and solution-processable coordination polymers
  • Cyclotricatechylene based porous crystalline material for gas storage
  • Indolizine derivatives as OLEDs
  • Helically p-stacked thiophene-based copolymers with circularly polarized fluorescence
  • Novel organic semiconductors and applications in organic thin-film transistors
  • Highly twisted polycyclic aromatic hydrocarbons with unexptected reactivity

Other Notes

Contains varying amounts of anhydride

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Sigma-Aldrich

BCH00019

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Anirban Pradhan et al.
Angewandte Chemie (International ed. in English), 50(52), 12582-12585 (2011-11-08)
Let's twist! The Scholl reaction with quinquephenyl derivatives has been shown to have an unexpectedly strong preference for forming twisted, helicene aromatic polycycles, instead of their flat counterparts. This tendency is so strong that it will overcome even severe steric
Multifunctional electron-transporting indolizine derivatives for highly efficient blue fluorescence, orange phosphorescence host and two-color based white OLEDs
Wan, J.; et al.
Journal of Materials Chemistry, 22, 4502-4510 (2012)
Cyclotricatechylene based porous crystalline material: Synthesis and applications in gas storage
Yu, J-T.; et al.
Journal of Materials Chemistry, 22, 5369-5373 (2012)
Pd-catalyzed sequential C-C and C-N bond formations for the synthesis of N-heterocycles: exploiting protecting group-directed C-H activation under modified reaction conditions.
Byung Seok Kim et al.
Chemistry, an Asian journal, 6(8), 1952-1957 (2011-03-18)
Nikka Turangan et al.
Nanotechnology, 32(7), 075604-075604 (2020-09-17)
Rigid, freestanding covalent organic framework (COF-1) membranes have been synthesized from 1,4-benzenediboronic acid (BDBA) precursors using two different approaches: room temperature solvent-vapour annealing (SVA) and solvothermal annealing (SA). Characterization of films using Fourier-transform infrared (FTIR) spectroscopy, x-ray diffraction (XRD), and
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